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学科主题: 药学
题名:
Synthesis of 2-amino-2-deoxy-beta-glycosyl-(1 -> 5)-nucleosides and the interaction with RNA
作者: Zhang, GS; Guan, Z; Zhang, LR; Min, JM; Zhang, LH
刊名: BIOORGANIC & MEDICINAL CHEMISTRY
发表日期: 2003-07-31
DOI: 10.1016/S0968-0896(03)00278-5
卷: 11, 期:15, 页:3273-3278
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology
类目[WOS]: Biochemistry & Molecular Biology ; Chemistry, Medicinal ; Chemistry, Organic
研究领域[WOS]: Biochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Chemistry
关键词[WOS]: SMALL-MOLECULE DRUGS ; PENICILLIUM-BREVICOMPACTUM ; POTENT AGONISTS ; ADENOPHOSTIN-A ; TARGETING RNA ; RECOGNIZE RNA ; GLYCALS ; SULFONAMIDOGLYCOSYLATION ; OLIGOSACCHARIDES ; SUBUNITS
英文摘要:

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-galactopyranose reacted with protected nucleosides in the presence of BF3 as promoter at room temperature to give selectively 2-amino-2-deoxy-beta-glycosyl-(1-->5)nucleosides in good yields. CD spectra and thermal melting studies showed that 2-amino-2-deoxy-beta-D-glucopyranosyl-(1-->5)-nucleosides could interact with RNA in solution and 2-deoxy-2-amino-beta-D-galactopyranosyl-(1-->5)-nucleosides (17-19) exhibit higher affinity to RNA than 2-deoxy-2-amino-beta-D-glucopyranosyl-(1-->5)-nucleosides (14-16). It indicated that the majority of interactions are established between the polar group of glycosylnucleosides and the sugar-phosphate backbone of RNA helices and weak stacking interaction is observed. The different configuration of hydroxyl group on the glycosyl moiety may affect the glycosyl-nucleoside binding to RNA by induced fit. (C) 2003 Elsevier Science Ltd. All rights reserved.

语种: 英语
WOS记录号: WOS:000183935400007
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/61715
Appears in Collections:北京大学药学院_期刊论文

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作者单位: Peking Univ, Sch Pharmaceut Sci, Beijing 100083, Peoples R China

Recommended Citation:
Zhang, GS,Guan, Z,Zhang, LR,et al. Synthesis of 2-amino-2-deoxy-beta-glycosyl-(1 -> 5)-nucleosides and the interaction with RNA[J]. BIOORGANIC & MEDICINAL CHEMISTRY,2003,11(15):3273-3278.
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