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Issue 15, 2018
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α-Methyl phenylglycines by asymmetric α-arylation of alanine and their effect on the conformational preference of helical Aib foldamers

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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

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Supplementary files

Article information


Submitted
05 Mar 2018
Accepted
22 Mar 2018
First published
26 Mar 2018

Org. Biomol. Chem., 2018,16, 2757-2761
Article type
Paper

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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