该文中,研究人员报告了一种超快速生物正交连接反应物对的设计,该反应物对由空间屏蔽的磺化四唑和双环[6.1.0]非-4-yn-9-基甲醇(BCN)组成。该设计涉及在二苯基四唑的C-苯环上放置一对水溶性N-磺酰吡咯取代基,以使光诱导环加成反应优于竞争性亲核加成反应。
第一性原理计算为四唑-BCN环加成反应的起源提供了重要的见解,与四唑-spirohexene环加成反应相比,四唑-BCN环加成反应具有更高的动力学性能。四唑-BCN环加成还可以在短短15秒内实现活细胞上胰高血糖素受体的快速生物正交标记。
附:英文原文
Title: Superfast Tetrazole–BCN Cycloaddition Reaction for Bioorthogonal Protein Labeling on Live Cells
Author: Gangam Srikanth Kumar, Stefano Racioppi, Eva Zurek, Qing Lin
Issue&Volume: December 29, 2021
Abstract: Here we report the design of a superfast bioorthogonal ligation reactant pair comprising a sterically shielded, sulfonated tetrazole and bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN). The design involves placing a pair of water-soluble N-sulfonylpyrrole substituents at the C-phenyl ring of diphenyltetrazoles to favor the photoinduced cycloaddition reaction over the competing nucleophilic additions. First-principles computations provide vital insights into the origin of the tetrazole–BCN cycloaddition’s superior kinetics compared to the tetrazole–spirohexene cycloaddition. The tetrazole–BCN cycloaddition also enabled rapid bioorthogonal labeling of glucagon receptors on live cells in as little as 15 s.
DOI: 10.1021/jacs.1c10354
Source: https://pubs.acs.org/doi/10.1021/jacs.1c10354
JACS:《美国化学会志》,创刊于1879年。隶属于美国化学会,最新IF:14.612
官方网址:https://pubs.acs.org/journal/jacsat
投稿链接:https://acsparagonplus.acs.org/psweb/loginForm?code=1000