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Synthesis of Multiantennary Complex Type N ‐Glycans by Use of Modular Building Blocks
Author(s) -
Unverzagt Carlo,
Gundel Gislinde,
Eller Steffen,
Schuberth Ralf,
Seifert Joachim,
Weiss Harald,
Niemietz Mathäus,
Pischl Matthias,
Raps Claudia
Publication year - 2009
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/chem.200901908
Subject(s) - chitobiose , moiety , glycan , modular design , trisaccharide , chemistry , stereochemistry , stereoselectivity , sequence (biology) , combinatorial chemistry , glycoprotein , computer science , biochemistry , programming language , chitin , chitosan , catalysis
A modular set of oligosaccharide building blocks was developed for the synthesis of multiantennary N ‐glycans of the complex type, which are commonly found on glycoproteins. The donor building blocks were laid out for the elongation of a core trisaccharide acceptor (β‐mannosyl chitobiose) conveniently protected with a single benzylidene moiety at the β‐mannoside. Through two consecutive regio‐ and stereoselective couplings the donors gave N ‐glycans with three to five antennae in high yields. Due to the consistent protection group pattern of the donors the deprotection of the final products can be performed by using a general reaction sequence.