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1′,5′-Anhydro-l-ribo-hexitol Adenine Nucleic Acids (α-l-HNA-A): Synthesis and Chiral Selection Properties in the Mirror Image World
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2015-04-30 00:00:00 , DOI: 10.1021/acs.joc.5b00406
Daniele D’Alonzo 1 , Mathy Froeyen 2 , Guy Schepers 2 , Giovanni Di Fabio 1 , Arthur Van Aerschot 2 , Piet Herdewijn 2 , Giovanni Palumbo 1 , Annalisa Guaragna 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2015-04-30 00:00:00 , DOI: 10.1021/acs.joc.5b00406
Daniele D’Alonzo 1 , Mathy Froeyen 2 , Guy Schepers 2 , Giovanni Di Fabio 1 , Arthur Van Aerschot 2 , Piet Herdewijn 2 , Giovanni Palumbo 1 , Annalisa Guaragna 1
Affiliation
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The synthesis and a preliminary investigation of the base pairing properties of (6′ → 4′)-linked 1′,5′-anhydro-l-ribo-hexitol nucleic acids (α-l-HNA) have herein been reported through the study of a model oligoadenylate system in the mirror image world. Despite its considerable preorganization due to the rigidity of the “all equatorial” pyranyl sugar backbone, α-l-HNA represents a versatile informational biopolymer, in view of its capability to cross-communicate with natural and unnatural complements in both enantiomeric forms. This seems the result of an inherent flexibility of the oligonucleotide system, as witnessed by the singular formation of iso- and heterochiral associations composed of regular, enantiomorphic helical structures. The peculiar properties of α-l-HNA (and most generally of the α-HNA system) provide new elements in our understanding of the structural prerequisites ruling the stereoselectivity of the hybridization processes of nucleic acids.
中文翻译:
1',5'-脱水-1-核糖-己糖醇腺嘌呤核酸(α-1-HNA-A):镜像世界中的合成和手性选择性质
的合成和(6'→4')中的碱基配对特性的初步研究-联1',5'-脱水-升-核糖-hexitol核酸(α-升-HNA)已在本文已通过研究报告镜像世界中模型寡聚腺苷酸体系的结构。尽管由于“所有赤道”吡喃糖主链α- 1的刚性而进行了相当大的预组织鉴于其与两种对映体形式的天然和非天然补体交叉交流的能力,-HNA代表了一种多功能的信息生物聚合物。这似乎是寡核苷酸系统固有的灵活性的结果,这是由规则的,对映体的螺旋结构组成的异手性和异手性缔合的奇异形成所证明的。α-的特殊属性升-HNA(并且最通常α-HNA系统的)提供在我们的结构的先决条件统治的核酸杂交过程的立体选择性的理解新的元素。
更新日期:2015-04-30
中文翻译:
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1',5'-脱水-1-核糖-己糖醇腺嘌呤核酸(α-1-HNA-A):镜像世界中的合成和手性选择性质
的合成和(6'→4')中的碱基配对特性的初步研究-联1',5'-脱水-升-核糖-hexitol核酸(α-升-HNA)已在本文已通过研究报告镜像世界中模型寡聚腺苷酸体系的结构。尽管由于“所有赤道”吡喃糖主链α- 1的刚性而进行了相当大的预组织鉴于其与两种对映体形式的天然和非天然补体交叉交流的能力,-HNA代表了一种多功能的信息生物聚合物。这似乎是寡核苷酸系统固有的灵活性的结果,这是由规则的,对映体的螺旋结构组成的异手性和异手性缔合的奇异形成所证明的。α-的特殊属性升-HNA(并且最通常α-HNA系统的)提供在我们的结构的先决条件统治的核酸杂交过程的立体选择性的理解新的元素。