Issue 15, 2018

α-Methyl phenylglycines by asymmetric α-arylation of alanine and their effect on the conformational preference of helical Aib foldamers

Abstract

α-Arylated alanine derivatives were made enantioselectively by migratory rearrangement of a urea derivative using (R,R)-pseudoephedrine as a chiral auxiliary. Incorporation of a single residue of the product α-methyl phenylglycine into an otherwise achiral oligomer of aminoisobutyric acid oligomer induced a preferred screw sense, detectable by a NMR reporter located at the remote terminus of the oligomer. The magnitude of the screw sense induction was greater when the chiral residue was located at the N-terminus of the foldamer, and in some cases the sense of induction was opposite to that of related α-methylated amino acids with α-substituents other than aryl.

Graphical abstract: α-Methyl phenylglycines by asymmetric α-arylation of alanine and their effect on the conformational preference of helical Aib foldamers

Supplementary files

Article information

Article type
Paper
Submitted
05 Mar 2018
Accepted
22 Mar 2018
First published
26 Mar 2018

Org. Biomol. Chem., 2018,16, 2757-2761

α-Methyl phenylglycines by asymmetric α-arylation of alanine and their effect on the conformational preference of helical Aib foldamers

R. Costil, F. Fernández-Nieto, R. C. Atkinson and J. Clayden, Org. Biomol. Chem., 2018, 16, 2757 DOI: 10.1039/C8OB00551F

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