Phenylboronic Acid Linkers for Bioorthogonal Chemistry

机译：用于生物正交化学的苯基硼酸连接基

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Probing for specific biomolecules in cellular systems provides the ability to study biochemical processes and refine our understanding of living systems. Bioorthogonal chemistry develops reactive functional groups that covalently ligate molecules within living systems. This project studies a novel bioorthogonal reaction that couples phenylboronic acid derivatives and alpha-effect amines (hydrazines/hydrazides) to produce a stable boron-nitrogen heterocyclic product: a diazaborine. It was shown previously that 2-formylphenylboronic acid reacts with a hydrazine to rapidly form a stable diazaborine in aqueous solution at neutral pH. This project began development of a structure-reactivity profile for this reaction to refine it for bioorthogonal use. Presented are the effects of the nature of the hydrazine on kinetics of diazaborine formation, as well as the effects on diazaborine stability. Also presented is a method to determine the pKa of phenylboronic acid derivatives in order to study the effects of boronic acid pKa on diazaborine formation and stability.

机译：对细胞系统中特定生物分子的探测提供了研究生化过程和完善我们对生命系统的理解的能力。生物正交化学发展出反应性官能团，它们共价连接生物系统中的分子。该项目研究了一种新颖的生物正交反应，该反应将苯基硼酸衍生物和α-效应胺（肼/酰肼）偶联，生成稳定的硼氮杂环产物：重氮唑啉。先前已证明2-甲酰基苯基硼酸与肼反应以在中性pH下在水溶液中快速形成稳定的重氮茶碱。该项目开始为该反应开发结构反应性图谱，以改进其用于生物正交用途。提出了肼的性质对重氮茶碱形成动力学的影响以及对重氮茶碱稳定性的影响。还提出了一种测定苯基硼酸衍生物的pKa的方法，以研究硼酸pKa对重氮硼精形成和稳定性的影响。

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作者
Grieco, Samantha Leigh.;
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作者单位

State University of New York at Binghamton.;

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授予单位 State University of New York at Binghamton.;
学科 Biochemistry.
学位 M.S.
年度 2018
页码 85 p.
总页数 85
原文格式 PDF
正文语种 eng
中图分类水产、渔业;
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1. Some new N-protected amino acid derivatives of phenylboronic acid: preparation, structural chemistry and insight into structural aspects based on spectroscopic studies : Main Group Metal Chemistry [J] . Ritu Kumari Gupta, Asha Jain, Sanjiv Saxena Main Group Metal Chemistry . 2011,第3a4期

机译：苯硼酸的一些新的N保护氨基酸衍生物：制备，结构化学和对结构方面的深入了解（基于光谱研究）：主族金属化学
2. Self-recovering dual cross-linked hydrogels based on bioorthogonal click chemistry and ionic interactions [J] . Zhan Henan, Jiang Shanshan, Jonker Anika M., Journal of Materials Chemistry, B. materials for biology and medicine . 2020,第27期

机译：基于生物正交的双交联水凝胶自恢复双交联水凝胶，从而实现化学和离子相互作用
3. Single-Stranded DNA as a Cleavable Linker for Bioorthogonal Click Chemistry-Based Proteomics [J] . Tianqing Zheng, Hao Jiang, Peng Wu Bioconjugate Chemistry . 2013,第6期

机译：单链DNA作为基于生物点击化学的蛋白质组学的可裂解连接子
4. Interaction of boric acid and phenylboronic acid with cross-linked dextran gel matrix [C] . Yoshinobu Miyazaki, Kei Asada, Yuma Kawasaki 日本化学会春季年会講演予稿集 . 2018

机译：硼酸和苯基硼酸与交联葡聚糖基质的相互作用
5. Structure-Stability Studies of the Reaction between Ortho-Carbonyl Phenylboronic Acids and Hydrazides for Bioorthogonal Applications [D] . Ghosh, Saptarshi. 2021

机译：正交 - 羰基苯基苯甲酸和生物正交应用肼的反应的结构 - 稳定性研究
6. Single-stranded DNA as a Cleavable Linker for Bioorthogonal Click Chemistry-based Proteomics [O] . Tianqing Zheng, Hao Jiang, Peng Wu -1

机译：单链DNA作为基于生物点击化学的蛋白质组学的可裂解连接子
7. Self-recovering dual cross-linked hydrogels based on bioorthogonal click chemistry and ionic interactions [O] . Henan Zhan, Shanshan Jiang, Anika M. Jonker, 2020

机译：基于Bioorthogonal Click化学和离子相互作用的自恢复双交联水凝胶

Phenylboronic Acid Linkers for Bioorthogonal Chemistry

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