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Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations
Pang, Li-Juan1; Wang, Dan1; Zhou, Jian1; Zhang, Li-He1; Ye, Xin-Shan1
刊名ORGANIC & BIOMOLECULAR CHEMISTRY
2009
DOI10.1039/b907518f
7期:20页:4252-4266
收录类别SCI ; IC
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]SURFACE-PLASMON RESONANCE ; RNA HAIRPIN LOOPS ; AMINOGLYCOSIDE ANTIBIOTICS ; RIBOSOMAL-RNA ; TARGETING RNA ; A-SITE ; RESISTANCE ; DESIGN ; MIMETICS ; 2-DEOXYSTREPTAMINE
英文摘要

Neamine is normally found as a core structure of aminoglycoside antibiotics. In order to understand the relationship between the antibiotic activity and the configurations of the functional groups of neamine, a series of novel neamine analogues with functional group manipulations on the 2-deoxystreptamine (2-DOS) ring or the sugar ring were designed and synthesized. The synthetic approach involved the construction of 2-DOS derivatives by catalytic Ferrier II rearrangement, stereo- and regio-selective functional group transformations, glycosyl coupling reaction, and global deprotection. Of the synthetic neamine analogues, four compounds showed comparable 16S rRNA binding affinities with neamine, whereas they displayed lower binding affinities towards 18S rRNA than neamine, implying a lower toxicity to mammals. This strategy might have applications in the chemical synthesis of other neamine derivatives and new aminoglycoside antibiotics with improved biological activities.

语种英语
WOS记录号WOS:000270320300017
引用统计
被引频次:21[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/400002259/52058
专题北京大学药学院
北京大学药学院_药物化学系
作者单位1.Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.Peking Univ, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Pang, Li-Juan,Wang, Dan,Zhou, Jian,et al. Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2009,7(20):4252-4266.
APA Pang, Li-Juan,Wang, Dan,Zhou, Jian,Zhang, Li-He,&Ye, Xin-Shan.(2009).Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations.ORGANIC & BIOMOLECULAR CHEMISTRY,7(20),4252-4266.
MLA Pang, Li-Juan,et al."Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations".ORGANIC & BIOMOLECULAR CHEMISTRY 7.20(2009):4252-4266.
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