Organic and Biomolecular Chemistry p. 4986 - 4991 (2021)
Update date:2022-08-30
Topics:
Han, Gun Su
Domaille, Dylan W.
Dynamic bonds continually form and dissociate at equilibrium. Carbonyl compounds with proximal boronic acids, including 2-formylphenylboronic acid (2-FPBA), have been reported to form highly dynamic covalent hydrazone and oxime bonds in physiological conditions, but strategies to tune the dynamics have not yet been reported. Here, we characterize the dynamics of 2-FPBA-derived hydrazones and oximes and account for both the rapid rate of formation (~102-103M?1s?1) and the relatively fast rate of hydrolysis (~10?4s?1) at physiological pH. We further show that these substrates undergo exchange with α-nucleophiles, which can be reversibly paused and restarted with pH control. Finally, we show that oxidation of the arylboronic acid effectively abolishes the rapid dynamics, which slows the forward reaction by more than 30?000 times and increases the hydrolytic half-life from 50 minutes to 6 months at physiological pH. These results set the stage to explore these linkages in dynamic combinatorial libraries, reversible bioconjugation, and self-healing materials.
View MoreChengdu Biopurify Phytochemicals Ltd.
website:http://www.phytopurify.com
Contact:+86-28-82633397
Address:2F,No.11 Building,No.388 Rongtaidadao CNSTP,Wenjiang Zone,Chengdu,Sichuan, China
Shanxi Tongji Pharmaceuticals Co., Ltd.
Contact:+86-359-3024784
Address:Xikuang South Road, Ruicheng County , Shanxi
website:http://www.maisonchem.com.cn
Contact:0086-311-83833777
Address:Leitou industrial district, xinji, shijiazhuang city, hebei province,
ChangZhou XiaQing Chemical Co., Ltd.
Contact:+86-519-88721665
Address:3# Hengluo Road, Henglin Town, Changzhou City, Jiangsu Province,China
Suzhou Wedo Chemicals Co., Ltd.
Contact:86 512 58100425
Address:Zonger Road, DongSha Industry Park , Zhangjiagang, Jiangsu, China
Doi:10.1002/ardp.19823150708
(1982)Doi:10.1021/ja00447a035
(1977)Doi:10.1002/aoc.3087
(2014)Doi:10.1016/j.materresbull.2008.01.003
(2008)Doi:10.1002/anie.201706549
(2017)Doi:10.1246/cl.1992.743
(1992)