ja020257s_si_001.pdf (286.93 kB)
Mannopeptimycins, Novel Antibacterial Glycopeptides from Streptomyces hygroscopicus, LL-AC98
journal contribution
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. CarterA 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 (1−5), 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 3−5 are critical for retaining antibacterial potency.