SYNTHESIS OF 2-(PARA-TRIFLUOROACETAMIDOPHENYL)ETHYL AND METHYL GLYCOSIDES OF O-(2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSYL)-(1-]3)-O-ALPHA-L-RHAMNOPYRANOSYL-(1-]3)-O-ALPHA-L-RHAMNOPYRANOSYL-(1-]2)-ALPHA-D-GALACTOPYRANOSE, CORRESPONDING TO THE REPEATING UNIT OF THE SHIGELLA-DYSENTERIAE TYPE-1 CELL-WALL LIPOPOLYSACCHARIDE, AND ALSO OF DISACCHARIDE AND TRISACCHARIDE FRAGMENTS THEREOF

被引:6
作者
GAREGG, PJ
HALLGREN, C
机构
[1] Department of Organic Chemistry, Arrhenius Laboratory Stockholm University
关键词
D O I
10.1080/07328309208017805
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
2-(p-Trifluoroacetamidophenyl)ethyl and methyl glycosides of a tetrasaccharide repeating unit corresponding to that of the Shigella dysenteriae type 1 cell wall lipopolysaccharide, of a rhamnosyl-rhamnosylgalactose trisaccharide, and of a rhamnosylrhamnose and a rhamnosylgalactose disaccharides are described. The main glycosylation method used was activation of thioglycosides with dimethyl(methylthio)-sulfonium triflate (DMTST).
引用
收藏
页码:445 / 461
页数:17
相关论文
共 11 条
[1]   INCIDENCE AND AVOIDANCE OF STEREOSPECIFIC 1,2-ETHYLTHIO GROUP MIGRATION DURING THE SYNTHESIS OF ETHYL 1-THIO-ALPHA-L-RHAMNOPYRANOSIDE 2,3-ORTHOESTER [J].
AUZANNEAU, FI ;
BUNDLE, DR .
CARBOHYDRATE RESEARCH, 1991, 212 :13-24
[2]   THE BEHAVIOUR OF DERIVATIVES OF 3-4-ANHYDROGALACTOSE TOWARDS ACIDIC REAGENTS .1. [J].
BUCHANAN, JG .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (MAR) :995-1000
[3]  
CLASSON B, 1988, 14TH INT CARB S STOC
[4]   SOMATIC ANTIGENS OF SHIGELLA - STRUCTURAL INVESTIGATION ON O-SPECIFIC POLYSACCHARIDE CHAIN OF SHIGELLA-DYSENTERIAE TYPE-1 LIPOPOLYSACCHARIDE [J].
DMITRIEV, BA ;
KNIREL, YA ;
KOCHETKOV, NK ;
HOFMAN, IL .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1976, 66 (03) :559-566
[5]  
Fischer E., 1920, BER, V53, P2362
[6]   A NOVEL PROMOTER FOR THE EFFICIENT CONSTRUCTION OF 1,2-TRANS LINKAGES IN GLYCOSIDE SYNTHESIS, USING THIOGLYCOSIDES AS GLYCOSYL DONORS [J].
FUGEDI, P ;
GAREGG, PJ .
CARBOHYDRATE RESEARCH, 1986, 149 (01) :C9-C12
[7]   CHEMISTRY OF GLYCOSIDIC LINKAGE - EFFICIENT SYNTHESIS OF 1,2-TRANS-DISACCHARIDES [J].
HANESSIAN, S ;
BANOUB, J .
CARBOHYDRATE RESEARCH, 1977, 53 (01) :C13-C16
[8]   BUILDING-BLOCKS OF OLIGOSACCHARIDES .7. SYNTHESIS OF SELECTIVELY BLOCKED 2-AZIDO-2-DEOXY-D-GLUCOPYRANOSYL HALIDES AND D-GALACTOPYRANOSYL HALIDES - REACTIVITY AND C-13-NMR SPECTRA [J].
PAULSEN, H ;
RICHTER, A ;
SINNWELL, V ;
STENZEL, W .
CARBOHYDRATE RESEARCH, 1978, 64 (JUL) :339-362
[9]   SYNTHESIS OF A DI-SACCHARIDE AND A TRI-SACCHARIDE RELATED TO THE K-ANTIGEN OF KLEBSIELLA TYPE-10 AND A STUDY OF THEIR INHIBITION IN THE PRECIPITIN REACTION [J].
SARKAR, AK ;
RAY, AK ;
ROY, N .
CARBOHYDRATE RESEARCH, 1989, 190 (02) :181-189
[10]  
VANSTEIJN AMP, 1989, RECL TRAV CHIM PAY B, V108, P374