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Synthesis of microcolin analogs using trimethylsilylated lactams

✍ Scribed by Ralph-Heiko Mattern; Sarath P. Gunasekera; Oliver J. McConnell

Book ID: 104256705
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 330 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00336-5

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✦ Synopsis

The synthesis of microcohn analogs is described using an approach that could be of considerable practical interest for structure-activity studies on microcolin and related peptides. This synthetic pathway is more efficient than the methods reported to date, and allows the variation of the Xaa-pyrrolin-2-one unit of these molecules. which has been shown to be crucial for the biological activity. 0 1997 Elsevier Science Ltd. Microcolin A and B, two lipopeptides isolated from the blue-green alga Lyngbya mqjuscula expressed potent cytotoxicity and immunesuppressive properties. ' Recently, we have reported the synthesis of an analog of microcolin B.* Microcolin A:R=OH d Microcolin B:R=H

The synthesis of the Pro-pyrrolin-2-one unit was achieved by acylation of Meldrum's acid with Boc-

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