Conformational studies of bis(cyclic tetrapeptide), S,S'-bis(cyclo(Gly-L-hemiCys-Sar-L-Pro)). A proposed castanet-type structure in a dimethyl sulfoxide solution.

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概要

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• A bis(cyclic tetrapeptide), <I>S</I>,<I>S</I>′-bis[cyclo(Gly–L-hemiCys–Sar–L-Pro)] (BCGCSP), was prepared by coupling two homodetic cyclotetrapeptide. The conformations of BCGCSP in solutions were investigated by means of NMR, Raman, and CD spectroscopy. The <SUP>1</SUP>H-NMR data in dimethyl-<I>d</I><SUB>6</SUB> sulfoxide (Me<SUB>2</SUB>SO-<I>d</I><SUB>6</SUB>) demonstrated that the two cyclic skeletons of BCGCSP take the same conformations as that of an authentic cyclic tetrapeptide, cyclo[Gly–L-Cys(Bzl(OMe))–Sar–L-Pro] (CGCSP). The <SUP>1</SUP>H-NMR spectrum of CGCSP contains three sets of resonances, corresponding to three different molecular conformations. From the Raman lines of BCGCSP at 529 cm<SUP>−1</SUP> and 683 cm<SUP>−1</SUP> in Me<SUB>2</SUB>SO-<I>d</I><SUB>6</SUB>, it is deduced that the two HC<SUB>α</SUB>-C<SUB>β</SUB>S dihedral angles are 180°(trans), while one of the SS–C<SUB>β</SUB>C<SUB>α</SUB> dihedral angles is 20–30° and the other is either near 90° or near 180°. In addition, the values of two Raman lines predict that the C<SUB>β</SUB>S–SC<SUB>β</SUB> dihedral angle is in the range of near 90°. Such a conformation around the C<SUB>β</SUB>S–SC<SUB>β</SUB> bond is also reasonable in the light of the presence of a CD transition (CS–SC) at λ>250 nm in water. By combining the above data, the CPK molecular model of BCGCSP was constructed. An inspection of the model reveals that this bis(cyclic tetrapeptide) is likely to adopt a "castanet-type" structure in Me<SUB>2</SUB>SO-<I>d</I><SUB>6</SUB>. At the same time the individual cyclic skeleton is considered to take three different ring conformations in equilibrium.

• 公益社団法人 日本化学会の論文

著者

• TSUDA Keishiro

  Research Institute for Polymers and Textiles

• TANAKA Yoshio

  Research and Development Center, Shinryo Corporation

• Shimizu Toshimi

  Research Institute for Polymers and Textiles

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