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| N-(9-芴甲氧羰基)-O-(2,3,4,6-四苄基-α-D-半乳糖基)-L-丝氨酸的合成 |
| 李翔1,2,郭俊香1,张春梅1,吴秋业1,胡宏岗1* |
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(1. 第二军医大学药学院有机化学教研室,上海 200433;
2. 第二军医大学研究生管理大队,上海 200433
*通信作者) |
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| 摘要: |
| 目的 得到全苄基保护的糖氨基酸,用于各种糖肽的合成。 方法 以半乳糖为起始化合物通过5步反应得到全苄基保护的半乳糖硫苷(5),并将5与Fmoc-Ser-OAllyl进行糖基化,再脱去烯丙基得到目标糖氨基酸(1)。 结果 中间体及目标化合物结构均通过NMR、 MS等光谱确证,得到目标糖氨基酸。 结论 合成方法具有操作简便、通用性好及保护基易脱除等特点,目标糖氨基酸适用于各类糖肽的合成。 |
| 关键词: 糖氨基酸 丝氨酸 半乳糖 合成 |
| DOI：10.3724/SP.J.1008.2011.01227 |
| 投稿时间：2011-04-22修订日期：2011-07-26 |
| 基金项目:国家自然科学基金(20902109). |
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| Synthesis of N-(9-fluoren ylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-serine |
| LI Xiang1,2,GUO Jun-xiang1,ZHANG Chun-mei1,WU Qiu-ye1,HU Hong-gang1* |
(1. Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China;
2. Brigade of Postgraduate Administration, Second Military Medical University, Shanghai 200433, China
*Corresponding author.) |
| Abstract: |
| Objective To obtain fully protected glyco amino acid for synthesis of various glycopeptides. Methods With galactose as the initial compound, the full benzyl protected β-D-1-thio-galactopyranoside (5) was obtained after 5 steps of reactions. Then it was used as donor for glycosylation with Fmoc-Ser-OAlly to yield fully protected glyco amino acid. Finally, the allyl group was removed to obtain the objective glyco amino acid (1). Results The structures of the intermediate and objective compounds were confirmed by MS, 1HNMR and 13CNMR, and the target glyco amino acid was obtained. Conclusion The present synthetic method is simple to perform and can be widely used; meanwhile, the protective base can be easily removed. The target glyco amino acid is suitable for synthesis of various glycopeptides. |
| Key words: glyco amino acids serine galactose synthesis |
