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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (12): 1562-1566. 上一篇    下一篇

研究简报

Lewisx五糖的有效合成: 发展DC-靶向疫苗的有效分子

朱振元a,b，王靖雪c，吴玉章c，刘安军a，张勇民*,b,d   

  1. (a天津科技大学食品工程与生物技术学院 天津市食品营养与安全重点实验室 天津 300457)
    (b法国巴黎高等师范学院-CNRS-UMR 8642 巴黎 75231 法国)
    (c第三军医大学免疫学研究所 重庆 400038)
    (d浙江大学-巴黎高等师范学院药物化学联合实验室 浙江大学湖滨校区 杭州 310031)
  • 收稿日期:2006-06-19 修回日期:2006-12-21 发布日期:2007-12-04
  • 通讯作者: 张勇民

Efficient Synthesis of Lewisx Pentasaccharide: Useful Molecule to Develop a Potential DC-Targeting Strategy for Vaccina-tion

ZHU Zhen-Yuana,b, WANG Jing-Xuec, WU Yu-Zhangc
LIU An-Junb, ZHANG Yong-Min*,b,d   

  1. (a Tianjin Key Laboratory of Food Nutrition and Safety, College of Food Science and Biotechnol-ogy,
    Tianjin University of Science and Technology, Tianjin 300457, China)
    (b Ecole Normale Supérieure, Département de Chimie, CNRS-UMR 8642, Paris 75231, France)
    (c Institute of Immunology, The Third Military Medical University of People’s Liberation Army, Chongqing 400038, China)
    (c Zhejiang University-Ecole Normale Superieure Joint Laboratory of Medicinal Chemistry, Zhejiang University,
    Hubin Campus, Hangzhou 310031, China)
  • Received:2006-06-19 Revised:2006-12-21 Published:2007-12-04
  • Contact: ZHANG Yong-Min

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将选择性保护的乳糖二醇与Lewisx三糖在N-碘代丁二酰亚胺(NIS)/TfOH催化下高立体、高区域选择性糖苷化得Lewisx五糖, 后者脱保护后获得目标五糖, 总收率67.7%. 化合物结构经NMR, MS和元素分析确证.

关键词: Lewisx, 糖基化, 五糖

This paper describes an efficient synthesis of Lewisx pentasaccharide (1) based on a highly stereo- and regio-selective glycosylation. A lactoside diol was glycosylated with phenyl 6-O-benzyl-2-deoxy-2- phthalimido-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1-thio-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside (2) to give a pentasaccharide (4) which, after deprotection, afforded the target pentasaccharide.

Key words: glycosylation, pentasaccharide, Lewisx