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学科主题: 药学
题名:
Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations
作者: Pang, Li-Juan1; Wang, Dan1; Zhou, Jian1; Zhang, Li-He1; Ye, Xin-Shan1
刊名: ORGANIC & BIOMOLECULAR CHEMISTRY
发表日期: 2009
DOI: 10.1039/b907518f
卷: 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
项目资助者: National Natural Science Foundation of China ; Ministry of Science and Technology of China
WOS记录号: WOS:000270320300017
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/52058
Appears in Collections:北京大学药学院_期刊论文

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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

Recommended Citation:
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.
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