标题:Synthesis of a trisaccharide repeating unit of the O-antigen from Burkholderia cenocepacia and its dimer
作者:Bi, Ningning; Xiong, Chenghe; Jin, Guoxia; Guo, Zhongwu; Gu, Guofeng
作者机构:[Bi, Ningning; Xiong, Chenghe; Guo, Zhongwu; Gu, Guofeng] Shandong Univ, Shandong Prov Key Lab Carbohydrate Chem & Glycobi, Natl Glycoengn Res Ctr, 27 更多
通讯作者:Gu, Guofeng
通讯作者地址:[Guo, ZW; Gu, GF]Shandong Univ, Shandong Prov Key Lab Carbohydrate Chem & Glycobi, Natl Glycoengn Res Ctr, 27 Shanda Nan Lu, Jinan 250010, Shandong, P 更多
来源:CARBOHYDRATE RESEARCH
出版年:2017
卷:451
页码:1-11
DOI:10.1016/j.carres.2017.09.001
关键词:Burkholderia cenocepacia; Lipopolysaccharide; O-antigen; Repeating unit;; Synthesis
摘要:The trisaccharide repeating unit of an O-antigen derived from Burkholderia cenocepacia and its dimer, i. e., alpha-L-Rhap-(1 -> 3)-alpha-D-GalpNAc-(1 -> 3)-beta-D-GalpNAc-O(CH2)(3)N-3 (1) and alpha-L-Rhap-(1 -> 3)-alpha-D-GalpNAc-( 1 -> 3)-beta-D-GalpNAc-(1 /4)-alpha-L-Rhap-(1 -> 3)-alpha-D-GalpNAc-(1 -> 3)-beta-D-GalpNAc-O(CH2)(3)N-3 (2), respectively, were synthesized via a highly convergent strategy. Glycosylation of galactosaminyl acceptor 4 with galactosaminyl trichloroacetimidate donor 5 was followed by condensation of resulting disaccharide acceptor 12 with rhamnosyl imidate donor 6 to furnish stereoselectively trisaccharyl thioglycoside 3, which was used as a key and common glycosyl donor for the construction of both 1 and 2. Title molecule 1 was prepared by glycosylation of 3-azidopropanol with 3 and subsequently global deprotection, whereas coupling reaction of 3 with a trisaccharide acceptor 21 containing an 2,3-O-position acetonide-modified rhamnose residue, followed by global deprotection, generated the dimer 2 in a convergent [3 + 3] manner. (C) 2017 Elsevier Ltd. All rights reserved.
收录类别:EI;SCOPUS;SCIE
WOS核心被引频次:1
Scopus被引频次:1
资源类型:期刊论文
原文链接:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85029393795&doi=10.1016%2fj.carres.2017.09.001&partnerID=40&md5=985c52e9315c23c0d191747f9b984d05
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