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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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Original languageEnglish
Pages (from-to)2757-2761
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number15
Early online date26 Mar 2018
DOIs
DateAccepted/In press - 22 Mar 2018
DateE-pub ahead of print - 26 Mar 2018
DatePublished (current) - 21 Apr 2018

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.

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    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via RSC at http://pubs.rsc.org/en/Content/ArticleLanding/2018/OB/C8OB00551F#!divAbstract . Please refer to any applicable terms of use of the publisher.

    Accepted author manuscript, 740 KB, PDF document

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