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The Chemistry of the Antibiotics Chrysomycin A and B. Antitumor Activity of Chrysomycin A

U Weiss, K Yoshihira, R J Highet, R J White, T T Wei

J Antibiot (Tokyo). 1982 Sep;35(9):1194-201.

PMID: 7142022

Abstract:

The yellow antibiotic chrysomycin, isolated in crystalline form in 1955, is found to consist of two closely related components, a major one, chrysomycin A, and a minor one, chrysomycin B. They differ only through the replacement of a vinyl group of chrysomycin A by methyl in chrysomycin B. The absorption spectrum of chrysomycin A is identical with that of the antitumor antibiotic toromycin (gilvocarcin V, 2064A), while that of chrysomycin B is similarly identical with the one of gilvocarcin M (2064B). The structures of these antibiotics (toromycin, the glivocarcins, and 2064A and B) have been elucidated recently. Chrysomycins A and B thus contain the same chromophores as gilvocarcins V and M, respectively; comparison of 1H and 13C NMR spectra confirms this identity. The chrysomycins differ from these other antibiotics in the C-glycosidic side-chain, which is a methylpentose in the gilvocarcins, a 3,5-dimethylpentose in the chrysomycins. Structure and relative configuration of the latter are given. The biological activity and possible biosynthesis of the chrysomycins are discussed.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP83852566 Chrysomycin B Chrysomycin B 83852-56-6 Price
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