Synthesis and transglycosylase-inhibiting properties of a disaccharide analogue of moenomycin A lacking substitution at C-4 of unit F

Authors
Riedel, S Donnerstag, A Hennig, L Welzel, P Richter, J Hobert, K Muller, D van Heijenoort, J
Citation
S. Riedel et al., Synthesis and transglycosylase-inhibiting properties of a disaccharide analogue of moenomycin A lacking substitution at C-4 of unit F, TETRAHEDRON, 55(7), 1999, pp. 1921-1936
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
7
Year of publication
1999
Pages
1921 - 1936
Database
ISI
SICI code
0040-4020(19990212)55:7<1921:SATPOA>2.0.ZU;2-A
Abstract
A disaccharide analogue (A4 = 13c) of moenomycin A lacking the OH group in the 4-position of the uronic acid moiety has been synthesized using the Sai to deoxygenation reaction as key step. 13c does not inhibit the transglycos ylase (PBP 1b), a key enzyme in the biosynthesis of bacterial peptidoglycan . The result demonstrates the importance of this OH group for the binding o f disaccharide moenomycin analogues to the enzyme. (C) 1999 Elsevier Scienc e Ltd. All rights reserved.