Department of Applied Chemistry and Biochemical Engineering, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8561, Japan.
Course of Applied Chemistry and Biochemical Engineering, Department of Engineering, Graduate School of Integrated Science and Technology, Shizuoka University, 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8561, Japan.
Org Lett. 2021 Mar 5;23(5):1653-1658. doi: 10.1021/acs.orglett.1c00074. Epub 2021 Feb 11.
A novel late-stage solubilization of peptides using hydrazides is described. A solubilizing tag was attached through a selective N-alkylation at a hydrazide moiety with the aid of a 2-picoline-borane complex in 50% acetic acid-hexafluoro-2-propanol. The tag, which tolerates ligation and desulfurization conditions, can be detached by a Cu-mediated selective oxidative hydrolysis of the -alkyl hydrazide. This new method was validated through the synthesis of HIV-1 protease.
本文描述了一种使用酰肼实现多肽晚期增溶的新方法。通过在 50%乙酸-六氟-2-丙醇中使用 2-吡啶硼烷复合物选择性地对酰肼部分进行 N-烷基化，将一个增溶标签连接到酰肼上。该标签耐受连接和脱硫条件，可以通过 Cu 介导的 -烷基酰肼的选择性氧化水解来去除。该新方法通过 HIV-1 蛋白酶的合成得到了验证。
