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Mannopeptimycins, Novel Antibacterial Glycopeptides from Streptomyces hygroscopicus, LL-AC98

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posted on 2002-07-26, 00:00 authored by Haiyin He, R. Thomas Williamson, Bo Shen, Edmund I. Graziani, Hui Y. Yang, Subas M. Sakya, Pete J. Petersen, Guy T. Carter
A series of novel antibiotics with activity against methicillin-resistant staphylococci and vancomycin-resistant enterococci has been purified, and their structures have been characterized using spectroscopic analyses and chemical conversions. These antibiotics, designated mannopeptimycins α−ε (15), are glycosylated cyclic hexapeptides containing two stereoisomers of an unprecedented amino acid, α-amino-β-[4‘-(2‘-iminoimidazolidinyl)]-β-hydroxypropionic acid (Aiha), as a distinguishing feature. The cyclic peptide core of these antibiotics is attached to a mannosyl monosaccharide moiety in 2 and to mannosyl monosaccharide and disaccharide moieties in 1, 3, 4, and 5. The presence and position of an isovaleryl group in the terminal mannose (Man-B) in 35 are critical for retaining antibacterial potency.

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