杂环扩展嘌呤核苷。设计、合成及初步生物活性
Hetero-expanded purine nucleosides. Design, synthesis and preliminary biological activity.
作者信息
Seley-Radtke Katherine L, Zhang Zhibo, Wauchope Orrette R, Zimmermann Sarah C, Ivanov Alexander, Korba Brent
机构信息
University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, MD 21250, USA.
出版信息
Nucleic Acids Symp Ser (Oxf). 2008(52):635-6. doi: 10.1093/nass/nrn321.
Abstract
Several thieno-expanded purine nucleoside analogues were synthesized for use as tools in ongoing investigations into nucleic acid structure and function in our laboratories. The inclusion of the thiophene ring system in the nucleoside endows the purine scaffold with advantages not previously available in other reported expanded purines. The synthesis and preliminary biological studies are reported herein.
摘要
我们实验室合成了几种噻吩扩展的嘌呤核苷类似物，用作正在进行的核酸结构与功能研究的工具。核苷中噻吩环系统的引入赋予嘌呤骨架一些在其他已报道的扩展嘌呤中未曾有过的优势。本文报道了其合成及初步生物学研究。
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本文引用的文献
1
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J Am Chem Soc. 1996 Aug 28;118(34):8182-8183. doi: 10.1021/ja961733f.
2
Factors Contributing to Aromatic Stacking in Water: Evaluation in the Context of DNA.水中芳香堆积的影响因素：在DNA背景下的评估
J Am Chem Soc. 2000 Feb 10;122(10):2213-2222. doi: 10.1021/ja9934854.
3
A computational study of expanded heterocyclic nucleosides in DNA.DNA中扩展杂环核苷的计算研究。
J Biomol Struct Dyn. 2008 Dec;26(3):283-92. doi: 10.1080/07391102.2008.10507243.
4
Model systems for understanding DNA base pairing.用于理解DNA碱基配对的模型系统。
Curr Opin Chem Biol. 2007 Dec;11(6):588-94. doi: 10.1016/j.cbpa.2007.09.019. Epub 2007 Nov 9.
5
Synthesis and properties of size-expanded DNAs: toward designed, functional genetic systems.尺寸扩展DNA的合成与性质：迈向设计的功能性遗传系统
Acc Chem Res. 2007 Feb;40(2):141-50. doi: 10.1021/ar068200o.
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Toward a designed, functioning genetic system with expanded-size base pairs: solution structure of the eight-base xDNA double helix.迈向具有扩展碱基对的设计型功能遗传系统：八碱基xDNA双螺旋的溶液结构
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7
Exploring the limits of DNA size: naphtho-homologated DNA bases and pairs.探索DNA大小的极限：萘同系化DNA碱基与碱基对。
J Am Chem Soc. 2006 Jul 19;128(28):9219-30. doi: 10.1021/ja0619004.
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J Org Chem. 2005 Mar 4;70(5):1612-9. doi: 10.1021/jo048218h.
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J Am Chem Soc. 2005 Feb 9;127(5):1396-402. doi: 10.1021/ja046305l.
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