Sarkomycin
Title: Sarkomycin
CAS Registry Number: 11031-48-4
Additional Names: Sarcomycin
Literature References: Antibiotic and antitumor substance produced by Streptomyces erythrochromogenes, strain W-115-C, from soil found at Kamakura, Japan: Umezawa et al., J. Antibiot. 6A, 101, 147, 153 (1953); eidem, Antibiot. Chemother. 4, 514 (1954). Structure of sarkomycin A, the active principle: Hooper et al., ibid. 5, 585 (1955). Characterization of sarkomycins A, A¢ and B: Maeda, Kondo, J. Antibiot. 11A, 37 (1958). Sarkomycin reacts with H2S to form sarkomycins S1, S2 and S3: Tatsuoka et al., ibid. 9B, 107, 110 (1956). Structure of S1 and S2: eidem, ibid. 11B, 275 (1958). Synthesis of d- and l-sarkomycin A: Toki, ibid. 10A, 35, 226 (1957). Synthesis of dl-sarkomycin A: Toki, Bull. Chem. Soc. Jpn. 30, 450 (1957); R. K. Boeckman, Jr. et al., J. Org. Chem. 45, 752 (1980); J. N. Marx, G. Minaskanian, ibid. 47, 3306 (1982); B. A. Wexler et al., ibid. 3333; A. P. Kozikowski, P. D. Stein, J. Am. Chem. Soc. 104, 4023 (1982). Abs config of A: Sato et al., Chem. Pharm. Bull. 11, 829 (1963). Revised config of A: Hill et al., J. Org. Chem. 32, 2330 (1967). Review: S. A. Waksman, H. A. Lechevalier, The Actinomycetes vol. III (Williams & Wilkins, Baltimore, 1962) pp 362-364; Sung in Antibiotics vol. I, D. Gottlieb, P. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 156-165.
Properties: Oily liquid. [a]D15 -32.5° (c = 1 in methanol). uv max (water): 230 nm. Sol in water, methanol, ethanol, butanol, ethyl acetate. Sparingly sol in petr ether.
Optical Rotation: [a]D15 -32.5° (c = 1 in methanol)
Absorption maximum: uv max (water): 230 nm
 
Derivative Type: Sarkomycin A
CAS Registry Number: 489-21-4
CAS Name: (R)-2-Methylene-3-oxocyclopentanecarboxylic acid
Molecular Formula: C7H8O3
Molecular Weight: 140.14
Percent Composition: C 59.99%, H 5.75%, O 34.25%

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