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构象受限的 N-甲撑基-dT 类似物在 DNA 发夹结构中呈现出一种出人意料的 C4'-外式糖环构象。

The conformationally constrained N-methanocarba-dT analogue adopts an unexpected C4'-exo sugar pucker in the structure of a DNA hairpin.

机构信息

Department of Biochemistry, Vanderbilt University, School of Medicine, Nashville, Tennessee 37232, United States.

出版信息

Biochemistry. 2012 Apr 3;51(13):2639-41. doi: 10.1021/bi300215k. Epub 2012 Mar 20.

Abstract

Incorporation of a bicyclo[3.1.0]hexane scaffold into the nucleoside sugar was devised to lock the embedded cyclopentane ring in conformations that mimic the furanose North and South sugar puckers. To analyze the effects of North-methanocarba-2'-deoxythymidine (N-MCdT) on the B-form DNA, we crystallized d(CGCGAA[mcTmcT]CGCG) with two N-MCdTs. Instead of a duplex, the 12mer forms a tetraloop hairpin, whereby loop N-MCdTs adopt the C4'-exo pucker (NE; P = 50°). Thus, the bicyclic framework does not limit the pucker to the anticipated C2'-exo range (NNW; P = -18°).

摘要

将双环[3.1.0]己烷骨架引入核苷糖中,以将嵌入的环戊烷环锁定在模拟呋喃糖 North 和 South 糖构象的构象中。为了分析 North-甲叉基-2'-脱氧胸苷(N-MCdT)对 B 型 DNA 的影响,我们用两个 N-MCdT 对 d(CGCGAA[mcTmcT]CGCG)进行了结晶。12 mer 形成四环发夹,而不是双链体,其中环 N-MCdT 采用 C4'-外式构象(NE;P = 50°)。因此,双环骨架不会将构象限制在预期的 C2'-外式范围(NNW;P = -18°)内。

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