期刊
ORGANIC LETTERS
卷 23, 期 5, 页码 1653-1658出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00074
关键词
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资金
- JSPS KAKENHI [JP19K15712]
- Terumo Life Science Foundation
- Amano Institute of Technology
The novel late-stage solubilization of peptides using hydrazides involves attaching a solubilizing tag through selective N-alkylation at a hydrazide moiety. The tag, which can tolerate ligation and desulfurization conditions, can be detached through a Cu-mediated selective oxidative hydrolysis of the N-alkyl hydrazide. This method was validated through the synthesis of HIV-1 protease.
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 N-alkyl hydrazide. This new method was validated through the synthesis of HIV-1 protease.
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