2H‑Azirines as Potential Bifunctional Chemical Linkers of Cysteine Residues in Bioconjugate Technology

Yang Chen,^aWenjie Yang,^aJiamin Wu,^aWangbin Sun,^aTeck-Peng Loh,^*aband Yaojia Jiang^*a

^aInstitute of Advanced Synthesis, Nanjing Tech University, Nanjing 211816, P. R. China.

^bDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 637616, Singapore.

Abstract:2H-Azirine-2-caboxamides have been designed to perform as a new type of bifunctional thiol linker under very mild reaction conditions. The cleavage of a C−N double bond of 2Hazirine furnishes an amino amide functional group in situ through a thiol addition and ring-opening process. It works with a broad scope of thiols and2H-azirines in the absence of any catalysts at room temperature. Cysteine-containing peptides have also been demonstrated to work efficiently in a completely water solution.

Org. Lett.DOI:10.1021/acs.orglett.0c00415.(2019年影响因子:6.555)

文章链接：https://pubs.acs.org/doi/10.1021/acs.orglett.0c00415.