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

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 Saito deoxygenation reaction as key step. 13c does not inhibit the transglycosylase (PBP 1b), a key enzyme in the biosynthesis of bacterial peptidoglycan. The result demonstrates the importance of this OH group for the binding of disaccharide moenomycin analogues to the enzyme.