H and 13C nuclear magnetic resonance spectra of some peptides with fibrinogen-like reactivity

International Journal of Peptide and Protein Research
I D Rae, H A Scheraga

Abstract

The 1H and 13C spectra of four peptides, L-Phe-Val-Arg-pNA, D-Phe-Val-Arg-pNA, L-Phe-Pip-Arg-pNA and D-Phe-Pip-Arg-pNA (pNA = p-nitroaniline, Pip = pipecolic acid residue), have been examined, and deductions made about their conformation in solution. The D-Phe peptides, which are cleaved especially rapidly by thrombin in water, have structures (in deuterated DMSO) in which the aromatic ring of the D-Phe residue is folded back over the Val or Pip residue. This arrangement is not found in the L-Phe peptides. It is proposed that this feature (in which Phe could be situated near Val and near the Arg-Gly bond of the A alpha chain in the three-dimensional structure of fibrinogen) may be especially advantageous for binding to the enzyme.

References

May 1, 1976·Thrombosis Research·B BlombäckB Kudryk
Dec 8, 1972·Annals of the New York Academy of Sciences·B Blombäck, M Blombäck
Jan 1, 1972·Biopolymers·C M Deber, H Joshua
Nov 1, 1970·Tetrahedron·W LijinskyJ Loo

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Citations

Jun 27, 1983·Annals of the New York Academy of Sciences·H A Scheraga
Dec 2, 2004·Biophysical Chemistry·Julie E Scheffler, Lawrence J Berliner

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