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Total Synthesis of the Glycopeptide Recognition Domain of the P‐Selectin Glycoprotein Ligand 1
Author(s) -
Baumann Katharina,
Kowalczyk Danuta,
Kunz Horst
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200705762
Subject(s) - glycopeptide , chemistry , threonine , glycosylation , glycoprotein , ligand (biochemistry) , selectin , conjugate , block (permutation group theory) , biochemistry , antigen , solid phase synthesis , stereochemistry , phosphorylation , biology , peptide , receptor , immunology , organic chemistry , adhesion , mathematical analysis , mathematics , serine , geometry , antibiotics
Block glycosylation of a T antigen–threonine conjugate with a sialyl Lewis x trichloroacetimidate was used to synthesize a sialyl Lewis x –T antigen–threonine building block. Selective protecting‐group manipulations furnished a compound with exclusively acetyl‐protected functions in the carbohydrate portion; this intermediate is sufficiently acid‐stable that it is applicable to the solid‐phase synthesis of binding site A of the P‐selectin ligand PSGL‐1.