Grundler Verena, Gademann Karl
Department of Chemistry, University of Basel , St. Johanns-Ring 19, 4056 Basel, Switzerland.
ACS Med Chem Lett. 2014 Oct 27;5(12):1290-5. doi: 10.1021/ml5003508. eCollection 2014 Dec 11.
An efficient method for the direct labeling of the Arg guanidinium group in native peptides is reported. This straightforward procedure allows modifying the arginine moiety in peptides with various reporter groups, such as fluorophores, biotin, etc., under mild conditions in an operationally simple procedure. The scope of this method tolerates various functionalized amino acids such as His, Ser, Trp, Tyr, Glu, etc., while the only limitations uncovered so far are restricted to cysteine and free amine residues. The utility of this late-stage diversification method was demonstrated in direct labeling of leuprolide, a clinically used drug, for distribution monitoring in Daphnia, and in labeling of microcystin, a cyanobacterial toxin.
报道了一种在天然肽中直接标记精氨酸胍基的有效方法。这种简单的程序允许在温和条件下，通过操作简单的步骤，用各种报告基团（如荧光团、生物素等）修饰肽中的精氨酸部分。该方法的适用范围能够耐受各种功能化氨基酸，如组氨酸、丝氨酸、色氨酸、酪氨酸、谷氨酸等，而迄今为止发现的唯一限制仅限于半胱氨酸和游离胺残基。这种后期多样化方法的实用性在临床上使用的药物亮丙瑞林的直接标记中得到了证明，用于在水蚤中进行分布监测，以及在蓝藻毒素微囊藻毒素的标记中得到了证明。
