Cycloadditions of Trans-Cyclooctenes and Nitrones as Tools for Bioorthogonal Labelling.,ChemBioChem

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Cycloadditions of Trans-Cyclooctenes and Nitrones as Tools for Bioorthogonal Labelling.
ChemBioChem ( IF 2.6 ) Pub Date : 2019-11-27 , DOI: 10.1002/cbic.201900627
Kaitlyn D Margison ₁ , Didier A Bilodeau ₁ , Farnaz Mahmoudi ₁ , John Paul Pezacki ₁

Affiliation

Trans-cyclooctenes (TCOs) represent interesting and highly reactive dipolarophiles for organic transformations including bioorthogonal chemistry. Herein we show that TCOs react rapidly with nitrones and that these reactions are bioorthogonal. Kinetic analysis of acyclic and cyclic nitrones with strained-trans-cyclooctene (s-TCO) shows fast reactivity and demonstrates the utility of this cycloaddition reaction for bioorthogonal labelling. Labelling of the bacterial peptidoglycan layer with unnatural d-amino acids tagged with nitrones and s-TCO-Alexa488 is demonstrated. These new findings expand the bioorthogonal toolbox, and allow TCO reagents to be used in bioorthogonal applications beyond tetrazine ligations for the first time and open up new avenues for bioorthogonal ligations with diverse nitrone reactants.

中文翻译：

反式环辛烯和亚硝基的环加成作为生物正交标记的工具。

反式环辛烯（TCO）代表了有趣的，高反应性的偶极亲子，可用于有机转化，包括生物正交化学。本文中，我们显示了TCO与硝酮快速反应，并且这些反应是生物正交的。带有应变的反式环辛烯（s-TCO）的无环和环状硝酮的动力学分析显示出快速的反应活性，并证明了该环加成反应在生物正交标记中的实用性。证明了用硝酮和s-TCO-Alexa488标记的非天然d-氨基酸标记细菌肽聚糖层。这些新发现扩展了生物正交工具箱，并使TCO试剂首次在四嗪连接以外的生物正交应用中使用，并为与多种硝酮反应物进行生物正交连接开辟了新途径。

更新日期：2019-11-27

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