Scalable synthesis and coupling of quaternary α-arylated amino acids: α-aryl substituents are tolerated in α-helical peptides

Leonard, Daniel J, Zieleniewski, Francis, Wellhofer, Isabelle, Baker, Emily G, Ward, John W ORCID: 0000-0001-7186-6416, Woolfson, Derek N and Clayden, Jonathan (2021) Scalable synthesis and coupling of quaternary α-arylated amino acids: α-aryl substituents are tolerated in α-helical peptides. CHEMICAL SCIENCE, 12 (27). pp. 9386-9390.

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Official URL: http://dx.doi.org/10.1039/d1sc01378e

Abstract

Quaternary amino acids are important tools for the modification and stabilisation of peptide secondary structures. Here we describe a practical and scalable synthesis applicable to quaternary alpha-arylated amino acids (Q4As), and the development of solid-phase synthesis conditions for their incorporation into peptides. Monomeric and dimeric α-helical peptides are synthesised with varying degrees of Q4A substitution and their structures examined using biophysical methods. Both enantiomers of the Q4As are tolerated in folded monomeric and oligomeric α-helical peptides, with the (<i>R</i>)-enantiomer slightly more so than the (<i>S</i>).

Item Type:	Article
Divisions:	Faculty of Science and Engineering > School of Physical Sciences
Depositing User:	Symplectic Admin
Date Deposited:	09 Dec 2021 16:38
Last Modified:	17 Oct 2023 23:31
DOI:	10.1039/d1sc01378e
Open Access URL:	https://pubs.rsc.org/en/content/articlelanding/202...
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3145094