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Automated Solid‐Phase Synthesis of Protected Tumor‐Associated Antigen and Blood Group Determinant Oligosaccharides
Author(s) -
Routenberg Love Kerry,
Seeberger Peter H.
Publication year - 2004
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.200352539
Subject(s) - glycosylation , linker , lewis acids and bases , chemistry , solid phase synthesis , protecting group , monosaccharide , combinatorial chemistry , stereochemistry , computer science , computational biology , biochemistry , catalysis , organic chemistry , biology , programming language , peptide , alkyl
Speedy synthesis : The development of a novel linker and monitoring each glycosylation reaction during automated solid‐phase synthesis allows the rapid assembly of three Lewis‐type cell‐surface oligosaccharides. The synthesis of the protected tumor‐marker Le y –Le x (see structure; Bn=benzyl, Piv=pivaloyl, TCA=trichloroacetyl) from monosaccharide building blocks was achieved in just 23 h, while the syntheses of Lewis X and Lewis Y required only 12 and 14 h, respectively.