ortho-Boronic Acid Carbonyl Compounds and Their Applications in Chemical Biology.

Autor: Haggett JG; Department of Chemistry, Colorado School of Mines, 1500 Illinois St., Golden, CO 80401, USA., Domaille DW; Department of Chemistry, Colorado School of Mines, 1500 Illinois St., Golden, CO 80401, USA.; Quantitative Biology and Engineering Program, Colorado School of Mines, 1500 Illinois St., Golden, CO 80401, USA.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Feb 01; Vol. 30 (7), pp. e202302485. Date of Electronic Publication: 2023 Dec 15.
DOI: 10.1002/chem.202302485
Abstrakt: Iminoboronates and diazaborines are related classes of compounds that feature an imine ortho to an arylboronic acid (iminoboronate) or a hydrazone that cyclizes with an ortho arylboronic acid (diazaborine). Rather than acting as independent chemical motifs, the arylboronic acid impacts the rate of imine/hydrazone formation, hydrolysis, and exchange with competing nucleophiles. Increasing evidence has shown that the imine/hydrazone functionality also impacts arylboronic acid reactivity toward diols and reactive oxygen and nitrogen species (ROS/RNS). Untangling the communication between C=N linked functionalities and arylboronic acids has revealed a powerful and tunable motif for bioconjugation chemistries and other applications in chemical biology. Here, we survey the applications of iminoboronates and diazaborines in these fields with an eye toward understanding their utility as a function of neighboring group effects.
(© 2023 Wiley-VCH GmbH.)
Databáze: MEDLINE
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