Bioorthogonal Reactions of Oxadiazinones With Strained trans-Cyclooctenes

IF 1.9 4区化学 Q2 CHEMISTRY, ORGANIC

Journal of Physical Organic Chemistry Pub Date : 2024-12-22 DOI:10.1002/poc.4674

Kaitlyn Morrill, Jason D. Josephson, Didier A. Bilodeau, Baha Altamimi, Masaya Nakajima, John Paul Pezacki

引用次数: 0

Abstract

We report quantitative details of addition reactions of a strained trans-cyclooctene with a series of oxadiazinones, analogues of the bioorthogonally fruitful tetrazines. Both experimental and computational studies of these ligations reveal their sensitivity to differing electronic character of oxadiazinone substituents. Achieving rate constants up to 9.5 L mol⁻¹ s⁻¹, oxadiazinones demonstrate untapped potential for bioorthogonal applications.

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来源期刊

Journal of Physical Organic Chemistry 化学-物理化学

CiteScore

3.60

自引率

11.10%

发文量

161

审稿时长

2.3 months

期刊介绍： The Journal of Physical Organic Chemistry is the foremost international journal devoted to the relationship between molecular structure and chemical reactivity in organic systems. It publishes Research Articles, Reviews and Mini Reviews based on research striving to understand the principles governing chemical structures in relation to activity and transformation with physical and mathematical rigor, using results derived from experimental and computational methods. Physical Organic Chemistry is a central and fundamental field with multiple applications in fields such as molecular recognition, supramolecular chemistry, catalysis, photochemistry, biological and material sciences, nanotechnology and surface science.