Leiden Institute of Chemistry, and The Institute for Chemical Immunology, Leiden University, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.
Chemistry. 2018 Dec 5;24(68):18075-18081. doi: 10.1002/chem.201803839. Epub 2018 Nov 8.
The inverse-electron-demand Diels-Alder/pyridazine elimination tandem reaction, in which the allylic substituent on trans-cyclooctene is eliminated following reaction with tetrazines, is gaining interest as a versatile bioorthogonal process. One potential shortcoming of such currently used reactions is their propensity to proceed faster and more efficiently at lower pH, a feature caused by the nature of the tetrazines used. Here, we present aminoethyl-substituted tetrazines as the first pH-independent reagents showing invariably fast elimination kinetics at all biologically relevant pH values.
逆电子需求 Diels-Alder/哒嗪消除串联反应，其中反式环辛烯上的烯丙基取代基与四嗪反应后被消除，作为一种通用的生物正交反应过程引起了人们的兴趣。目前使用的此类反应的一个潜在缺点是它们在较低 pH 值下更快、更有效地进行，这一特性是由所使用的四嗪的性质引起的。在这里，我们提出了氨基乙基取代的四嗪作为第一个 pH 独立的试剂，在所有生物学相关的 pH 值下始终表现出快速的消除动力学。
