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Issue 80, 2020

Automated solid-phase concatenation of Aib residues to form long, water-soluble, helical peptides

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Abstract

Iterative coupling of 2-aminoisobutyric acid (Aib) has been achieved rapidly and efficiently using automated solid-phase peptide synthesis, employing diisopropylcarbodiimide (DIC) in the presence of ethyl cyanohydroxyiminoacetate (Oxyma). This method has allowed the first total synthesis of the fungal antibiotic Cephaibol D, and enabled the synthesis of water-soluble oligomers of Aib containing up to an unprecedented sequence of 17 consecutive Aib residues. Conformational analysis of the Aib oligomers in aqueous solution shows a length dependence in their CD spectra, with oligomers of more than 14 Aib residues apparently adopting structured helical conformations.

Graphical abstract: Automated solid-phase concatenation of Aib residues to form long, water-soluble, helical peptides

Supplementary files

Article information


Submitted
07 Jul 2020
Accepted
02 Sep 2020
First published
02 Sep 2020

This article is Open Access

Chem. Commun., 2020,56, 12049-12052
Article type
Communication

Automated solid-phase concatenation of Aib residues to form long, water-soluble, helical peptides

F. Zieleniewski, D. N. Woolfson and J. Clayden, Chem. Commun., 2020, 56, 12049 DOI: 10.1039/D0CC04698A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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