Access to fluorescent probes via allyl glycosides: the synthesis of aBrucella trisaccharide epitope linked to a coumarin |
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Authors: | Eva Eichler Jan Kihlberg David R Bundle |
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Institution: | (1) Institute for Biological Sciences, National Research Council of Canada, K1A 0R6 Ottawa, Ontario, Canada |
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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- -d-mannopyranoside (6) was used as glycosyl donor in the preparation of the trisaccharide -d-Rhap4NFo(1 2)-]2- -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.Issued as NRCC 31913. |
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Keywords: | glycoside synthesis allyl glycoside fluorescent probe Brucella common epitope reductive amination |
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