氧氨盐介导的DNA上酒精氧化用于DEL合成
Pratik R Chheda1, Nicholas Simmons1, Zhicai Shi2
1Discovery Chemistry, Janssen Research & Development, LLC, San Diego, California 92121, United States.
Organic letters
|July 30, 2024
概括
我们开发了一种新方法,在室温下将DNA链接的酒精转化为碳素酸. 这促进了DNA编码库的合成,通过使新的化学构建块成为可能.
科学领域:
- 有机化学 有机化学
- 药用化学 医学化学
- 合成化学 合成化学
背景情况:
- 在DNA上碳素酸对于合成DNA编码库 (DEL) 至关重要.
- 目前生产这些中间体的方法可能是有限的.
- 扩大DEL的化学多样性需要新的合成策略.
研究的目的:
- 报告一种新的,温和的氧化方法,用于生成DNA上碳素酸.
- 为了证明这种方法与DNA编码库编码策略的兼容性.
- 为了在DEL合成中使用以前无法获得的双功能碳酸中间体.
主要方法:
- 使用氧氨盐催化剂将初级酒精氧化为碳酸.
- 室温,溶液相反应条件.
- 适用于用于DEL构造的DNA链接基板.
主要成果:
- 成功氧化各种与DNA相关联的阿利法,基和异基醇.
- 与标准的DEL编码协议证明了兼容性.
- 促进了未受保护的酒精作为掩盖的碳酸盐的使用.
结论:
- 报告的方法提供了一种通用且高效的途径,可以获得DNA上碳酸酸.
- 这种进步通过增加可访问的化学多样性来扩大DNA编码库的实用性.
- 该战略允许将新型双功能构建块纳入DELs.
相关概念视频
Oxidation of Alcohols
12.9K
In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
The process of oxidation in a chemical reaction is observed in any of the three forms:
12.9K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
10.0K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.0K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
5.7K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
5.7K
Preparation of Alcohols via Addition Reactions
6.2K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
6.2K
Aldol Condensation with β-Diesters: Knoevenagel Condensation
3.0K
The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
3.0K
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate
11.2K
Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
11.2K


