β-turn mimics by chemical ligation

Crecente Garcia, S., Neckebroeck, A., Clark, J. S. , Smith, B. O. and Thomson, A. R. (2020) β-turn mimics by chemical ligation. Organic Letters, 22(11), pp. 4424-4428. (doi: 10.1021/acs.orglett.0c01427) (PMID:32406695) (PMCID:PMC7304061)

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Abstract

We report a simple reductive amination protocol to ligate two peptides, while simultaneously installing a β-turn mimic at the ligation junction. This strategy uses commercially available materials, mild chemical conditions, and a chemoselective ligation reaction of unprotected peptide substrates accessed through standard solid phase methods. This system was implemented in a designed β-hairpin system, and biophysical analysis demonstrates effective mimicry of the β-turn.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Thomson, Dr Andrew and Crecente Garcia, Ms Selma and Smith, Dr Brian and Neckebroeck, Albane and Clark, Professor Stephen
Authors: Crecente Garcia, S., Neckebroeck, A., Clark, J. S., Smith, B. O., and Thomson, A. R.
College/School:College of Medical Veterinary and Life Sciences > Institute of Molecular Cell and Systems Biology
College of Medical Veterinary and Life Sciences > School of Medicine, Dentistry & Nursing
College of Science and Engineering
College of Science and Engineering > School of Chemistry
Journal Name:Organic Letters
Publisher:American Chemical Society
ISSN:1523-7060
ISSN (Online):1523-7052
Published Online:14 May 2020
Copyright Holders:Copyright © 2020 American Chemical Society
First Published:First published in Organic Letters 22(11):4424-4428
Publisher Policy:Reproduced under a Creative Commons licence

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
300156Molecular Switches as Sensors of Protein ModificationAndrew ThomsonEngineering and Physical Sciences Research Council (EPSRC)EP/R00899X/1Chemistry
304762Meta-Smart: Dynamic hybrid bio-plasmonic metamaterials.Malcolm KadodwalaEngineering and Physical Sciences Research Council (EPSRC)EP/S029168/1Chemistry