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. 2015 Mar 11;137(9):3271-5.
doi: 10.1021/ja5114672. Epub 2015 Feb 26.

Eight-membered ring-containing jadomycins: implications for non-enzymatic natural products biosynthesis

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Eight-membered ring-containing jadomycins: implications for non-enzymatic natural products biosynthesis

Andrew W Robertson et al. J Am Chem Soc. .

Abstract

Jadomycin Oct (1) was isolated from Streptomyces venezuelae ISP5230 and characterized as a structurally unique eight-membered l-ornithine ring-containing jadomycin. The structure was elucidated through the semisynthetic derivatization of starting material via chemoselective acylation of the l-ornithine α-amino group using activated succinimidyl esters. Incorporation of 5-aminovaleric acid led to jadomycin AVA, a second eight-membered ring-containing jadomycin. These natural products illustrate the structural diversity permissible from a non-enzymatic step within a biosynthetic pathway and exemplifies the potential for discovery of novel scaffolds.

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