Total Synthesis and Structural Revision of the Antibiotic Tetrapeptide GE81112A

Abstract

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.

Keywords: antibiotics; non-ribosomal peptide synthesis; peptides; structural revision; total synthesis.