Thanzeel F Yushra, Wolf Christian
Department of Chemistry, Georgetown University 37th and O Streets Washington DC 20057 USA
RSC Adv. 2021 May 25;11(31):18960-18965. doi: 10.1039/d1ra03271b. eCollection 2021 May 24.
We report chemoselective and modular peptide bioconjugation using stoichiometric amounts of 4-halocoumarin and arylsulfonate agents that undergo metal-free C(sp)-heteroatom bond formation at micromolar concentrations. The underlying -substitution click chemistry is irreversible and generates stable and inherently fluorescent bioconjugates, and the broad selection of coumarin tags offers high labeling flexibility and versatility. Different coumarins and arylsulfonates can be selectively attached to amino and thiol groups in the small peptides glutathione and ornipressin, and both free as well as latent thiols captured in disulfide bridges can be targeted if desired. The broad utility, ease of use, storage, and preparation of 4-halocoumarins and arylsulfonates are very attractive features that extend currently available dual bioconjugation capabilities.
我们报道了使用化学计量的4-卤代香豆素和芳基磺酸盐试剂进行化学选择性和模块化肽生物共轭，这些试剂在微摩尔浓度下发生无金属的C(sp)-杂原子键形成。潜在的β-取代点击化学是不可逆的，并产生稳定且固有荧光的生物共轭物，香豆素标签的广泛选择提供了高标记灵活性和多功能性。不同的香豆素和芳基磺酸盐可以选择性地连接到小肽谷胱甘肽和鸟加压素中的氨基和硫醇基团上，如果需要，二硫键桥中捕获的游离以及潜在硫醇都可以作为目标。4-卤代香豆素和芳基磺酸盐的广泛实用性、易用性、储存性和制备性是非常有吸引力的特性，扩展了目前可用的双重生物共轭能力。
