Tetrahedron

Modular synthesis of diphospholipid oligosaccharide fragments of the bacterial cell wall and their use to study the mechanism of moenomycin and other antibiotics

CM Gampe, H Tsukamoto, TSA Wang, S Walker…

Index: Gampe, Christian M.; Tsukamoto, Hirokazu; Wang, Tsung-Shing Andrew; Walker, Suzanne; Kahne, Daniel Tetrahedron, 2011 , vol. 67, # 51 p. 9771 - 9778

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Citation Number: 26

Abstract

We present a flexible, modular route to GlcNAc–MurNAc-oligosaccharides that can be readily converted into peptidoglycan (PG) fragments to serve as reagents for the study of bacterial enzymes that are targets for antibiotics. Demonstrating the utility of these synthetic PG substrates, we show that the tetrasaccharide substrate lipid IV (3), but not the disaccharide substrate lipid II (2), significantly increases the concentration of moenomycin ...