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

Article abstract of DOI:10.1016/S0040-4020(98)01225-3

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.