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The full structures of three chromomycins, A2, A3 and A4

โœ Scribed by M. Miyamoto; Y. Kawamatsu; K. Kawashima; M. Shinohara; K. Nakanishi


Publisher
Elsevier Science
Year
1966
Tongue
French
Weight
293 KB
Volume
7
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The chromomycins are a group of cancerostatic antibiotics produced by Streptomyces griseus 1) and are undoubtedly closely related to olivomycin 2) and several other antibiotics 3, isolated by various groups.

  1. The principal constituent, chromomycin A3@) is commercially available , while chromomycin A2(a and chromomycin A4(A) are the major byproducts isolated during the manufacture of As. The structures of these three constituents are reported in this communication.

The three chromomycins 5) can be isolated by silica gel chromatography of the chromomycin A mixture using ethyl acetate containing 1% oxalic acid as the solvent, the ratio of A 2, A3 and A4 being roughly 1:8:1.

11 Chromomvcin A3 (1)

A planar structure _4 had previously been derived 6) for chromomycin A3 on grounds of a 11 tetrasaccharide n that was isolated from the alkaline hydrolysate of its "methyl ether!' m. p. 185'. However, subsequent 545


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The structure of the chromophore chromomyclnone was deduced as Indicated in the following scheme. Chromomrcin A3 1 CH3COOH, boil 2 hrs Chromomvcinone (CHR) UV same as chromomycin A5 :. Chromophore still intact. Chromomycinone No.34 m.p. 183-135', having a typical naphthoquinone UV spectrum, A",izH 2