• A P P E N D I X •

CHEMICAL STRUCTURE AND FUNCTIONAL GROUPS

Functional Groups

RNH2 R2CNH R-C(O)NH-R

amine imine amide

ROH R-C(O)-H R-C(O)R R-C(O)-OH

alcohol aldehyde ketone carboxylic acid

R-C(O)-OH
ester

RSH RSR RSSR R-(CO)-SR

thiol sulfide disulfide thiol ester

CH3CH3 CH2CH2 HCCH

alkane alkene alkyne

O O O O
—
—
—

—
—

—
—

HO — P — O RO — P — O RO — P — OR RO — P — OR
—

—
—

O O O OR
phosphate phospho- phospho- phospho-
monoester diester triester

OR OR OH OH
—

—
—

R —C— H R —C — R R —C— H R —C— R

—

—
—

OR OR OR OR

acetal ketal hemiacetal hemiketal

284

BG McGraw-Hill: Gilbert, Basic Concepts in Biochemistry, JN 5036

Appendix • 285 •

R-groups

O O
—
—

—
—
— C — CH3 —C—R OH NH2
acetyl acyl hydroxyl amino
CO
2

carboxyl

CH2 —
— N NH
N
H
benzyl phenyl imidazole indole

VITAMINS1
Name Structural Feature Reactions
Biotin O most transfers of CO2 pyruvate carboxylase

HN NH

S
Cobalamins methylmalonyl-CoA mutase
(B12) (odd-chain fatty acid metabolism)
Co
methionine synthesis

hydroxylation of proline and lysine

O O HO OH
Ascorbic acid in collagen/elastin synthesis

OR nor-adrenaline synthesis

deoxy-TMP synthesis from deoxy-UMP;

Folic acid N required for DNA synthesis
N glutamate
N
purine and pyrimidine synthesis
—
—

N O
O
one-carbon metabolism

O O oxidations and reductions

Nicotinamide H H throughout metabolism
N2 NH2 (NADH, NADPH)
N OR N

R R
Pyridoxal H O transaminases, decarboxylases, epimerases;
(B6)  almost everyting to do with amino acid
O
PO metabolism
N
1
The structures of the vitamins and cofactors shown in this table are not complete structures.
Only the functional parts of the molecules are shown.

BG McGraw-Hill: Gilbert, Basic Concepts in Biochemistry, JN 5036

• 286 • Basic Concepts in Biochemistry

VITAMINS (Cont.)
Pantothenate O a part of coenzyme A;

—— ——

—
HO ——— NH — you’ll never see it alone


—
O
OH
Coenzyme A BIG STRUCTURE—SH fatty acid synthesis and oxidation; carries
groups at acyl (acid) oxidation state
O

—
(i.e., CoA-S R)
R
Riboflavin cofactor for oxidation and reduction
N N
succinate dehydrogenase – TCA
N
O
O transfer of
CH3
Thiamine pruvate dehydrogenase
S N — R(big) -ketoglutarate dehydrogenase (TCA)
POPO
HMP-pathway—transaldolase and
transketolase

Lipoic acid S S oxidations and reductions and acyl

transfer – pyruvate dehydrogenease
-ketoglutarate dehydrogenase

Vitamin A visual pigment and other, unknown

(retinoic acid) and so on functions

Vitamin E lipid-soluble antioxidant to protect

(-tocopherol) O membranes

HO

Vitamin K O carboxylation at glutamate residues in

proteins of blood clotting system to create
Ca2 binding site
etc.
O

BG McGraw-Hill: Gilbert, Basic Concepts in Biochemistry, JN 5036