Dile Ozlem, Sorrentino Anthony M, Bane Susan
Istanbul Kemerburgaz University, School of Medicine, Bagcilar, Istanbul 34217 Turkey.
State University of New York at Binghamton, Department of Chemistry, Binghamton NY 13901.
Synlett. 2016 Jun;27(9):1335-1338. doi: 10.1055/s-0035-1561387. Epub 2016 Feb 17.
Bioorthogonal site-specific chemical reaction to label biomolecules and in living cells is one of the most powerful and convenient tools in chemical biology. A reactive pairs frequently used for chemical conjugation are aldehydes/ketones with hydrazines/hydrazides/hydroxylamines. Although the reaction is generally specific for the two components, even in a cellular environment, the reaction is very slow under physiological conditions. Addition of a phosphate group at the position of an aromatic aldehyde increases the reaction rate by an order of magnitude and enhances the aqueous solubility of the reagent and the product. We have synthesized phosphate-substituted aldehyde synthetic models to study kinetics of their reactions with hydrazines and hydrazides that contain a fluorophore. This rapid bioorthogonal reaction should therefore be potentially a very useful reaction for routine site-specific chemical ligations to study and image complex cellular processes in biological systems.
用于标记生物分子和活细胞的生物正交位点特异性化学反应是化学生物学中最强大、最便捷的工具之一。常用于化学共轭的反应对是醛/酮与肼/酰肼/羟胺。尽管该反应通常对这两种组分具有特异性，即使在细胞环境中，该反应在生理条件下也非常缓慢。在芳香醛的位置引入磷酸基团可使反应速率提高一个数量级，并增强试剂和产物的水溶性。我们合成了磷酸取代的醛合成模型，以研究它们与含有荧光团的肼和酰肼反应的动力学。因此，这种快速的生物正交反应对于常规的位点特异性化学连接以研究和成像生物系统中的复杂细胞过程可能是非常有用的反应。
