Access to fluorescent probes via allyl glycosides: the synthesis of aBrucella trisaccharide epitope linked to a coumarin

Abstract

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.

DOI: 10.1007/BF00731014

Cite this paper

@article{Eichler1991AccessTF, title={Access to fluorescent probes via allyl glycosides: the synthesis of aBrucella trisaccharide epitope linked to a coumarin}, author={Eva E Eichler and Jan Kihlberg and David R. Bundle}, journal={Glycoconjugate Journal}, year={1991}, volume={8}, pages={69-74} }