一种光氟代糖基供体的合成与应用
Synthesis and applications of a light-fluorous glycosyl donor.
作者信息
Zhang Fa, Zhang Wei, Zhang Yan, Curran Dennis P, Liu Gang
机构信息
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, PR China.
出版信息
J Org Chem. 2009 Mar 20;74(6):2594-7. doi: 10.1021/jo9000993.
Abstract
A new method using a light-fluorous glycosyl donor and an orthogonal tagging strategy to synthesize oligosaccharides and glycoconjugates has been developed. The glycosyl donor orthogonally protected with a C8F17-silyl tag and benzoyl groups was reacted with excess amounts of glycosyl acceptor. Fluorous solid-phase extraction separated the glycosylated product and unreacted glycosyl acceptor. This new protocol has high reaction efficiency and easy separation, which was demonstrated in the synthesis of an unprotected trisaccharide and an O-glycosylated serine in this paper.
摘要
一种使用光氟糖基供体和正交标记策略合成寡糖和糖缀合物的新方法已被开发出来。用C8F17-硅烷基标签和苯甲酰基正交保护的糖基供体与过量的糖基受体反应。氟固相萃取分离出糖基化产物和未反应的糖基受体。本文通过合成一种未保护的三糖和一个O-糖基化丝氨酸证明了该新方案具有高反应效率和易于分离的特点。
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本文引用的文献
1
4-Acetoxy-2,2-dimethylbutanoate: a useful carbohydrate protecting group for the selective formation of β-(1→3)-d-glucans.4-乙酰氧基-2,2-二甲基丁酸酯：一种用于选择性形成β-(1→3)-D-葡聚糖的有用碳水化合物保护基团。
Tetrahedron Lett. 2005 May;46(19):3417-3421. doi: 10.1016/j.tetlet.2005.03.099.
2
Mono- Vs. Di-flourous tagged Glucosamines for Iterative Oligosaccharide Synthesis.用于迭代寡糖合成的单氟与二氟标记葡糖胺
J Fluor Chem. 2008 Oct;129(10):978-982. doi: 10.1016/j.jfluchem.2008.05.001.
3
New chemical and biological applications of fluorous technologies.氟技术的新化学和生物学应用。
Chem Commun (Camb). 2008 Nov 30(44):5686-94. doi: 10.1039/b812433g. Epub 2008 Oct 14.
4
Protecting-group-based colorimetric monitoring of fluorous-phase and solid-phase synthesis of oligoglucosamines.基于保护基的糖缀合物的氟相和固相合成的比色监测。
Org Lett. 2008 Dec 4;10(23):5381-4. doi: 10.1021/ol802229b.
5
Chemistry. Fluorous tags unstick messy chemical biology problems.化学。氟代标签解决了复杂的化学生物学问题。
Science. 2008 Sep 19;321(5896):1645-6. doi: 10.1126/science.1158721.
6
Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers.迈向溶液相自动迭代合成：氟代标签辅助的线性和支链甘露糖低聚物的溶液相合成
Org Biomol Chem. 2008 Aug 7;6(15):2686-91. doi: 10.1039/b803451f. Epub 2008 May 16.
7
Synthetic applications of fluorous solid-phase extraction (F-SPE).氟相固相萃取（F-SPE）的合成应用。
Tetrahedron. 2006 Dec 18;62(51):11837-11865. doi: 10.1016/j.tet.2006.08.051.
8
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Org Lett. 2008 Mar 6;10(5):785-8. doi: 10.1021/ol702915e. Epub 2008 Feb 5.
9
Synthesis and quantitative evaluation of Glycero-D-manno-heptose binding to concanavalin A by fluorous-tag assistance.通过氟标签辅助合成并定量评估甘油-D-甘露庚糖与伴刀豆球蛋白A的结合。
Angew Chem Int Ed Engl. 2008;47(9):1707-10. doi: 10.1002/anie.200704262.
10
Automated oligosaccharide synthesis.自动化寡糖合成
Chem Soc Rev. 2008 Jan;37(1):19-28. doi: 10.1039/b511197h. Epub 2007 Aug 20.
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