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Synthesis of Clustered Glycoside–Antigen Conjugates by Two One‐Pot, Orthogonal, Chemoselective Ligation Reactions: Scope and Limitations
Author(s) -
Grandjean Cyrille,
GrasMasse Hélène,
Melnyk Oleg
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(20010105)7:1<230::aid-chem230>3.0.co;2-l
Subject(s) - conjugate , scope (computer science) , ligation , chemistry , combinatorial chemistry , glycoside , computational biology , stereochemistry , computer science , biology , microbiology and biotechnology , mathematics , programming language , mathematical analysis
Major histocompatibility class II antigens have been bound to clustered glycosides for selective targeting of the dendritic cell mannose receptor. Di‐, tetra‐, and octavalent glycoside–antigen conjugates have been obtained after two, orthogonal, hydrazone/thioether ligations, performed by using thio derivatives of D ‐mannose, D ‐galactose, or D (−)‐quinic acid, glyoxylyl (or hydrazino)‐ N ‐chloroacetylated lysinyl trees, and N‐terminal hydrazino (or glyoxylyl) peptide antigens. Successful one‐pot condensations have been developed to account for the nature of the antigens and the valency of the trees.