Facile synthesis of a pentasaccharide repeating unit corresponding to the common O-antigen of Salmonella enterica O57 and Escherichia coli O51

被引:7
作者
Ghosh, Tamashree [1 ]
Santra, Abhishek [1 ]
Misra, Anup Kumar [1 ]
机构
[1] Bose Inst, Div Mol Med, Kolkata 700054, India
关键词
PROMOTED REACTIONS; DERIVATIVES; ETHER;
D O I
10.1016/j.tetasy.2013.04.001
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A concise chemical synthetic strategy has been developed for the synthesis of a pentasaccharide present in the O-antigen of Salmonella enterica O57 and Escherichia coli O51 strains. A sequential glycosylation strategy has been adopted for the synthesis of the target pentasaccharide. All intermediate steps are high yielding and the glycosylation steps are stereoselective. A number of recently developed methodologies have been used in the synthesis. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:606 / 611
页数:6
相关论文
共 31 条
[1]   BENZOYL CYANIDE AS A SELECTIVE ACYLATING AGENT [J].
ABBAS, SA ;
HAINES, AH .
CARBOHYDRATE RESEARCH, 1975, 39 (02) :358-363
[2]  
BERN C, 1992, B WORLD HEALTH ORGAN, V70, P705
[3]   The p-methoxybenzyl ether as an in situ-removable carbohydrate-protecting group:: a simple one-pot synthesis of the globotetraose tetrasaccharide [J].
Bhattacharyya, S ;
Magnusson, BG ;
Wellmar, U ;
Nilsson, UJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, Royal Society of Chemistry (08) :886-890
[4]  
BIYCE J, 2005, LANCET, V365, P1147
[5]  
BOCK K, 1975, ACTA CHEM SCAND B, VB 29, P258, DOI 10.3891/acta.chem.scand.29b-0181
[6]   Bacterial contamination of animal feed and its relationship to human foodborne illness [J].
Crump, JA ;
Griffin, PM ;
Angulo, FJ .
CLINICAL INFECTIOUS DISEASES, 2002, 35 (07) :859-865
[7]   The effector repertoire of enteropathogenic E-coli: ganging up on the host cell [J].
Dean, Paul ;
Kenny, Brendan .
CURRENT OPINION IN MICROBIOLOGY, 2009, 12 (01) :101-109
[8]   Armed-Disarmed Effects in Carbohydrate Chemistry: History, Synthetic and Mechanistic Studies [J].
Fraser-Reid, Bert ;
Cristobal Lopez, J. .
REACTIVITY TUNING IN OLIGOSACCHARIDE ASSEMBLY, 2011, 301 :1-29
[9]   Synthesis of the hexasaccharide repeating unit corresponding to the cell wall lipopolysaccharide of Azospirillum irakense KBC1 [J].
Ghosh, Samir ;
Misra, Anup Kumar .
TETRAHEDRON-ASYMMETRY, 2010, 21 (23) :2755-2761
[10]   Rapid screening of Salmonella enterica serovars Enteritidis, Hadar, Heidelberg and Typhimurium using a serologically-correlative allelotyping PCR targeting the O and H antigen alleles [J].
Hong, Yang ;
Liu, Tongrui ;
Lee, Margie D. ;
Hofacre, Charles L. ;
Maier, Marie ;
White, David G. ;
Ayers, Sherry ;
Wang, Lihua ;
Berghaus, Roy ;
Maurer, John J. .
BMC MICROBIOLOGY, 2008, 8 (1)