Crystal Structures of Dipeptides Derived from the β-Amino Acids (1R,2S)-2-Aminocyclopentanecarboxylic Acid and (1S,2R,3S)-2-Amino-3-methylcyclopentanecarboxylic Acid

  • Elin Abraham
  • Stephen G. Davies
  • Paul M. Roberts
  • Amber L. Thompson
  • James E. Thomson
Original Paper

Abstract

Crystals of the dimeric β-peptides 13 and 20, derived from (1R,2S)-2-aminocyclopentanecarboxylic acid and (1S,2R,3S)-2-amino-3-methylcyclopentanecarboxylic acid, respectively, were synthesised and studied by X-ray diffraction in order to establish their solid state secondary structural characteristics. Compound 13 crystallises in the monoclinic space group P 21 with cell parameters of a = 5.2682(1) Å, b = 9.1211(2) Å, c = 22.4467(6) Å, β = 91.3855(9)°, V = 1078.29(4) Å3 and Z = 2. Compound 20 crystallizes in the orthorhombic space group P 212121 with cell parameters of a = 5.0968(1) Å, b = 11.5546(2) Å, c = 43.5414(8) Å, V = 2564.22(8) Å3 and Z = 4. In both cases adjacent molecules are linked by a series of N–H···O=C hydrogen bonds to form β-sheet like structures.

Graphical Abstract

The structures of two dipeptides derived from the β-amino acids (1R,2S)-2-aminocyclopentanecarboxylic acid and (1S,2R,3S)-2-amino-3-methylcyclopentanecarboxylic acid have been analysed by X-ray diffraction.

Keywords

β-Peptides β-Sheet Asymmetric synthesis Lithium amide Parallel kinetic resolution 

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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Elin Abraham
    • 1
  • Stephen G. Davies
    • 1
  • Paul M. Roberts
    • 1
  • Amber L. Thompson
    • 1
  • James E. Thomson
    • 1
  1. 1.Department of Chemistry, Chemistry Research LaboratoryUniversity of OxfordOxfordUK

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