Title: Flavine-Adenine Dinucleotide
CAS Registry Number: 146-14-5
CAS Name: Riboflavine 5￠-(trihydrogen diphosphate) 5￠?5￠-ester with adenosine
Synonyms: adenosine 5￠-(trihydrogen diphosphate) 5￠?5￠-ester with riboflavine; FAD; riboflavine 5￠-adenosine diphosphate; isoalloxazine-adenine dinucleotide
Trademarks: Fademin (Chugai); Flamitajin (Teisan; Iwaki); Flanin F (Tokyo Tanabe); Flavitan
Molecular Formula: C27H33N9O15P2
Molecular Weight: 785.55
Percent Composition: C 41.28%, H 4.23%, N 16.05%, O 30.55%, P 7.89%
Literature References: The prosthetic group of certain flavoproteins including D-amino acid oxidase, glucose oxidase, glycine oxidase, fumaric hydrogenase, histaminase, and xanthine oxidase. Isoln from yeast: Warburg
et al., Biochem. Z. 297, 417 (1938). Structure and isoln from liver, kidneys, hearts, muscles: Warburg, Christian,
ibid. 298, 150 (1938); isoln from the mycelium of
Eremothecium ashbyii: Yagi, Tada,
Biochem. Prep. 7, 51 (1959); Masuda
et al., US 2973305 (1961 to Takeda). Synthesis: Christie
et al., J. Chem. Soc. 1954, 46; Huennekens, Kilgour,
J. Am. Chem. Soc. 77, 6716 (1955); DeLuca, Kaplan,
J. Biol. Chem. 223, 569 (1956); Moffatt, Khorana,
J. Am. Chem. Soc. 80, 3756 (1958).
Review: A. Holmgren,
Experientia 36 (Suppl), 149-180 (1980). Review of FAD and other flavin coenzymes: Beinert,
The Enzymes vol. 2, P. D. Boyer
et al., Eds. (Academic Press, New York, 2nd ed., 1960) pp 339-416;
see also vol. XIII Part B (Academic Press, New York, 3rd ed., 1975), several authors.
Derivative Type: Barium salt
Molecular Formula: C27H31BaN9O15P2
Molecular Weight: 920.86
Percent Composition: C 35.22%, H 3.39%, Ba 14.91%, N 13.69%, O 26.06%, P 6.73%
Properties: Small yellow spheres clustered like grapes. Absorption max: 366, 445 nm. The absorption curve is practically identical with that of riboflavine. There is some stronger absorption between 450 and 510 nm resulting in aq solns which are more reddish and less green than those of riboflavine. The appearance of a strong greenish fluorescence indicates decomposition and loss of catalytic activity.
Absorption maximum: Absorption max: 366, 445 nm
