The chemoenzymatic synthesis of the core trisaccharide of N-linked oligosaccharides using a recombinant β-mannosyltransferase

被引:30
作者
Watt, GM [1 ]
Revers, L [1 ]
Webberley, MC [1 ]
Wilson, IBH [1 ]
Flitsch, SL [1 ]
机构
[1] Univ Edinburgh, Dept Chem, Edinburgh Ctr Prot Technol, Edinburgh EH9 3JJ, Midlothian, Scotland
基金
英国生物技术与生命科学研究理事会;
关键词
N-linked oligosaccharides; beta-mannosyltransferase;
D O I
10.1016/S0008-6215(97)00261-9
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The chemical synthesis of the beta-mannosyl linkage of N-glycans has presented a great challenge to synthetic carbohydrate chemists. We have therefore investigated the application of beta-mannosyltransferases to the preparative synthesis N-linked core oligosaccharides. In this paper we report the chemoenzymatic synthesis of beta-D-mannopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->4)-2-acetamido-2-deoxy-alpha-D-glucopyranose on a preparative scale using a phytanyl-linked acceptor in the presence of a recombinant beta-(1-->4)-mannosyltransferase. (C) 1998 Elsevier Science Ltd.
引用
收藏
页码:533 / 541
页数:9
相关论文
共 37 条
[1]  
ALBRIGHT CF, 1990, J BIOL CHEM, V265, P7042
[2]   AMINO-SUGARS .123. THE SYNTHESIS OF O-BETA-D-MANNOPYRANOSYL-(1-]4)-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]4)-2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE .2. [J].
AUGE, C ;
WARREN, CD ;
JEANLOZ, RW ;
KISO, M ;
ANDERSON, L .
CARBOHYDRATE RESEARCH, 1980, 82 (01) :85-95
[3]   SYNTHESIS OF BETA-MANNOPYRANOSIDES BY INTRAMOLECULAR AGLYCON DELIVERY [J].
BARRESI, F ;
HINDSGAUL, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9376-9377
[4]  
BARRESI F, 1992, SYNLETT, P759
[5]   THE SYNTHESIS OF BETA-MANNOPYRANOSIDES BY INTRAMOLECULAR AGLYCON DELIVERY - SCOPE AND LIMITATIONS OF THE EXISTING METHODOLOGY [J].
BARRESI, F ;
HINDSGAUL, O .
CANADIAN JOURNAL OF CHEMISTRY, 1994, 72 (06) :1447-1465
[6]   LONG-RANGE INTRAMOLECULAR GLYCOSIDATION [J].
BOLS, M ;
HANSEN, HC .
CHEMISTRY LETTERS, 1994, (06) :1049-1052
[7]  
BOYD J, 1985, CARBOHYD RES, V139, P35
[8]   DETERMINATION OF THE STRUCTURES OF TRISACCHARIDES BY C-13-NMR SPECTROSCOPY [J].
BRADBURY, JH ;
JENKINS, GA .
CARBOHYDRATE RESEARCH, 1984, 126 (01) :125-156
[9]  
COUTO JR, 1984, J BIOL CHEM, V259, P378
[10]   Formation of beta-mannopyranosides of primary alcohols using the sulfoxide method [J].
Crich, D ;
Sun, SX .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4506-4507