ISSN:
0170-2041
Keywords:
Tumor-associated antigens
;
Carbohydrates
;
Glycosyl trichloroacetimidates
;
Trichloroacetimidates
;
Alkylation, selective
;
Hapten synthesis
;
Antigens
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A versatile synthesis of the Gal-α-(1→3)-Gal-β-(1→4)-GlcNAc epitope coupled to an alkyl spacer molecule could be developed. The important building block 3′-allyl-D-lactal 6 was prepared in high yield by the action of dibutyltin oxide and allyl bromide on D-lactal and converted in several steps into the lactosamine derivative 13 with free 3′-OH group. Stereoselective glycosidation with the β-trichloroacetimidate of benzylated D-galactose 18 led to the trisaccharide in high yield. Activation of the protected Gal-α-(1→3)-Gal-β-(1→4)-GlcNAc derivative 21 by desilylation and trichloroacetimidate formation followed by glycosidation with ethyl 9-hydroxynonanoate furnished the spacer-bound trisaccharide hapten 24 in excellent yield after simple two-step deprotection. The trisaccharide hapten 24 can easily be used as immunogen after coupling to an immunogenic carrier.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1991199101113
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