| 保护的几丁寡糖及结构类似物的合成：复杂氨基寡糖合成的通用方法 |
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| 引用本文： | 朱振元a,b 张勇民b,c 孙超b 姚艳萍b.保护的几丁寡糖及结构类似物的合成：复杂氨基寡糖合成的通用方法[J].中国化学,2008,26(8):1519-1522. |
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| 作者姓名： | 朱振元a b 张勇民b c 孙超b 姚艳萍b |
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| 作者单位： | （天津科技大学食品工程与生物技术学院 天津 300457） ;（法国巴黎高等师范学院-CNRS-umr8642，24 rue Lhomond, 75231 Paris, France) ;（浙江大学-巴黎高师药物化学联合实验室浙江大学湖滨校区 杭州 310031） ; |
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| 摘 要： | 建立了逐步合成具有重要生物活性的2-脱氧-2-氨基葡萄糖寡糖链的通用方法。采用邻苯二甲酰基保护氨基、硫代苯基为还原末端的离去基团，以氨基葡萄糖为起始原料，几种保护的几丁寡糖及结构类似物被合成：3-O-乙酰基-4，6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚氨基-b-D-吡喃葡萄糖-（1→4）-（3-O-乙酰基-6-O-苄基-2-脱氧-2-邻苯二甲酰亚氨基）-b-D-吡喃葡萄糖甲苷（4）、3-O-乙酰基-4，6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚氨基-b-D-吡喃葡萄糖-（1→4）-（3-O-乙酰基-6-O-苄基-2-脱氧-2-邻苯二甲酰亚氨基-b-D-吡喃葡萄糖）-（1→4）-（3-O-乙酰基-6-O-苄基-2-脱氧-2-邻苯二甲酰亚氨基）-b-D-吡喃葡萄糖甲苷（6）、3-O-乙酰基-4，6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚氨基-b-D-吡喃葡萄糖-（1→3）-（4，6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚氨基）-b-D-吡喃葡萄糖甲苷（8）、3-O-乙酰基-4，6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚氨基-b-D-吡喃葡萄糖-（1→3）-（4，6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚氨基-b-D-吡喃葡萄糖）- （1→3）-（4，6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚氨基）- b-D-吡喃葡萄糖甲苷（10）。所合成化合物通过核磁共振和质谱分析确证了其化学结构。
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| 关 键 词： | 氨基葡萄糖、糖基化、几丁寡糖 |
| 收稿时间： | 2007-5-15 |
| 修稿时间： | 2007-12-21 |
Synthesis of Protected N‐Acetylchitooligosaccharide and Its Analogues: A Versatile Approach for the Synthesis of Complex Oligosaccharides of 2‐Amino‐2‐deoxy Sugar |
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| Zhen‐Yuan ZHU,Yong‐Min ZHANG,Chao SUN,Yan‐Ping YAO.Synthesis of Protected N‐Acetylchitooligosaccharide and Its Analogues: A Versatile Approach for the Synthesis of Complex Oligosaccharides of 2‐Amino‐2‐deoxy Sugar[J].Chinese Journal of Chemistry,2008,26(8):1519-1522. |
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| Authors: | Zhen‐Yuan ZHU Yong‐Min ZHANG Chao SUN Yan‐Ping YAO |
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| Institution: | 1. Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Science and Biotechnology, Tianjin University of Science and Technology, Tianjin 300457, China;2. Ecole Normale Suprieure, Dpartement de Chimie, CNRS‐UMR 8642, 24 rue Lhomond, 75231 Paris Cedex 05, France;3. Zhejiang University‐ Ecole Normale Suprieure Joint Laboratory of Medicinal Chemistry, Zhejiang University, Hubin Campus, Hangzhou, Zhejiang 310031, China |
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| Abstract: | A stepwise synthesis of oligosaccharide chains containing 2‐amino‐2‐deoxy‐D‐glucopyranose units was elaborated as a new versatile approach for preparation of biologically important oligosaccharides having 2‐amino‐ 2‐deoxysugars. Utilizing N‐phthalic acyl group as the protective group of amine, and phenylthiolate as the leaving group at the reducing terminal, protected N‐acetylchitooligosaccharide and its analogues, methyl (3‐O‐acetyl‐4,6‐O‐ benzylene‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranosyl)‐(1→4)‐3‐O‐acetyl‐6‐O‐benzyl‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranoside 4 , methyl (3‐O‐acetyl‐4,6‐O‐benzylene‐2‐deoxy‐2‐phthalimido‐β‐D‐gluco‐pyranosyl)‐(1→4)‐ (3‐O‐acetyl‐6‐O‐benzyl‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranosyl)‐(1→4)‐3‐O‐acetyl‐6‐O‐benzyl‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranoside 6 , methyl (3‐O‐acetyl‐4,6‐O‐benzylene‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranosyl)‐(1→3)‐4,6‐O‐benzylene‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranoside 8 , and methyl (3‐O‐acetyl‐4,6‐O‐benzylene‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranosyl)‐(1→3)‐(4,6‐O‐benzylene‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranosyl)‐(1→3)‐4,6‐O‐benzylene‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranoside 10 , were designed and synthesized by amino glucose as the starting material, which were all characterized by 1H NMR, 13C NMR and HRMS. |
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| Keywords: | 2‐amino‐2‐deoxy‐glucose glycosylation N‐acetylchitooligosaccharide |
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