Exceptionally rapid oxime and hydrazone formation promoted by catalytic amine buffers with low toxicity†,Chemical Science

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Exceptionally rapid oxime and hydrazone formation promoted by catalytic amine buffers with low toxicity†
Chemical Science ( IF 7.6 ) Pub Date : 2018-05-21 00:00:00 , DOI: 10.1039/c8sc01082j
Dennis Larsen _{1,

2,

3,

4} , Anna M. Kietrys _{1,

2,

3,

4} , Spencer A. Clark _{1,

2,

3,

4} , Hyun Shin Park _{1,

2,

3,

4} , Andreas Ekebergh _{1,

2,

3,

4} , Eric T. Kool _{1,

2,

3,

4}

Affiliation

Hydrazone and oxime bond formation between α-nucleophiles (e.g. hydrazines, alkoxy-amines) and carbonyl compounds (aldehydes and ketones) is convenient and is widely applied in multiple fields of research. While the reactants are simple, a substantial drawback is the relatively slow reaction at neutral pH. Here we describe a novel molecular strategy for accelerating these reactions, using bifunctional buffer compounds that not only control pH but also catalyze the reaction. The buffers can be employed at pH 5–9 (5–50 mM) and accelerate reactions by several orders of magnitude, yielding second-order rate constants of >10 M⁻¹ s⁻¹. Effective bifunctional amines include 2-(aminomethyl)imidazoles and N,N-dimethylethylenediamine. Unlike previous diaminobenzene catalysts, the new buffer amines are found to have low toxicity to human cells, and can be used to promote reactions in cellular applications.

中文翻译：

低毒性的催化胺缓冲液可促进肟和的快速形成†

在α-亲核试剂（例如肼，烷氧基胺）和羰基化合物（醛和酮）之间形成和肟键很方便，并广泛应用于多个研究领域。尽管反应物很简单，但是一个主要的缺点是在中性pH下反应较慢。在这里，我们描述了一种新型的分子策略，这些分子可以使用不仅控制pH值而且可以催化反应的双功能缓冲化合物来加速这些反应。缓冲液可以在pH 5–9（5–50 mM）下使用，并将反应加速几个数量级，从而产生> 10 M ^-1 s ^-1的二级速率常数。有效的双官能胺包括2-（氨基甲基）咪唑和N，N-二甲基乙二胺。与以前的二氨基苯催化剂不同，新的缓冲胺被发现对人体细胞毒性低，可用于促进细胞应用中的反应。

更新日期：2018-05-21

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