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Selective deprotection of the Cbz amine protecting group for the facile synthesis of kanamycin A dimers linked at N-3 ′′ position
Chen, Gui-Hui; Pan, Pan; Chen, Ying; Meng, Xiang-Bao; Li, Zhong-Jun
关键词Regioselective Aminoglycoside Kanamycin A Dimer
刊名TETRAHEDRON
2009-08-01
DOI10.1016/j.tet.2009.06.002
65期:31页:5922-5927
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]RNA-BINDING ; AMINOGLYCOSIDE ANTIBIOTICS ; RESISTANCE ; DESIGN
英文摘要

The optimal conditions for the regioselective deprotection of per-N-Cbz-kanamycin A and the reaction mechanism was investigated. We found that the Cbz group at N-3 ′′ position was selectively deprotected under milder basic conditions and the cyclic carbamate is an intermediate of the deprotection reaction. The selective deprotection of the amine protecting group enable us to synthesize several kanamycin A dimers linked at N-3 ′′ position in a straightforward way. (C) 2009 Elsevier Ltd. All rights reserved.

语种英语
WOS记录号WOS:000268217000007
项目编号2004CB518904
资助机构National Basic Research Program (973 Program)
引用统计
被引频次:10[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/58883
专题北京大学药学院
北京大学药学院_化学生物学系
作者单位Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Chen, Gui-Hui,Pan, Pan,Chen, Ying,et al. Selective deprotection of the Cbz amine protecting group for the facile synthesis of kanamycin A dimers linked at N-3 ′′ position[J]. TETRAHEDRON,2009,65(31):5922-5927.
APA Chen, Gui-Hui,Pan, Pan,Chen, Ying,Meng, Xiang-Bao,&Li, Zhong-Jun.(2009).Selective deprotection of the Cbz amine protecting group for the facile synthesis of kanamycin A dimers linked at N-3 ′′ position.TETRAHEDRON,65(31),5922-5927.
MLA Chen, Gui-Hui,et al."Selective deprotection of the Cbz amine protecting group for the facile synthesis of kanamycin A dimers linked at N-3 ′′ position".TETRAHEDRON 65.31(2009):5922-5927.
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