Total Synthesis of the Glycopeptide Recognition Domain of the P‐Selectin Glycoprotein Ligand 1 | Zendy

Baumann Katharina | Zendy; Kowalczyk Danuta | Zendy; Kunz Horst | Zendy

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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.

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