Studies have established 3-isocyanopropyloxycarbonyl (ICPrc) moieties as bioorthogonally removable protecting groups. However, reagents to prepare ICPrc-protected amines are unstable, which critically limits the practical implementation of this chemistry. Here we report 3-isocyanopropyl (pentafluorophenyl) carbonates as bench-stable precursors for the synthesis of ICPrc-protected primary and secondary amines. The utility of the chemistry for bioconjugation applications is demonstrated by reversibly masking a lysine residue on a bioactive peptide.

中文翻译：

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生物正交可去除的 3-异氰基丙氧基羰基 (ICPrc) 保护基团的稳定前体

研究已将 3-异氰基丙氧基羰基 (ICPrc) 部分确定为生物正交可移除的保护基团。然而，制备 ICPrc 保护的胺的试剂不稳定，这严重限制了这种化学的实际实施。在这里，我们报告了 3-异氰丙基（五氟苯基）碳酸酯作为合成 ICPrc 保护的伯胺和仲胺的实验室稳定前体。通过可逆地掩蔽生物活性肽上的赖氨酸残基，证明了该化学在生物偶联应用中的效用。