Access to fluorescent probes via allyl glycosides: the synthesis of a Brucella trisaccharide epitope linked to a coumarin.
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-alpha-D-mannopyranosid e (6) was used as glycosyl donor in the preparation of the trisaccharide [alpha-D-Rha p4NFo-(1----2)-]2-alpha-D-Rha p4NFo-O-allyl (16). Thioglycoside 6 was activated with N-iodosuccinimide and triflic acid or by bromine in the glycosylations and the inhibitor 16 was obtained after deprotection by transesterification, reduction of the azido groups with hydrogen sulfide, and N-formylation with ethyl formate. Ozonolysis of the allyl glycoside in 16 and reductive amination with 7-amino-4-methylcoumarin then gave the target fluorescent trisaccharide conjugate.
Eichler
E
E
Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario.
Kihlberg
J
J
Bundle
D R
DR
D000498:Allyl Compounds / Q000737:chemistry*; D000942:Antigens, Bacterial / Q000032:analysis*; D002002:Brucella / Q000276:immunology*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003374:Coumarins / Q000737:chemistry*; D000939:Epitopes / Q000032:analysis; D005456:Fluorescent Dyes; D006027:Glycosides / Q000737:chemistry*; D008969:Molecular Sequence Data; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000276:immunology
D000498:Allyl Compounds; D000942:Antigens, Bacterial; D003374:Coumarins; D000939:Epitopes; D005456:Fluorescent Dyes; D006027:Glycosides; D014312:Trisaccharides