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Journal of Chemical Crystallography

, Volume 41, Issue 9, pp 1328–1334 | Cite as

X-Ray Crystallographic Structure and Absolute Configuration of the Cyclic Di-amino Acid Peptide: Cyclo(l-HomoCySH-l-HomoCySH)

  • Andrew P. Mendham
  • John Spencer
  • Babur Z. Chowdhry
  • Trevor J. Dines
  • Muhammad Mujahid
  • Rex A. Palmer
  • Graham J. Tizzard
  • Simon J. Coles
Original Paper
  • 112 Downloads

Abstract

The cyclic di-amino acid peptide cyclo(l-homoCySH-l-homoCySH) [(3S, 6S)-3, 6-bis(2-sulfanylethyl) piperazine-2,5-dione, C8H14N2O2S2, crystallizes in the orthorhombic space group P212121 with unit cell parameters a = 6.1509(2) Å, b = 18.0217(9) Å, c = 29.6166(14) Å, V = 3283.0(2) Å3, Z = 12 (3 molecules, A, B and C, per asymmetric unit), D c = 1.422 g cm−3 and a linear absorption coefficient of 0.464 mm−1. The crystal structure determination was carried out with MoKα X-ray data measured at 120(2) K. In the final refinement cycle the data/restraints/parameter ratios were 5595/0/385 and goodness-of-fit on F 2 = 1.084. Final R indices for [I > 2sigma(I)] were R1 = 0.0746, wR2 = 0.1356 and R indices (all data) R1 = 0.1092, wR2 = 0.1529. The largest electron density difference peak and hole were 0.526 and −0.445e Å−3. The DKP rings in all three molecules are essentially, and unusually, planar and the C=O oxygen atoms are co-planar with the ring in each case. Ring atom rms deviations, including the =O groups, are 0.0668, 0.0658 and 0.0656 Å in molecules A, B and C, respectively. Details of the molecular geometry are compared with the compound cyclo(Gly-Gly) (Degeilh R, Marsh RE Acta Cryst 12:1007, 1959) and in addition some cyclic di-amino acid peptides in which the DKP rings have more puckered boat conformations.

Graphical Abstract

The crystal structure of the cyclic di-amino acid peptide: cyclo(l-homoCySH-l-homoCySH) at 120 K is presented. There are three independent molecules A, B and C, per asymmetric unit in space group P212121 which is a rare occurrence. The DKP rings in all three molecules, with the exception of the H atoms, are essentially, and unusually, planar and the C=O oxygen atoms are co-planar with the ring in each case. Ring atom rms deviations, including the =O groups, are 0.0668, 0.0658 and 0.0656 Å in molecules A, B and C, respectively.

Drawn with Ortep/Raster [22, 23]

Keywords

Cyclic di-amino acid peptide Cyclic dipeptides X-ray crystal structure Absolute configuration DKP ring conformations 

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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Andrew P. Mendham
    • 1
  • John Spencer
    • 1
  • Babur Z. Chowdhry
    • 1
  • Trevor J. Dines
    • 2
  • Muhammad Mujahid
    • 1
  • Rex A. Palmer
    • 4
  • Graham J. Tizzard
    • 3
  • Simon J. Coles
    • 3
  1. 1.School of ScienceUniversity of GreenwichKentUK
  2. 2.Division of Electronic Engineering and PhysicsUniversity of DundeeDundeeUK
  3. 3.UK National Crystallographic Service, School of ChemistryUniversity of SouthamptonSouthamptonUK
  4. 4.School of Crystallography, Birkbeck CollegeUniversity of LondonLondonUK

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