Eight-Membered Ring-Containing Jadomycins: Implications For Non-Enzymatic Natural Products Biosynthesis
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY(2015)
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 alpha-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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Key words
biosynthesis,eight-membered,ring-containing,non-enzymatic
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