A

Co py rig hte dM ate ria l

CHEMICAL STRUCTURE AND FUNCTIONAL GROUPS
Functional Groups

RNH2

R2C NH imine

R-C( O)NH-R amide

amine ROH

R-C( O)-H aldehyde

R-C( O)R ketone

R-C( O)-OH

alcohol

carboxylic acid

R-C( O)-OH ester RSH thiol

RSR

RSSR

R-(C O)-SR thiol ester

sulfide

disulfide

CH3CH3 alkane

CH2 CH2 alkene

HC CH alkyne

HO P O

phosphate

OR

R C H

OR

acetal

Copyright 2000 by The McGraw-Hill Companies

RO P O

RO P OR

RO P OR

phosphomonoester

phosphodiester

OR

phosphotriester

OR

OH

OH

R C R

ketal

R C H

R C R

OR

OR

OR

hemiacetal

hemiketal

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Appendix

285

R-groups

Co py rig hte dM ate ria l

C CH3
acetyl CO 2

VITAMINS1
Name
Biotin

Cobalamins (B12)

Ascorbic acid

Folic acid

Nicotinamide

Pyridoxal (B6)

CR
acyl

OH

NH2

hydroxyl

amino

carboxyl

CH2

NH

N H

benzyl

phenyl

imidazole

indole

Structural Feature
O

Reactions

most transfers of CO2 pyruvate carboxylase

HN

NH

methylmalonyl-CoA mutase (odd-chain fatty acid metabolism) methionine synthesis

Co

HO

OH

hydroxylation of proline and lysine in collagen/elastin synthesis nor-adrenaline synthesis

OR

glutamate O

deoxy-TMP synthesis from deoxy-UMP; required for DNA synthesis purine and pyrimidine synthesis one-carbon metabolism

O H

N2

NH2

oxidations and reductions throughout metabolism (NADH, NADPH)

OR

PO

transaminases, decarboxylases, epimerases; almost everyting to do with amino acid metabolism

The structures of the vitamins and cofactors shown in this table are not complete structures. Only the functional parts of the molecules are shown.

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286

Basic Concepts in Biochemistry

VITAMINS (Cont.)

Co py rig hte dM ate ria l

Coenzyme A BIG STRUCTURESH fatty acid synthesis and oxidation; carries groups at acyl (acid) oxidation state

HO NH OH

Pantothenate

O O

a part of coenzyme A; youll never see it alone

(i.e., CoA-S

R)

Riboflavin

R N N

cofactor for oxidation and reduction

succinate dehydrogenase TCA

transfer of

CH3

Thiamine

S N R(big)

pruvate dehydrogenase -ketoglutarate dehydrogenase (TCA)

POPO

HMP-pathwaytransaldolase and transketolase

Lipoic acid

S S

oxidations and reductions and acyl transfer pyruvate dehydrogenease -ketoglutarate dehydrogenase

Vitamin A (retinoic acid)

and so on

visual pigment and other, unknown functions

Vitamin E ( -tocopherol)

lipid-soluble antioxidant to protect membranes

HO

Vitamin K

carboxylation at glutamate residues in proteins of blood clotting system to create Ca2 binding site

etc.

Copyright 2000 by The McGraw-Hill Companies

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