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Synthesis of N ‐Glycopeptide Clusters with Lewis x Antigen Side Chains and Their Coupling to Carrier Proteins
Author(s) -
von dem Bruch Karsten,
Kunz Horst
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199401011
Subject(s) - glycopeptide , trisaccharide , chemistry , antigen , keyhole limpet hemocyanin , glycoprotein , hemocyanin , biochemistry , immunology , biology , antibiotics
As a tumor‐associated cell‐antigen mimic , Lewis x trisaccharide determinant 1 was constructed with the azide function as anomeric protecting group with the aid of a 4‐Mpm‐protected (Mpm = methoxyphenylmethyl) fucosyl donor. Exchange of the OMpm functions for OAc groups furnishes a Lewis x trisaccharide stable enough against acid attack for glycopeptide synthesis. A glycopeptide with two Lewis x antigen side chains was deblocked and coupled to bovine serum albumin as well as to KLH (keyhole limpet hemocyanin). These synthetic glycoproteins simulate biantennary Lewis x antigen structures.