O6-(二-1-) 氨酸衍生物:易于合成的,反应性核酸
Suyeal Bae1, Mahesh K Lakshman
1Department of Chemistry, The City College and The City University of New York, 138th Street at Convent Avenue, New York, New York 10031-9198, USA.
Journal of the American Chemical Society
|January 25, 2007
概括
一种新方法合成了从氨酸和BOP试剂中获得的O6-(二-1-) 氨酸衍生物. 这些稳定的核酸衍生物对SNR反应和DNA修饰有效.
科学领域:
- 有机化学 有机化学
- 核酸化学 核酸化学
- 药用化学 医学化学
背景情况:
- 伊诺辛和2'-脱氧伊诺辛是基本的核酸.
- 开发新的核酸衍生物对于化学生物学和药物发现至关重要.
- 修改核酸的高效合成途径非常受欢迎.
研究的目的:
- 开发一种新且方便的方法来合成O6-(二-1-) 氨酸及其2'-脱氧衍生物.
- 探索这些新型核酸衍生物的反应性.
- 准备和评估一个DNA构建块,用于特定站点的DNA修饰.
主要方法:
- 氨酸或2'-脱氧氨酸与1H-二醇-1-氧三 (dimethylamino) 六酸 (BOP) 的反应.
- 使用像31P{1H} NMR.这样的技术来隔离和描述中间体和产品.
- 合成各种核酸衍生物,包括二元和合物.
- 用于DNA合成的光胺基构建块的制备.
主要成果:
- 成功合成了一种新型类型的O6-(二-1-) 氨酸和2'-脱氧氨酸氨酸衍生物.
- 这些衍生物作为有效的电友核化物,易于与各种核友反应.
- 实现了复杂的结构,如基桥接二元和核酸-氨基酸结合物.
- 制备了一种胺酸衍生物,并显示出对特定位点的DNA修饰的潜力.
结论:
- 一种单一的,简单的方法可以产生稳定,有反应性的 ribo 和 2'-deoxyribonucleoside 衍生物.
- 这些O6-(二-1-) 氨酸衍生物是SNR化学的多功能合成物.
- 班佐特醇核酸酸胺是DNA修饰的一个有前途的试剂.
更多相关视频
相关概念视频
Organic Compounds
All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Aldehydes and Ketones with Alcohols: Hemiacetal Formation
Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
Carboxylic Acid Derivatives: Overview
Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.


