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US 10,870,710 B2Granted
Synthetic oligosaccharide subunits of the Psl exopolysaccharide of pseudomonas aeruginosa and uses thereof
AssigneesMedImmune, LLC, University of Georgia Research Foundation, Inc.
InventorsAntonio DiGiandomenico, Qun Wang, Charles K. Stover, Geert-Jan Boons, Kai-For Mo, Huiqing Li
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Abstract
This disclosure relates to synthetic oligosaccharide subunits of the Pseudomonas exosaccharide Psi and uses thereof, e.g., for epitope mapping of anti-Psl antibodies, for identification of anti-Psl antibodies, and for use as vaccines. In one aspect a synthetic oligosaccharide subunit of a Pseudomonas aeruginosa Psl oligosaccharide is provided, comprising the trisaccharide of formula I.
Claims7
A method comprising
- (a) reacting a thiomannosyl donor 7 with acceptor
- saccharide 10 to form disaccharide 13, and then partially deprotecting disaccharide 13 to form disaccharide 14:
- (b) reacting disaccharide 14 and with thiomannoside 8
- to form trisaccharide 15 then partially deprotecting the trisaccharide to form compound 16,
- then reacting compound 16 with CC13 CN, and Cs2 CO3, in dichloromethane to form the trichloroacetimidate trisaccharide 17:
- and
- (c) reacting the trichloroacetimidate trisaccharide 17 with compound 12
- in the presence of trimethylsilyl trifluoromethanesulfonate and dichloromethane at −30° C. to form a linear tetrasaccharide 18
- then partially deprotecting linear tetrasaccharide 18 with hydrofluoric acid in pyridine to form the linear tetrasaccharide 19:
- and wherein Nap is 2-methylnaphthyl, Ph is a phenyl group, Bn is a benzyl group, Bz is a benzoyl group, All is allyl ether, and TBS is t-butyldimethylsilyl.
7 more elements
Dependencies are inferred from the claim text.