Synthesis of Glycans and Glycopolymers Through Engineered Enzymes

被引:41
作者
Armstrong, Zachary [1 ]
Withers, Stephen G. [1 ,2 ]
机构
[1] Univ British Columbia, Genome Sci & Technol Program, Vancouver, BC V5Z 1M9, Canada
[2] Univ British Columbia, Ctr High Throughput Biol, Dept Chem, Vancouver, BC V5Z 1M9, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
polysaccharides; enzymatic synthesis; engineered enzymes; engineered polymers; glycopolymers; BETA-N-ACETYLGLUCOSAMINIDASE; SUBSTRATE-ASSISTED CATALYSIS; CHEMOENZYMATIC SYNTHESIS; DIRECTED EVOLUTION; OLIGOSACCHARIDE SYNTHESIS; GLYCOSPHINGOLIPID SYNTHESIS; GLYCOSYNTHASE ACTIVITY; MUTANT GLYCOSIDASES; EFFICIENT SYNTHESIS; ENZYMATIC-SYNTHESIS;
D O I
10.1002/bip.22335
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
070307 [化学生物学]; 071010 [生物化学与分子生物学];
摘要
The synthesis of defined glycans enables us to further understand their roles in a biological context. Although useful chemical methods have been developed for the synthesis of glycans, these typically require complex protection and deprotection steps along with challenging control of anomeric stereochemistry. Enzymatic methods offer an attractive alternative to chemical synthesis. In particular, the use of glycosynthases and thioglycoligases, classes of engineered glycoside hydrolases, offers an enticing approach to the stereo- and regioselective synthesis of glycans without the need for protecting groups. Herein, we describe recent progress in the use of glycosynthases and thioglycoligases for the synthesis of glycans and glycopolymers. (C) 2013 Wiley Periodicals, Inc.
引用
收藏
页码:666 / 674
页数:9
相关论文
共 77 条
[1]
Exploring the synthetic potency of the first furanothioglycoligase through original remote activation [J].
Almendros, Melanie ;
Danalev, Dantcho ;
Francois-Heude, Marc ;
Loyer, Pascal ;
Legentil, Laurent ;
Nugier-Chauvin, Caroline ;
Daniellou, Richard ;
Ferrieres, Vincent .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (24) :8371-8378
[2]
Convergent Synthesis of Homogeneous Glc1Man9GlcNAc2-Protein and Derivatives as Ligands of Molecular Chaperones in Protein Quality Control [J].
Amin, Mohammed N. ;
Huang, Wei ;
Mizanur, Rahman M. ;
Wang, Lai-Xi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (36) :14404-14417
[3]
Enzymatic Thioxyloside Synthesis: Characterization of Thioglycoligase Variants Identified from A Site-Saturation Mutagenesis Library of Bacillus Circulans Xylanase [J].
Armstrong, Zachary ;
Reitinger, Stephan ;
Kantner, Terrence ;
Withers, Stephen G. .
CHEMBIOCHEM, 2010, 11 (04) :533-538
[4]
Glycosynthase activity of Geobacillus stearothermophilus GH52 β-xylosidase:: Efficient synthesis of xylooligosaccharides from α-D-xylopyranosyl fluoride through a conjugated reaction [J].
Ben-David, Alon ;
Bravman, Tsafrir ;
Balazs, Yael S. ;
Czjzek, Mirjam ;
Schomburg, Dietmar ;
Shoham, Gil ;
Shoham, Yuval .
CHEMBIOCHEM, 2007, 8 (17) :2145-2151
[5]
PROTEIN DATA BANK - COMPUTER-BASED ARCHIVAL FILE FOR MACROMOLECULAR STRUCTURES [J].
BERNSTEIN, FC ;
KOETZLE, TF ;
WILLIAMS, GJB ;
MEYER, EF ;
BRICE, MD ;
RODGERS, JR ;
KENNARD, O ;
SHIMANOUCHI, T ;
TASUMI, M .
JOURNAL OF MOLECULAR BIOLOGY, 1977, 112 (03) :535-542
[6]
Structural analysis of the α-2,3-sialyltransferase cst-i from Campylobacter jejuni in apo and substrate-analogue bound forms [J].
Chiu, Cecilia P. C. ;
Lairson, Luke L. ;
Gilbert, Michel ;
Wakarchuk, Warren W. ;
Withers, Stephen G. ;
Strynadka, Natalie C. J. .
BIOCHEMISTRY, 2007, 46 (24) :7196-7204
[7]
Glycosynthases as tools for the production of glycan analogs of natural products [J].
Cobucci-Ponzano, Beatrice ;
Moracci, Marco .
NATURAL PRODUCT REPORTS, 2012, 29 (06) :697-709
[8]
An evolving hierarchical family classification for glycosyltransferases [J].
Coutinho, PM ;
Deleury, E ;
Davies, GJ ;
Henrissat, B .
JOURNAL OF MOLECULAR BIOLOGY, 2003, 328 (02) :307-317
[9]
Daniel E. L., 2005, ORGANIC CHEM SUGARS
[10]
Rapid chemoenzymatic synthesis of monodisperse hyaluronan oligosaccharides with immobilized enzyme reactors [J].
Deangelis, PL ;
Oatman, LC ;
Gay, DF .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (37) :35199-35203