Title: 6-Diazo-5-oxo-L-norleucine
CAS Registry Number: 157-03-9
Additional Names: DON
Molecular Formula: C6H9N3O3
Molecular Weight: 171.15
Percent Composition: C 42.11%, H 5.30%, N 24.55%, O 28.04%
Line Formula: N2CHCOCH2CH2CH(NH2)COOH
Literature References: Antitumor antibiotic produced by an unidentified species of Streptomyces from Peruvian soil: Dion et al., J. Am. Chem. Soc. 78, 3075 (1956); Ehrlich et al., Antibiot. Chemother. 6, 487 (1956). Several methods of synthesis: De Wald, Moore, ibid. 80, 3941 (1958); eidem, US 2965634 (1960 to Parke, Davis). Review: Pittillo, Hunt, Antibiotics vol 1, D. Gottlieb, P. D. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 481-493.
Properties: Pale yellow crystals from dil ethanol, dec 145-155°. [a]D26 +21° (c = 5.4). uv max (phosphate buffer): 244, 275 nm (E1%1cm 376, 683). Freely sol in water. The pH of aq solns should be maintained between 4.5 and 6.5. Also sol in aq solns of methanol, ethanol, acetone. Sparingly sol in absolute alcs.
Optical Rotation: [a]D26 +21° (c = 5.4)
Absorption maximum: uv max (phosphate buffer): 244, 275 nm (E1%1cm 376, 683) |