Crystal and solution forms of a cyclic heptapeptide, pseudostellarin D1)

Abstract Crystal and solution forms of a cyclic heptapeptide, pseudostellarin D, cyclo(Gly-Tyr-Gly-Pro-Leu-Ile-Leu), were examined by spectroscopic evidences. A single crystal X-ray analysis showed that a revised structure, pseudostellarin D possesses a type II β-turn between Leu 7 and Gly 1 , and a type I β-turn between Pro 4 and Leu 5 . One transannular 4→1 hydrogen bond between Ile 6 -NH and Gly 3 -CO and two bifurcated hydrogen bonds between Tyr 2 -NH and Ile 6 -CO, and Gly 3 -NH and IIe 6 -CO were observed, forming a classical β-bulge unit in the crystal. The dominant solution conformation analyzed by high field NMR employing vicinal coupling constant, temperature dependence of NH protons, and ROESY spectrum was, on the whole, homologous to that observed in the solid state.

[1]  J. Briand,et al.  Conformational mobility in cyclic oligopeptides , 1993, Biopolymers.

[2]  H. Kessler,et al.  Synthesis and Solvent Effects on the Conformation of Hymenistatin 1 , 1993 .

[3]  G. N. Ramachandran,et al.  The mean geometry of the peptide unit from crystal structure data. , 1974, Biochimica et biophysica acta.

[4]  Lila M. Gierasch,et al.  Crystal structure of cyclo(Gly-L-Pro-D-Phe-Gly-Val): an example of a new type of three-residue turn , 1987 .

[5]  G Otting,et al.  Solution structure and dynamics of PEC-60, a protein of the Kazal type inhibitor family, determined by nuclear magnetic resonance spectroscopy. , 1994, Journal of molecular biology.

[6]  E. Blout,et al.  Conformational and ion binding properties of a cyclic octapeptide, cyclo(Ala‐Leu‐Pro‐Gly)2 , 1992, Biopolymers.

[7]  V. Pletnev,et al.  Molecular structures of two crystalline forms of the cyclic heptapeptide antibiotic ternatin, cyclo[-beta-OH-D-Leu-D-Ile-(NMe)Ala-(NMe)Leu-Leu-(NMe)Ala-D-(NMe)Ala-]. , 2009, International journal of peptide and protein research.

[8]  L. Gierasch,et al.  Combined use of molecular dynamics simulations and NMR to explore peptide bond isomerization and multiple intramolecular hydrogen‐bonding possibilities in a cyclic pentapeptide, cyclo (Gly‐Pro‐D‐Phe‐Gly‐Val) , 1992, Biopolymers.

[9]  T. Yamazaki,et al.  Cyclic hexapeptide analogs of somatostatin containing bridge modifications. Syntheses and conformational analyses. , 2009, International journal of peptide and protein research.

[10]  Conformations of cyclic pentapeptide endothelin receptor antagonists. , 2009, International journal of peptide and protein research.

[11]  Impact of a micellar environment on the conformations of two cyclic pentapeptides , 1992, Biopolymers.

[12]  L. Mazzarella,et al.  Stereochemical Code of Amino-Acid Residues: The Molecular Conformation of Gramicidine S , 1966, Nature.

[13]  C. Yu,et al.  NMR and dynamical simulated annealing studies on the solution conformation of urotensin II. , 1994, Biochimica et biophysica acta.

[14]  H. Hauptman,et al.  Valinomycin Crystal Structure Determination by Direct Methods , 1972, Science.

[15]  H. Morita,et al.  CONFORMATIONAL ANALYSIS OF A TYROSINASE INHIBITORY CYCLIC PENTAPEPTIDE, PSEUDOSTELLARIN A,FROM PSEUDOSTELLARIA HETEROPHYLLA , 1994 .

[16]  Horst Kessler,et al.  Conformation and Biological Activity of Cyclic Peptides , 1982 .

[17]  Structure determination of a tetrasaccharide: transient nuclear Overhauser effects in the rotating frame , 1984 .

[18]  K. Kopple,et al.  Conformations of cyclic octapeptides. 5. Crystal structure of cyclo(Cys-Gly-Pro-Phe)2 and rotating frame relaxation (T1.rho.) NMR studies of internal mobility in cyclic octapeptides , 1988 .

[19]  M. Tsuda,et al.  Hymenamides a and b, new proline-rich cyclic heptapeptides from the okinawan marine sponge hymeniacidon sp. , 1993 .

[20]  H. Morita,et al.  Pseudostellarins D - F, new tyrosinase inhibitory cyclic peptides from Pseudostellaria heterophylla , 1994 .

[21]  C. Chothia,et al.  Orthogonal packing of beta-pleated sheets in proteins. , 1982, Biochemistry.

[22]  James A. Ibers,et al.  International tables for X-ray crystallography , 1962 .

[23]  H. Morita,et al.  Conformational analysis of an antitumour cyclic pentapeptide, astin B, from Aster tataricus) , 1994 .

[24]  G. N. Ramachandran,et al.  Stereochemistry of polypeptide chain configurations. , 1963, Journal of molecular biology.

[25]  A M Lesk,et al.  Evolution of proteins formed by beta-sheets. II. The core of the immunoglobulin domains. , 1982, Journal of molecular biology.

[26]  P. L. Wessels,et al.  Conformational analysis of the cyclic peptide rhizonin a in solution and crystalline state , 1989 .

[27]  J. Ibers,et al.  Dispersion corrections and crystal structure refinements , 1964 .

[28]  U. Schmidt,et al.  The conformation of cyclo[l-pro-l-leu-l-val-(gly)thz-(gly)thz], a dolastatin 3 analog, in the crystalline and solution states , 1987 .

[29]  V. T. Ivanov,et al.  Refinement of the angular dependence of the peptide vicinal NHCαH coupling constant , 1973 .