Total Synthesis and Structural Revision of the Antibiotic Tetrapeptide GE81112A.

Gerrit Jürjens,Sören M M Schuler,Michael Kurz,Sylvain Petit,Cédric Couturier, Frédéric Jeannot,Fabian Nguyen,Raffael C Wende,Peter E Hammann,Daniel N Wilson,Eric Bacqué,Christoph Pöverlein,Armin Bauer

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION（2018）

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摘要

The total synthesis of the naturally occurring antibiotic GE81112A, a densely functionalized tetrapeptide, is reported. Comparison of spectral data with those of the natural product and the lack of biological activity of the synthesized compound led us to revise the published configuration of the 3-hydroxypipecolic acid moiety. This hypothesis was fully validated by the synthesis of the corresponding epimer.

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关键词

antibiotics,non-ribosomal peptide synthesis,peptides,structural revision,total synthesis

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