4.8 Article

New Preorganized γ-Amino Acids as Foldamer Building Blocks

Journal

ORGANIC LETTERS
Volume 14, Issue 10, Pages 2582-2585

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol3008815

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Funding

  1. NSF [CHE-0848847]
  2. Division Of Chemistry
  3. Direct For Mathematical & Physical Scien [848847] Funding Source: National Science Foundation

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An asymmetric synthesis of two new diastereomeric gamma-amino acids is described. Both molecules contain a cyclohexyl ring to limit conformational flexibility about the C-alpha-C-beta bond; they differ in having cis vs trans stereochemistry on the ring. Residues derived from the cis gamma isomer are shown to support helical secondary structures in alpha/gamma-peptide oligomers.

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