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

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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-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.

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Authors and Affiliations

  1. Institute for Biological Sciences, National Research Council of Canada, K1A 0R6, Ottawa, Ontario, Canada

    Eva Eichler, Jan Kihlberg & David R. Bundle

Authors
  1. Eva Eichler
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  2. Jan Kihlberg
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  3. David R. Bundle
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Issued as NRCC 31913.

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Eichler, E., Kihlberg, J. & Bundle, D.R. Access to fluorescent probes via allyl glycosides: the synthesis of aBrucella trisaccharide epitope linked to a coumarin. Glycoconjugate J 8, 69–74 (1991). https://doi.org/10.1007/BF00731014

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  • DOI: https://doi.org/10.1007/BF00731014

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