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4a_ Vitamins and Nutrition

VIEWS: 3 PAGES: 11

									Vitamins and Nutrition

Vitamin –

         Coenzyme –


         Cofactor –


         Prosthetic group –


Water-Soluble Vitamins
Name                  Function                                          Deficiency
Vitamin B1            Precursor to coenzyme thiamin                     Beriberi – muscle weakness, loss of
(thiamin)             pyrophosphate, which is required for oxidative    reflexes, numbness, depression
                      decarboxylation reactions
Vitamin B2            Precursor to FAD and FMN, which are               Not named – photophobia,
(riboflavin)          prosthetic groups used for redox reactions.       proliferation of capillaries in the eye,
                                                                        dermatitis
Vitamin B3            Precursor to NAD and NADP, which are              Pellegra – weight loss, digestive
(niacin)              coenzymes used for redox reactions.               disorders, dermatitis, depression,
                                                                        dementia
Vitamin B5            Precursor to Coenzyme A                           Not named – neurological and
(Pantothenic acid)                                                      digestive problems
Vitamin B6            Precursor to pyridoxal phosphate, which is a      Not named – dermatitis, neuropathy,
(pyridoxal and        prosthetic group for amino acid metabolic         altered free amino acid levels,
related               enzymes and for glycogen phosphorylase            depression.
compounds)
Vitamin B12           Precursor to coenzymes used for one-carbon        Pernicious anemia – enlarged fragile
(cobalamin)           transfer reactions                                erythrocytes, neurological disorders
Folic acid            Precursor to coenzyme tetrahydrofolate, which     Megaloblastic anemia – enlarged
                      is used for one-carbon transfer reactions         fragile erythrocytes, neural tube
                                                                        defects, neurological disorders
Biotin                Prosthetic group for several carboxylase          Not named – depression,
                      enzymes                                           hallucinations, muscle pain,
                                                                        dermatitis, immunodeficiency
Vitamin C             Coenzyme for hydroxylase enzymes                  Scurvy – defective collagen synthesis,
(ascorbic acid)                                                         dementia

Fat-Soluble Vitamins
Name                 Function                                               Deficiency
Vitamin A            Precursor visual pigment retinal and to retinoic       Not named – night-blindness,
(retinol and β-      acid signaling molecules involved in cellular          blindness, developmental
carotene)            differentiation                                        abnormalities, keratinization of
                                                                            epithelial tissues.
Vitamin D               Precursor to 1α , 25-dihydroxyvitamin D, a          Rickets and Osteomalacia –
(ergocalciferol and     signaling molecule involved in calcium absorption   softening of the bones
cholecalciferol)        and homeostasis, and in regulation of cellular
                        differentiation
Vitamin E               Antioxidant, especially in erythrocytes.            Not named – anemia, and possibly
(α-tocopherol)                                                              other effects
Vitamin K               Precursor to Vitamin K coenzyme used for            Hemorrhagic disease of the
(menadione and          synthesis of γ-carboxyglutamate residues,           newborn, Hemorrhagic syndrome –
related compounds)      especially in clotting factor proteins              deficient blood clotting
Niacin (Vitamin B3)

                                                                          O
                                                    HNO3
                                          N                                   OH
                                          CH3
          Nicotine        N                                       N       Nicotinic acid


          H                                           NH
  O       N                                                                                         O
              NH2
                                  O                                                                     NH2
                                              NH3                                                   Nicotinamide
                  Isoniazid       O                                                          N
      N

                                              O                                                      O

                                                  NH2                                                    NH2

                                      N                                                         N
                      CH2 O                                                   CH2 O



                        OH        OH                                               OH       OH

                              NH2                                                      NH2
              O                                                       O
                                      N                                                         N
      O P O              N                                        O P O            N
              O                       N                               O                         N
                              N                                             N
      O P O CH2                                                   O P O CH2 O
                              O
              O                                                     O


                        OH        OH                                               OH       O
                                                                               O P O
              Nicotinamide adenine                       Nicotinamide adenine
                                                                                 O
                  dinucleotide                         dinucleotide 2´-phosphate
                     [NAD]                                      [NADP]
                                                    2 electrons
                              H       O                  +                    H H       O
                                                     1 proton
                                          NH2                                               NH2

                              N                                               N
                              R                                               R
                                                2 electrons
                         Oxidized                    +                    Reduced
                         NAD(P)                  1 proton                 NAD(P)H
Alcohol Dehydrogenase

        His67                                                                                           His67

                                                         His51                                                                                             His51
    HN                                     Ser48                                                     HN
                          Cys174                                                                                              Cys174
Cys46                                                                                           Cys46
             N                                                                                                N
                                       OH                 NH                                                                           Ser48                NH
                          S                                                                                               S
    S                                                N                                               S                                                 N
                Zn                                                                                              Zn
                                                                                                                                   O
                                                                                                                                       H
                                                                                                                      H                            O H
                     H                                                    Substrate                               O
                 O                                                         binding                                    H                                OH
                                                                                                         H3C C                     N
                 H                                                                                                                         O
                                                                                                                  H H
                                                                                                                                               R
                                                                                                                          O        NH2


                                                                                                                          Proton
                                                                                                                          abstraction
         His67                                                                                          His67

                                                              His51                                                                                        His51
        HN                                                                                           HN
                                  Cys174                                                                                      Cys174
 Cys46                                                                                          Cys46
                 N                                                                                            N
                                           Ser48               NH                                                                      Ser48                NH
                              S                                                                                           S
        S                                                 N                                          S                                                 N
                 Zn                                                                                             Zn
                                       O           H                              Hydride                                          O           H
                                   H                      H                       transfer                                     H                       H
                                                     O                                                                                             O
                     O                                                                                            O
                                                          OH                                                          H                                OH
            H3C C                      N                                                                 H3C C                     N
                                             O                                                                                             O
                     HH                                                                                           H H
                          H                      R                                                                                             R
                              O        NH2                                                                                O        NH2


                                                         Substrate
                                                         dissociation

                                                                 His67

                                                                                                            His51
                                                               HN                            Ser48
                                                                                  Cys174
                                                         Cys46
                                                                      N
                                                                                           OH                NH
                                                                                  S
                                                               S                                        N
                                                                         Zn

                                                                              H
                                                                          O
                                                                          H
Riboflavin (Vitamin B2)

                        O                                         O                                        O
H3C           N                            H3C            N                      H3C               N
                            NH                                        NH                                       NH

H3C           N       N          O         H3C            N       N     O        H3C               N       N     O
                        OH                                        OH                                       OH

         HO                                         HO                                       HO
                      OH                                          OH                                       OH
                                                                                                                        NH2
                     OH                                       O                                        O
                                                                                                                              N
                                                         O P O                                     O P O            N
                                                              O                                        O                      N
                                                                                                             N
                                                                                                   O P O CH2 O
                                                                                                     O
            Riboflavin                                 Flavin                             Flavin adenine
           (Vitamin B2)                             mononucleotide                         dinucleotide             OH       OH
                                                       [FMN]                                  [FAD]




Isoalloxazine Ring
                                     1 electron                                   1 electron
                      O                   +                       H     O              +                         H       O
                                      1 proton                                     1 proton
H3C           N                                   H3C             N •                           H3C              N
                            NH                                              NH                                                NH

H3C           N       N      O                    H3C             N     N    O                  H3C              N       N        O
              R              1 electron                           R          1 electron                          R       H
                                  +                                               +
                              1 proton                                        1 proton
       Fully oxidized                                   Partially reduced                                  Fully reduced




Ascorbic Acid (Vitamin C)
                                                    2 electrons
                                                         +
                                                     2 protons
                  OH                                                                        OH
      HO                    O          O                                         HO                    O        O


                  HO                 OH                   2 electrons                          O            O
                                                               +
                  Ascorbic acid                            2 protons                      Dehydroascorbic acid
                  (Vitamin C)
Thiamin (Vitamin B1)

                NH2                     H                                                                     NH2               H              Thiamin pyrophosphate
                                                     Thiamin
          N                       N                  (Vitamin B1)                                        N              N
                                             S                                                                                       S                  O           O
H3C             N        H3C                         OH                                      H3C              N   H3C                          O P O P O
                                                                                                                                                        O           O


                                                                                                                                           HO
                                 Thiamin pyrophosphate                                       Thiamin pyrophosphate                                              Hydroxyethyl
          NH2            H                                            NH2                    carbanion                          NH2             C
                                                                                                                                                    CH3         Thiamin pyrophosphate
                                                                                     C
      N              N                                           N               N                                          N              N
                             S          O        O                                       S           O        O                                     S           O       O
H3C       N    H3C                 O P O P O               H3C        N    H3C                   O P O P O           H3C        N    H3C                    O P O P O
                                        O        O                                                   O        O                                                 O       O
                                                                                 +                                                    +
                                                                                 O                                                   CO2
                                                                     Pyruvate
                                                                                 C       O       +   H
                                                                          H3C        C
                                                                                     O




Pantothenic Acid (Vitamin B5)
                                                                                                 NH2                                                            NH2
                                                                                                             N                                                              N
                                                                                             N                                                              N

                                                               O            O                    N           N                  O          O                    N           N
Pantoic                  OH
                                                           O P O P O CH2 O                                               O P O P O CH2 O
 acid                    CH2
                                                                 O          O                                                   O          O
                H3C C CH3
                                                                 CH2                                                            CH2
                HO CH                                                                        OH          OH                                                 OH       OH
                                                         H3C C CH3                                                   H3C C CH3
                    O C
                                                         HO CH                                                          HO CH
                         NH             O
!-alanine                                                  O C                                                           O C
                     H2C CH2 C OH                                                                                                                                               O
                                                               NH               O                                               NH             O
                                                                                  H                                                              H           C
                                                           H2C CH2              C N CH2 CH2 SH                              H2C CH2            C N CH2 CH2 S   CH3
                Pantothenic Acid
                                                                          Coenzyme A                                                Acetyl Coenzyme A
                  (Vitamin B5)                                             (CoA-SH)                                                    (Acetyl-CoA)




Biotin
      O                                                    O               Carboxylase                                  O       O                  Carboxybiotin
                     Biotin
                                                                           prosthetic group                             C
HN            NH                                      HN       NH                                                   O       N         NH
                                    O                                                    O                                                                      O
H               H                                    H               H                                                  H                  H
                                                                                                     Lys-Enzyme                                                             Lys-Enzyme
                                            OH                                                N                                                                     N
      S         H                                          S         H                                                           S         H
                                                                                              H                                                                     H
Folic Acid


H2N           N            N                              Folic Acid
                                        p-Amino
      HN
                           N            benzoic                                 O
                                        acid
              O                    HN
                                                                                     O
          N5                                                    H
                                                                N
                   N10                                                          Glutamate
                                                            O
                                                                O           O

                                                                                                H                                                                           H
                                   NADPH                   NADP                                         H NADPH                     NADP                                                H
              N        N                                              H2N            N          N        H                                       H2N            N           N            H

  HN                                                                        HN                                                                           HN                              H
                       N                Dihydrofolate                                           N                        Dihydrofolate                                      N
                                          reductase                                                                        reductase
              O                 HN                                                   O                  HN                                                      O           H       HN
                                        R                                                                      R                                                                              R

                                                                                                                                                           Tetrahydrofolate
      Folic Acid                                                            Dihydrofolate
                                                                                                                                                                (THF)




Cobalamin (Vitamin B12)
                                                                                                                                                            HO
                                                                                                                                                                                    N
                                                                                                                                                     HO
                                                                                                                                                                            N             N

                               N                                                                                                                                    O
                                                                                                                                                                                N         NH2
          O       NH2                                                       O    NH2                                                    O    NH2
                               C       NH2                                                    CH3       NH2                                               CH2       NH2

                                            O                                                             O                                                             O
                                                      O                                                             O                                                               O
H2N                                                             H2N                                                           H2N

                   N               N                      NH2                        N          N                       NH2                      N          N                           NH2
      O                                                                 O                                                           O
       NH2                 Co3+                                         NH2                  Co3+                                   NH2                  Co3+
                   N               N                                                 N              N                                            N              N
 O                                                                  O                                                          O
                                                NH2                                                           NH2                                                           NH2
          O                                                                 O                                                           O
                                                  O                                                             O                                                               O
  HN                                                                HN                                                          HN
                        N                                                                N                                                           N
          O       HO N                                                      O    HO N                                                   O    HO N
      O P O                                                             O P O                                                       O P O
          O                                                                 O                                                           O
                       O                                                                 O                                                           O
                               Cyanocobalamin
                                                                                         Methylcobalamin                                             5´-Deoxyadenosylcobalamin
              HO                (Vitamin B12)                                   HO                                                          HO
Vitamin B6
           O                             HO                                    H2N
               CH                                CH2                                 CH2
     HO                                 HO                                  HO
                          OH                              OH                                    OH

               N                        CH3     N                           CH3      N
     CH3
               H                                H                                    H

          Pyridoxal                          Pyridoxine                        Pyridoxamine



                                                                       O
                                                               R
                                                                           O
     O                                                             N
          CH
                          O                                            CH
HO                                                                                   O
                      O P O                                HO
                                                                                   O P O
                          O
          N                                                                          O
CH3                                                                    N
                                                               CH3
          H
                                                                       H
     Pyridoxal phosphate
                                                                   Pyridoxal phosphate
                                                                   Schiff base to !-amino acid




          R                                                    R
          C O         +        H 2N R                           C N R          +         H 2O
          R                                                    R
      Aldehyde                 Amine                            Schiff
         or                                                     base
       ketone
Aminotransferases
               O                                                                                                O
                                              O       O                                                                                   O         O
                   O                                                                                                O
 O                                 H3N                                                      H3N                                       O
                       +                                       Aspartate
                                                                                                                        +
                                                            aminotransferase
 O         O                             O        O                                                 O       O                         O        O

!-Ketoglutarate                         Aspartate                                                   Glutamate                    Oxaloacetate



               O                                                                                                    O

                   O                                                                                                    O
 O                                   H3N                                                            H3N                                   O
                           +                                     Alanine
                                                                                                                            +
                                                             aminotransferase
 O         O                             O        O                                                     O       O                         O         O

!-Ketoglutarate                          Alanine                                                        Glutamate                     Pyruvate




                                          !-amino
                                O         acid
                                     H                                     O                                                     O
                                 C           R                                  H                                                    H
     Enzyme                O                                Enzyme          C       R                       Enzyme               C        R
                                                                       O                                                  O
                               H        NH2                                                                             NH2
                                                                       H
                                                                                 NH                                                   NH
           N                                                       N
       H       CH                                             H        CH                                                       CH
                                    O                                                       O                                                   O
      HO                                                     HO                                                     HO
                               O P O                                                O P O                                                  O P O
                                    O                                                       O                                                   O
     H3C       N                                            H3C        N                                            H3C     N
               H                                                       H                                                    H
                                                                                                                                     Loss of
                               !-keto                                                                                                !-carbon
                       O       acid                                                                                                  proton
                       C        R
                   O                                                            O                                                O
Enzyme                                                                                                      Enzyme
                           O                              Enzyme                C       R                                        C         R
                                                                           O                                            NH2 O
                      NH3                                                           NH                                  H                NH
       NH2                                                                                                                      CH
                   CH2                                        NH2          CH2                                                                  O
                                     O                                                          O                   HO
       HO                                         Hydrolysis HO                                                                            O P O
                                O P O                                                 O P O
                                     O                                                          O                                               O
      H3C          N                                          H3C      N                                            H3C     N

                   H                                                   H                                                    H
Serine Hydroxymethyl Transferase

                H                                 OH                                           H     N5,N10-Methylene
H2N        N    N                                                              H2N         N   N
                                          H3N     CH2                                                Tetrahydrofolate         H3N
  HN                                 +                                                HN                                  +
                N                                              Serine                          N
                H                            O    O         hydroxymethyl                                                          O    O
           O        HN                                       transferase                   O   H2C    N
                                p-amino                                                                    p-amino
      Tetrahydrofolate          benzamide-    Serine                                  Tetrahydrofolate     benzamide-              Glycine
           (THF)                glutamate                                                  (THF)           glutamate




                                    Serine
                            O       OH
                                H                                   O        OH                                   O           OH
                            C       CH2                                 H                                             H
Enzyme              O                              Enzyme           C        CH2               Enzyme             C           CH2
                                                                O                                            O
                         H       NH2
                                                                H
                                                                         NH                                           NH
       N                                                    N                                         NH2
  H        CH                                          H        CH                                            CH
                             O                                                    O                                                 O
 HO                                                    HO                                             HO
                        O P O                                                O P O                                            O P O
                             O                                                    O                                                 O
H3C        N                                       H3C          N                                    H3C      N
           H                                                    H                                             H

                                                                                                      Loss of              N5,N10
                                                                                                      R-group             Methylene
                             Glycine                                                                                        THF
                    O
                        H                                       O
                    C           H                                   H                                             O
Enzyme          O                            Enzyme             C       H                      Enzyme
                                                            O                                                     C           H
                         NH3                                                                                 O
                                                                    NH                                                NH
       N                                          NH2                                                 NH2
  H        CH                                               CH                                                CH2
                             O                                                O                                                     O
 HO                                               HO                                                  HO
                        O P O                                               O P O                                             O P O
                             O        Product                                 O       Protonation                                   O
H3C        N                        dissociation H3C        N                         of !-carbon H3C         N
           H                        (Schiff base            H                                                 H
                                     exchange)
Vitamin K

        O            Menaquinone-7
                      (Vitamin K2)




        O


        O                                                                        O
                      Phylloquinone
                       (Vitamin K1)                                                        Menadione
                                                                                           (Vitamin K3)

        O                                                                        O




            O                                          O   O
Glutamate
                O                                  O C         O
   H                                               H
   N                                               N
                    CO2 + O2                               !-carboxy-
                                                           glutamate
   O                                               O          (Gla)


                         !-glutamyl
                         carboxylase




       OH                                              O

                        Vitamin K                          O
                          Cycle
                R                                          R
       OH                                              O
            Vitamin K                  Vitamin K
            epoxide                    epoxide
            reductase                  reductase                                          O     O
                                O



                                                                        Warfarin           OH       O
                                       R                                (Wisconsin Alumni
                                O                                       Research Foundation)
Vitamin D
       Cholesterol                                                                                   Pre-Vitamin D

                                           dehydrogenase                                     h!


HO                                               HO                                           HO
                                                      7-Dehydrocholesterol

                                                                                                               h!




                                                                          OH     1) 25-hydroxylase
                                   1",25-Dihydroxy-
                                      vitamin D3                                 2) 1"-hydroxylase


                                                                                                                  Cholecalciferol
                                               HO           OH                                       HO           (Vitamin D3)




Vitamin A

                                       OH
                                                                                   !-Carotene
               Retinol
               (Vitamin A)

                                   O                                                O

                                       H                                                OH

               all-trans-Retinal                                 all-trans-Retinoic acid



                                                                                                      9-cis-Retinoic acid
                                                                                                                            O   OH




     11-cis-Retinal
                        O     H




Vitamin E
                                                  O


                               HO                            !-Tocopherol
                                                             (Vitamin E)

								
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