Streptomyces murayamaensis

Figure 7.23 shows the prototype diazobenzo[Z ]fluorene-based natural products kinamycin A and prekinamycin. The kinamycin A-D family were first isolated from Streptomyces murayamaensis, but the structures were incorrectly characterized as having a cyanobenzo[Z ]carbazole ring. Since the initial discovery of the kinamycins, many new analogues have been discovered from natural sources.88-92... 

Cone, M. C. Seaton, R J. Halley, K. A. Gould, S. J. New products related to kinamycin from Streptomyces murayamaensis. I. Taxonomy, production, isolation and biological properties. J. Antibiot. 1989, 42, 179-188. 

Prekinamycin (35), like kinamycins A-F, was isolated from Streptomyces murayamaensis. Carbazole 33, a regioisomer of 7-deoxyprekinamycin (34), was synthesized in only four steps utilizing Pd(OAc), promoted oxidative cyclization as the pivotal step [27]. Similar to Furukawa s approach, the anilino-l,4-naphthoquinone 32 was obtained via Michael addition of the corresponding 2-methoxy-4-methyl-aniline to 1,4-naphthoquinone. Oxidative cyclization proceeded in 84% yield. 

An mCyN unit is also present in the core of the polyketide antibiotic asukamycin from Streptomyces nodosas subsp. asukaensis [96]. This has been shown to arise not from a variant of the shikimate pathway, but from the condensation of a C4 unit from the TCA cycle, closely related to succinate, with a C3 unit, possibly dihydroxyacetone phosphate, from the triose pool. Related studies concerning 3-amino-4-hydroxybenzoic acid biosynthesis in Streptomyces murayamaensis mutants MC2 and MC3 support this hypothesis [97]. 

The kinamycins (6), antibiotics produced by Streptomyces murayamaensis, are composed of a partially reduced carbazole nucleus.A purple compound isolated in small quantities from the same species is believed to have the structure 7 on basis of spectroscopic data. Compounds similar to 7 are proposed as biosynthetic precursors of the kinamycins. 3 ... 

Isol. from Streptomyces murayamaensis. Mp 133-136° dec. Structs. revised in 1994. 

Metab. from Streptomyces murayamaensis. Orange-yellow cryst. 

Metab. of Streptomyces murayamaensis. Precursor of Kinamycin F, K-30025. Purple solid. Mp 300° dec. Struct, revised in 1994. 

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