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Full Solution-Phase Synthesis of Acetyl Hexapeptide-3 by Fragments Coupling Strategy

Author:
Zhang, Teng, Song, Wei, Zhao, Jinli, Liu, Jianli
Source:
Industrial & engineering chemistry process design and development 2017 v.56 no.41 pp. 11697-11704
ISSN:
1520-5045
Subject:
botulinum toxin, process design, synthesis
Abstract:
Acetyl hexapeptide-3, a competitive SNAP-25 inhibitor that mimics the action of botulinum neurotoxins but is nontoxic, was successively synthesized in a solution by peptide chemistry with a “3+2+1” fragment coupling strategy. The difficulties encountered in the convergent route, an optimization on scalable process, and controls on potential epimerization are systematically discussed. Final purification led to the target product’s overall 36.5% yield with 98.3% purity and excellent optical purity.
Agid:
6010126