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ChemInform Abstract: Methyl- and (Trifluoromethyl)alkene Peptide Isosteres: Synthesis and Evaluation of Their Potential as β-Turn Promoters and Peptide Mimetics.

✍ Scribed by P. WIPF; T. C. HENNINGER; S. J. GEIB

Publisher: John Wiley and Sons
Year: 2010
Weight: 39 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199906171

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✦ Synopsis

Methyl-and (Trifluoromethyl)

alkene Peptide Isosteres: Synthesis and Evaluation of Their Potential as β-Turn Promoters and Peptide Mimetics.

-Enantioselective synthetic approaches toward L-Ala-D-Ala (or enantiomeric) dipeptide isosteres are presented, including for the first time the preparation of a CF 3 -alkene isostere. The particularly promising convergent pathway utilizes the S N 2'-addition of cuprate reagents to alkenyl aziridines and allylic mesylates. The conformations of the isosteres are compared with the structures of parent disubstituted alkenes with a view to peptide mimetic properties.

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