Issue 38, 2020

Facile synthesis of sulfotyrosine-containing α-conotoxins

Abstract

α-Conotoxins (Ctx) can selectively target distinct subtypes of nicotinic acetylcholine receptors (nAChRs), which are closely related to a number of neurological diseases, and they have been considered as ideal probes and model peptide drugs. Sulfotyrosine (sY) is an important post-translational modification and believed to modulate certain key protein–protein interactions. Although sY modification has been indicated in several α-Ctx, its biological consequence has largely remained unexplored, mostly because of the difficulties in both its extraction from biological samples and chemical synthesis. Herein, we report a facile synthesis and folding strategy for obtaining the sY modified α-Ctx. This strategy is based on the development of a simple and controlled deprotection of the neopentyl protecting group of the sulfate ester as well as its compatibility with a step-wise oxidative folding of the two disulfide bonds. Eight sY modified α-Ctx peptides were successfully synthesized in good yield and with high purity, and their serum stabilities were almost comparable with non-modified peptides.

Graphical abstract: Facile synthesis of sulfotyrosine-containing α-conotoxins

Supplementary files

Article information

Article type
Paper
Submitted
24 jul 2020
Accepted
09 set 2020
First published
10 set 2020

Org. Biomol. Chem., 2020,18, 7559-7564

Facile synthesis of sulfotyrosine-containing α-conotoxins

C. Li and C. He, Org. Biomol. Chem., 2020, 18, 7559 DOI: 10.1039/D0OB01526A

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