Title: NAD
CAS Registry Number: 53-84-9
CAS Name: Adenosine 5￠-(trihydrogen diphosphate)
P￠?5￠-ester with 3-(aminocarbonyl)-1-b-D-ribofuranosylpyridinium inner salt
Synonyms: 3-carbamoyl-1-b-D-ribofuranosylpyridinium hydroxide 5￠?5￠-ester with adenosine 5￠-(trihydrogen pyrophosphate) inner salt; nicotinamide-adenine dinucleotide; diphosphopyridine nucleotide; DPN; cozymase; coenzyme I; Co I; codehydrogenase; b-NAD; NAD+; nadide
Molecular Formula: C21H27N7O14P2
Molecular Weight: 663.43
Percent Composition: C 38.02%, H 4.10%, N 14.78%, O 33.76%, P 9.34%
Literature References: One of the biologically active forms of nicotinic acid,
q.v. Occurs in living cells primarily in the oxidized state. Serves as a coenzyme of the dehydrogenases, especially in the dehydrogenation of primary and secondary alcohols. NAD usually acts as a hydrogen acceptor, forming NADH which then serves as a hydrogen donor in the respiratory chain. Isoln from erythrocytes: O. Warburg, W. Christian,
Biochem. Z. 287, 291 (1936); from rabbit muscle: S. Ochoa,
ibid. 292, 68 (1937); from yeast: H. v. Euler, F. Schlenk,
Z. Physiol. Chem. 246, 64 (1937); G. A. LePage,
J. Biol. Chem. 168, 623 (1947);
Biochem. Prep. 1, 28 (1949). Manuf by fermentation:
GB 1190079 (1970 to Kyowa),
C.A. 73, 54631g (1970). Synthetic approach: N. A. Hughes
et al., J. Chem. Soc. 1957, 3733. Nomenclature: M. Dixon,
Science 132, 1548 (1960). Occurs in 2 forms, a-NAD and b-NAD, distinquished by the configuration of the ribosyl nicotinamide linkage. Only the b-anomer is bioactive. Stereochemistry: R. U. Lumieux, J. W. Lown,
Can. J. Chem. 41, 889 (1963). NMR studies: N. J. Oppenheimer
et al., Proc. Natl. Acad. Sci. USA 68, 3200 (1971); R. H. Sarma, R. J. Mynott,
Chem. Commun. 1972, 977; M. Blumenstein, M. A. Raftery,
Biochemistry 11, 1643 (1972). Biosynthesis:
Nutr. Rev. 30, 139 (1972); J. W. Foster, A. G. Moat,
Microbiol. Rev. 44, 83 (1980). Combined bioluminescent assay of NAD and NADH: M. T. Karp, P. I. Vuorinen,
Methods Enzymol. 122, 147 (1986).
Review: "Niacin: Nicotinic Acid, Nicotinamide, NAD(P)" in
Vitamins, W. Friedrich, Ed. (Walter de Gruyter, Berlin, 1988) pp 473-542.
Properties: Very hygroscopic white powder. Freely sol in water without residue. A 1% soln has a pH of ~2. Aq solns are stable for ~1 week. [a]D20 -31.5° (c = 1.2 in water). uv max: 260 nm (e 18100).
Optical Rotation: [a]D20 -31.5° (c = 1.2 in water)
Absorption maximum: uv max: 260 nm (e 18100)
Derivative Type: Reduced form
CAS Registry Number: 58-68-4
Synonyms: NADH; DPNH; 1,4-dihydronicotinamide adenine dinucleotide
Molecular Formula: C21H29N7O14P2
Molecular Weight: 665.44
Percent Composition: C 37.90%, H 4.39%, N 14.73%, O 33.66%, P 9.31%
Properties: uv max: 260, 340 nm (e 15000, 6290).
Absorption maximum: uv max: 260, 340 nm (e 15000, 6290)
