2-Hydroxy-4-methoxybenzyl as a Thiol-Protecting Group for Directed-Disulfide Bond Formation.

Autor: Zoukimian C; Univ. Grenoble Alpes, CNRS, Department of Molecular Chemistry, 570 rue de la chimie, CS 40700, Grenoble 38000, France.; Smartox Biotechnology, 6 rue des platanes, Saint-Egrève 38120, France., Béroud R; Smartox Biotechnology, 6 rue des platanes, Saint-Egrève 38120, France., Boturyn D; Univ. Grenoble Alpes, CNRS, Department of Molecular Chemistry, 570 rue de la chimie, CS 40700, Grenoble 38000, France.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2022 May 13; Vol. 24 (18), pp. 3407-3410. Date of Electronic Publication: 2022 May 02.
DOI: 10.1021/acs.orglett.2c01190
Abstrakt: The chemical synthesis of disulfide-rich peptides such as toxins can be accomplished by using numerous orthogonal cysteine-protecting groups. Herein we report the use of the Hmb off/on protecting group for directed disulfide bond formation. Its combination with classical Trt, Acm, and Mob groups was studied for the synthesis of NMB-1 and phlotoxin-1 toxins highlighting new orthogonal strategies for directed disulfide bond formation.
Databáze: MEDLINE