Department of Chemistry, The University of Hong Kong, Hong Kong, PR China.
Department of Chemistry, The University of Hong Kong, Hong Kong, PR China.
Methods Enzymol. 2020;639:237-261. doi: 10.1016/bs.mie.2020.04.016. Epub 2020 May 4.
Ortho-Phthalaldehyde (OPA)-amine reaction and OPA-amine-thiol reaction have been developed to effectively modify native peptides and proteins under the physiological conditions. First, OPA and its derivatives can rapidly and smoothly react with primary amine moieties in peptides and proteins to achieve native protein biconjugations. Furthermore, OPA-alkyne bifunctional linkers can be used for proteome profiling. Second, OPA-amine-thiol three-component reaction has been developed for chemoselective peptide cyclization, directly on unprotected peptides in the aqueous buffer. Moreover, this OPA-guided cyclic peptide can be further modified with the N-maleimide moiety in one pot to introduce additional functionalities. The development of this OPA based chemoselective bioconjugation and peptide cyclization extends the toolbox for protein chemical modification and construction of cyclic peptides.
邻苯二甲醛（OPA）-胺反应和 OPA-胺-巯基反应已被开发用于在生理条件下有效地修饰天然肽和蛋白质。首先，OPA 及其衍生物可以快速、顺利地与肽和蛋白质中的伯胺部分反应，从而实现天然蛋白质的双连接。此外，OPA-炔基双功能接头可用于蛋白质组分析。其次，已开发出 OPA-胺-巯基三组分反应，用于在水缓冲液中直接对未保护的肽进行化学选择性肽环化。此外，这种 OPA 导向的环肽可以进一步用 N-马来酰亚胺部分一锅法修饰，以引入额外的功能。这种基于 OPA 的化学选择性生物偶联和肽环化的发展扩展了蛋白质化学修饰和环状肽构建的工具包。
