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A Highly Efficient Synthetic Strategy for Polymeric Support Synthesis of Le x , Le y , and H‐type 2 Oligosaccharides
Author(s) -
Zhu Tong,
Boons GeertJan
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010601)7:11<2382::aid-chem23820>3.0.co;2-2
Subject(s) - chemistry , linker , protecting group , oligosaccharide , glycosyl , combinatorial chemistry , stereochemistry , biochemistry , organic chemistry , computer science , alkyl , operating system
The O‐protecting groups Levulinoyl (Lev) and 9‐fluroenylmethoxycarbonyl (Fmoc) offer an attractive set of orthogonal protecting groups which are compatible with base sensitive N ‐trichloroethoxylcarbonyl (Troc) group. By exploiting these orthogonal protecting groups and a novel phenolic ester linker, a series of oligosaccharide of biological importance, Le x , H‐type 2, and Le y , were synthesized on the polytheylene glycol resin MPEG ( M W 5000). The products bearing a p ‐hydroxybenzyl group could be easily converted into glycosyl donors for further synthesis. Using this strategy, a spacer containing tumor antigen Le y ‐Lac hexasaccharide was described. The artificial spacer at the reducing end provides an opportunity for selective conjugation to an appropriate carrier protein for immunlogical studies.