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

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DOIResolve DOI: http://doi.org/10.1021/ja5114672
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TypeArticle
Journal titleJournal of the American Chemical Society
Volume137
Issue9
Pages32713275; # of pages: 5
AbstractJadomycin 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.
Publication date
PublisherACS Publications
LanguageEnglish
AffiliationNational Research Council Canada; Aquatic and Crop Resource Development
Peer reviewedYes
NRC number56149
NPARC number21275442
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Record identifier565aaf4c-202c-4bd1-9904-0c961a34c2e4
Record created2015-07-14
Record modified2016-05-09
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