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Chemical synthesis of homogeneous glycopeptides and glycoproteins
Author(s) -
Kajihara Yasuhiro,
Yamamoto Naoki,
Okamoto Ryo,
Hirano Kiriko,
Murase Takefumi
Publication year - 2010
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.200900024
Subject(s) - glycopeptide , glycoprotein , oligosaccharide , homogeneous , native chemical ligation , chemistry , biochemistry , chemical synthesis , combinatorial chemistry , computational biology , biology , in vitro , mathematics , combinatorics , antibiotics
Oligosaccharides linked to proteins are known to play important roles in several biological events. However, oligosaccharides are heterogeneous, which has hindered detailed elucidation of oligosaccharide functions. In order to solve this problem, glycoproteins having homogeneous oligosaccharides have long been required. For this purpose, an efficient preparative method of complex‐type oligosaccharides has been investigated from a natural source and this method was found to afford over 24 kinds of diverse complex‐type oligosaccharides by use of chemical methods and branch‐specific sequential glycosidase digestion. The sufficient amount of homogeneous complex type oligosaccharides obtained enabled us to examine the synthesis of homogeneous glycopeptides as well as glycoproteins by use of solid phase glycopeptide synthetic method and native chemical ligation. This review describes recent progress related to the efficient method of oligosaccharide preparation and synthesis of glycoproteins including bioactive erythropoietin. © 2010 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 10: 80–100; 2010: Published online in Wiley InterScience ( www.interscience.wiley.com ) DOI 10.1002/tcr.200900024