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One-Pot Peptide Ligation–Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides

Spengler, Jan, Blanco-Canosa, Juan B., Forni, Luciano and Albericio, Fernando (2018) One-Pot Peptide Ligation–Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides Organic Letters, 20 (14). pp. 4306-4309.

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Abstract

Native chemical ligation (NCL) employing the N-methylbenzimidazolinone (MeNbz) linker readily provided the linear precursor of a 16-mer peptide that is difficult to obtain by stepwise solid-phase peptide synthesis. NCL and the workup conditions were improved toward a protocol that allows for quantitative removal of the 4-hydroxymercaptophenol additive and subsequent formation of the disulfide bridge in the NCL cocktail by oxidation in air, tolerated by the presence of tris(hydroxypropyl)phosphine.

Item Type: Article
Divisions : Faculty of Health and Medical Sciences > School of Biosciences and Medicine
Authors :
NameEmailORCID
Spengler, Jan
Blanco-Canosa, Juan B.
Forni, Lucianol.forni@surrey.ac.uk
Albericio, Fernando
Date : 28 June 2018
DOI : 10.1021/acs.orglett.8b01741
Copyright Disclaimer : Copyright © 2018 American Chemical Society
Additional Information : This work was funded in part by the following: the Spanish Ministry of Economy, Industry, and Competitiveness (MINECO) (CTQ2015-67870-P) and the Generalitat de Catalunya (2017 SGR 1439) (Spain).
Depositing User : Diane Maxfield
Date Deposited : 29 Oct 2019 10:48
Last Modified : 29 Oct 2019 10:48
URI: http://epubs.surrey.ac.uk/id/eprint/852983

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