Infect lmmun 57:2829-36
- DR Bundle, JW Cherwonogrodzky, MAJ Gidney, J Meikle P, MB Perry, T Peters
Oligosaccharide allyl glycosides are demonstrated to provide a route to fluorescent probes and simple inhibitors. Ethyl 2-O-acetyl-4-azido-3-O-benzoyl-4,6-dideoxy-1-thio-α-d-mannopyranoside (6) was used as glycosyl donor in the preparation of the trisaccharide [α-d-Rhap4NFo(1 → 2)-]2-α-d-Rhap4NFo-O-allyl (16). Thioglycoside6 was activated withN-iodosuccinimide and triflic acid or by bromine in the glycosylations and the inhibitor16 was obtained after deprotection by transesterification, reduction of the azido groups with hydrogen sulfide, andN-formylation with ethyl formate. Ozonolysis of the allyl glycoside in16 and reductive amination with 7-amino-4-methylcoumarin then gave the target fluorescent trisaccharide conjugate.