Synthesis of selected aminodeoxy analogues of galabiose and globotriose

被引:14
作者
Hansen, HC [1 ]
Magnusson, G [1 ]
机构
[1] Lund Univ, Ctr Chem & Chem Engn, S-22100 Lund, Sweden
基金
美国国家卫生研究院;
关键词
galabiose analogues; globotriose analogues; aminodeoxy; bacterial binding inhibitors;
D O I
10.1016/S0008-6215(99)00229-3
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
Six aminodeoxy 2-(trimethylsilyl)ethyl (Me3SiEt) glycoside analogues of galabiose (4'- and 6'-aminodeoxy) and globotriose (6 "-, 4 "-, 2 "-, and 6'-aminodeoxy) were synthesized by glycosylation of protected Me3SiEt galactoside and lactoside accepters with azido-substituted monosaccharide donors, followed by reduction of the azido groups and removal of the protecting groups. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:166 / 180
页数:15
相关论文
共 41 条
[1]   MOLECULAR MECHANICS - THE MM3 FORCE-FIELD FOR HYDROCARBONS .1. [J].
ALLINGER, NL ;
YUH, YH ;
LII, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8551-8566
[2]   A MOLECULAR MECHANICS FORCE-FIELD (MM3) FOR ALCOHOLS AND ETHERS [J].
ALLINGER, NL ;
RAHMAN, M ;
LII, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8293-8307
[3]  
BINKLEY RW, 1988, MODERN CARBOHYDRATE, P178
[4]   SYNTHETIC RECEPTOR ANALOGS - THE CONFORMATION OF METHYL 4-O-ALPHA-D-GALACTOPYRANOSYL-BETA-D-GALACTOPYRANOSIDE (METHYL-BETA-D-GALABIOSIDE) AND RELATED DERIVATIVES, DETERMINED BY NMR AND COMPUTATIONAL METHODS .2. [J].
BOCK, K ;
FREJD, T ;
KIHLBERG, J ;
MAGNUSSON, G .
CARBOHYDRATE RESEARCH, 1988, 176 (02) :253-270
[5]   LIPID MODULATION OF GLYCOLIPID RECEPTOR FUNCTION - AVAILABILITY OF GAL(ALPHA-1-4)GAL DISACCHARIDE FOR VEROTOXIN BINDING IN NATURAL AND SYNTHETIC GLYCOLIPIDS [J].
BOYD, B ;
MAGNUSSON, G ;
ZHANG, ZY ;
LINGWOOD, CA .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1994, 223 (03) :873-878
[6]   SYNTHESIS OF SPACER-ARM, LIPID, AND ETHYL GLYCOSIDES OF THE TRISACCHARIDE PORTION [ALPHA-D-GAL-(1-]4)-BETA-D-GAL-(1-]4)-BETA-D-GLC] OF THE BLOOD-GROUP PK ANTIGEN - PREPARATION OF NEOGLYCOPROTEINS [J].
DAHMEN, J ;
FREJD, T ;
MAGNUSSON, G ;
NOORI, G ;
CARLSTROM, AS .
CARBOHYDRATE RESEARCH, 1984, 127 (01) :15-25
[7]   Synthesis of lactam and acetamido analogues of sialyl Lewis x tetrasaccharide and Lewis x trisaccharide [J].
Ellervik, U ;
Grundberg, H ;
Magnusson, G .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9323-9338
[8]   SYNTHESIS OF PARA-TRIFLUOROACETAMIDOPHENYL O-ALPHA-D-GALACTOPYRANOSYL-(1-]2)-O-ALPHA-D-MANNOPYRANOSYL-(1-]4)-ALPHA-L-RHAMNOPYRANOSIDE [J].
GAREGG, PJ ;
HULTBERG, H ;
LINDBERG, C .
CARBOHYDRATE RESEARCH, 1980, 83 (01) :157-162
[9]   NUCLEAR-MAGNETIC-RESONANCE AND CONFORMATIONAL INVESTIGATIONS OF THE PENTASACCHARIDE OF THE FORSSMAN ANTIGEN AND OVERLAPPING DISACCHARIDE, TRISACCHARIDE, AND TETRASACCHARIDE SEQUENCES [J].
GRONBERG, G ;
NILSSON, U ;
BOCK, K ;
MAGNUSSON, G .
CARBOHYDRATE RESEARCH, 1994, 257 (01) :35-54
[10]  
HAATAJA S, 1994, J BIOL CHEM, V269, P27466