Cis/trans conformational equilibrium across the N-methylphenylalanine 2-N-methylphenylalanine3 peptide bond of arginine vasopressin analogs

Journal of Peptide Research

Volumn 63, Issue 4, 2004, Pages 333-346

  Trzepalka E ^a   Kowalczyk, W ^a   Lammek, B ^a  

^a UNIVERSITY OF GDA SK   (Poland)

Author keywords

Analogs of vasopressin; cis trans isomerization; Conformational studies; N methylation; NMR spectroscopy; X PLOR

Indexed keywords

AMINO ACID DERIVATIVE; ARGININE DERIVATIVE; CYSTEINE DERIVATIVE; CYSTEINE DEXTRO METHYLPHENYLALANINE DEXTRO METHYLPHENYLALANYLGLYCYLASPARAGINYLCYSTEINYLPROLYLGLYCINAMIDE; CYSTEINYLMETHYLPHENYLALANYLMETHYLPHENYLALANYLGLUTAMINYLASPARAGINYLCYSTEINYL PROLYLARGINYLGLYCINAMIDE; DEUTERIUM; NITROGEN DERIVATIVE; OXYGEN DERIVATIVE; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG; VASOPRESSIN DERIVATIVE; WATER;

ALGORITHM; AQUEOUS SOLUTION; ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CIS TRANS ISOMERISM; CONFORMATIONAL TRANSITION; CORRELATION ANALYSIS; CYCLIZATION; DENSITY GRADIENT CENTRIFUGATION; GEOMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SIMULATION; SOLID; SPECTROSCOPY; STRUCTURE ANALYSIS; TECHNIQUE;

ARGININE VASOPRESSIN; HYDROGEN BONDING; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PEPTIDES, CYCLIC; PHENYLALANINE;

EID: 2442572183     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.2004.00103.x     Document Type: Article

References (52)

1. Rittig, S., Robertson, G.L., Siggaard, C., Kovacs, L., Gregersen, N., Nyborg, J. & Pederson, E.B. (1996) Identification of 13 new mutations in the vasopressin-neurophysin II gene in 17 kindreds with familial autosomal dominant neurohypophyseal diabetes insipidus. Am. J. Hum. Genet. 58, 107-117.
2. Gainer, H. (1998) Cell-specific gene expression in oxytocin and vasopressin magnocellular neurons. Adv. Exp. Med. Biol. 449, 15-17.
3. Dichter, D. (1985) Biosynthesis of vasopressin. In: Neurobiology of Vasopressin (Ganten, D. & Pfaff, D., eds), pp. 1-16. Springer-Verlag, New York.
4. Schmidt, J.M., Ohlenschläger, O., Rüterjans, H., Grzonka, Z., Kojro, E., Pavo, I. & Fahrenholz, F. (1991) Conformation of [8-arginine]vasopressin and V1 antagonists in dimethyl sulfoxide solution derived from two-dimensional NMR spectroscopy and molecular dynamics simulation. Eur. J. Biochem. 201, 355-371.
5. Mouillac, B., Chini, B., Nalestre, M.N., Elands, J., Trumpp-Kallmeyer, S., Hoflack, J., Hibert, M., Jard, S. & Barberis, C. (1995) The binding site of neuropeptide vasopressin Via receptor. Evidence for a major localization within transmembrane regions. J. Biol. Chem. 270, 25771-25777.
6. Hlavacek, J. (1987) Important structural modifications. Noncoded amino acid. In: Handbook of Neurohypophyseal Hormone Analogs, Vol. 1. Part 2 (Jošt, K., Lebl, M., Brtnik, F., eds), pp. 109-129. CRC Press Inc., Boca Raton, FL.
7. Reissmann, S., Schwuchow, C., Seyfarth, L., Pineda de Castro, L.F., Liebemann, C., Paegelow, I., Werner, H. & Stewart, J.M. (1996) Highly selective bradykinin agonists and antagonists with replacement of proline residues by N-methyl-D- and L-phenylalanine. J. Med. Chem. 39, 929-936.
8. Vitoux, B., Aubry, A., Cung, M.T. & Marrad, M. (1986) N-Methyl peptides. VII. Conformational perturbations induced by N-methylation of model dipeptides. J. Pept. Protein Res. 27, 617-632.
9. Wang, S.S. (1973) p-alkoxybenzyl alcohol resin and p-alkoxybenzyloxy- carbonylhydrazide resin for solid phase synthesis of protected peptide fragments. J. Am. Chem. Soc. 95, 1328-1333.
10. Braunschweiler, L. & Ernst, R.R. (1983) Coherence transfer by isotropic mixing: Application to correlation spectroscopy. J. Magn. Reson. 53, 521-528.
11. Bax, A. & Freeman, R. (1985) Enhanced NMR resolution by restricting the effective sample volume. J. Magn. Reson. 65, 355-360.
12. Bax, A. & Davis, D.G. (1985) Practical aspects of two-dimensional transverse NOE spectroscopy. J. Magn. Reson. 63, 207-213.
13. Kay, L.E., Keifer, P. & Saarinen, T. (1992) Pure absorption gradient enhanced heteronuclear single quantum correlation spectroscopy with improved sensitivity. J. Am. Chem. Soc. 114, 10663-10665.
14. Palmer, A.G. III, Cavanagh, J., Wright, P.E. & Rance, M. (1991) Sensitivity improvement in proton-detected two dimensional heteronuclear correlation NMR spectroscopy. J. Magn. Reson. 93, 151-170.
15. Kontaxis, G., Stonehouse, J., Laue, E.D. & Keeler, J. (1994) The sensitivity of experiments which use gradient pulses for coherence-pathway selection. J. Magn. Reson. Ser. A 111, 70-76.
16. Bax, A. & Summers, M.F. (1986) HMBC = Heteronuclear multiple-bond correlation. J. Am. Chem. Soc. 108, 2093-2094.
17. Delaglio, F., Grzesiek, S., Geerten, W.V., Zhu, G., Pfeifer, J. & Bax, A. (1995) NMRPipe: a multidimensional spectral processing system based on UNIX pipes. J. Biomol. NMR 6, 277-293.
18. Bartles, C., Xia, T., Billeter, M., Günter, P. & Wütrich, K. (1995) The program XEASY for the computer-supported NMR spectral analysis of biological macromolecules. J. Biomol. NMR 5, 1-10.
19. Gottlieb, H.E., Kotlyar, V. & Nudelman, A. (1997) NMR chemical shifts of common laboratory solvents as trace impurities. J. Org. Chem. 62, 7512-7515.
20. Wishart, D.S., Bigam, C.G., Holm, A., Hogdes, R.S. & Sykes, B.D. (1995) 1H/ 13C and 15N random coil NMR chemical shifts of the common amino acids. I. Investigations of nearest-neighbor effects. J. Biomol. NMR 5, 67-81.
21. Koźminski, W. (1998) The new active-coupling-pattern tilting experiment for an efficient and accurate determination of homonuclear coupling constants. J. Magn. Reson. 134, 189-193.
22. Wüthrich, K., Billeter, M. & Braun, W. (1983) Pseudo-structures for the 20 common amino acids for use in studies of protein conformations by measurements of intramolecular proton-proton distance constraints with nuclear magnetic resonance. J. Mol. Biol. 169, 949-961.
23. Güntert, P., Braun, W. & Wüthrich, K. (1991) Efficient computation of three-dimensional structures in solution from nuclear magnetic resonance data using the program DIANA and the supporting programs CALIBA, HABAS and GLOMSA. J. Mol. Biol. 217, 517-530.
24. Güntert, P. & Wüthrich, K. (1991) Improved efficiency of protein structure calculation NMR data using program DIANA with redundant dihedral angle constraints. J. Biomol. NMR 1, 447-456.
25. Bystrov, V.F. (1976) Spin-spin coupling and the conformational states of peptide systems. Progr. NMR Spectrosc. 10, 41-81.
26. Brünger, A.T. (1993) The X-PLOR Software Manual, Version 3.1. Yale University Press, New Haven, CT.
27. Brooks, B., Bruccoleri, R., Olafson, B.O., States, D.J., Swaminathan, S. & Karplus, M. (1993) CHARMM: a program for macromolecular energy, minimization and dynamics calculations. J. Comp. Chem. 4, 187-217.
28. Lewis, P.N., Mamony, F.A. & Sheraga, H.A. (1973) Chain reversals in proteins. Biochem. Biophys. Acta 303, 211-229.
29. McDonald, I.K. & Thornton, J.M. (1994) Satisfying hydrogen bonding potential in proteins. J. Mol. Biol. 238, 777-793.
30. Koradi, R., Billeter, M. & Wüthrich, K. (1996) MOLMOL: a program for display and analysis of macromolecular structures. J. Mol. Graphics 14, 52-55.
31. Dyson, H.J., Rance, M., Hoighten, R.A., Lerner, R.A. & Wright, P.E. (1988) Folding of immunogenic peptide fragments of proteins in water solution. I. Sequence requirements for the formation of a reverse turn. J. Mol. Biol. 201, 161-200.
32. Ohnishi, M. & Urry, D. W. (1969) Temperature dependence of amide proton chemical shifts: the secondary structures of gramicidin S and valinomycin. Biochem. Biophys. Res. Commun. 36, 194-202.
33. Eberstadt, M., Gemmecker, G., Mierke, D.F. & Kessler, H. (1995) Skalare Kopplungen - ihre Analyse und ihre Verwendung zur Strukturaufklä rung. Angew. Chem. Int. Ed. Engl. 34, 1671-1695.
34. Smith, L.J., Bolin, K.A., Schwalbe, H., MacArthur, M.W., Thornton, J.M. & Dobson, C.M. (1996) Analysis of main chain torsion angles in proteins: prediction of NMR coupling constants for native and random coil conformations. J. Mol. Biol. 255, 494-506.
35. Walse, B., Kihlberg, J. & Drakenberg, B. (1998) Conformation of desmopressin, an analogue of the peptide hormone vasopressin, in aqueous solution as determined by NMR spectroscopy. Eur. J. Biochem. 252, 428-440.
36. Lammek, B., Czaja, M., Derdowska, I., Łempicka, E., Sikora, P., Szkrøbka, W. & Trzeciak, H.I. (1998) Biologically active analogues of arginine vasopressin containing conformationally restricted dipeptide fragments. J. Peptide Res. 51, 149-154.
37. Walter, P. (1977) Identification of sites in oxytocin involved in uterine receptor recognition and activation. Fed. Proc. 36, 1872-1878.
38. Hempel, J.C. (1987) The conformation of neurohypophyseal hormones. In: The Peptides: Analysis, Synthesis, Biology, Vol. 8 (Smith, C.W., ed.), pp. 209-237. Academic Press, New York.
39. Hruby, V.J. & Lebl, M.I. (1987) Conformational properties of neurohypophyseal hormone analogs in solution as determined by NMR and laser RAMAN spectroscopies. In: CRC Handbook of Neurohypophyseal Hormone Analogs, Vol. 1 (Jost, K., Lebl, M., Brtnik, F., eds), pp. 105-155. CRC Press, Boca Raton, FL.
40. Liwo, A., Tempczyk, A., Oldziej, S., Shenderovich, M.D., Hruby, V.J., Talluri, S., Ciarkowski, J., Kasprzykowski, F., Łankiewicz, L. & Grzonka, Z. (1995) Exploration of the conformational space of oxytocin and arginine-vasopressin using the electrostatically driven Monte Carlo and molecular dynamics methods. Biopolymers 38, 157-175.
41. Kaźmierkiewicz, R., Czaplewski, C., Lammek, B. & Ciarkowski, J. (1997) Molecular modeling of the neurophysin I/oxytocin complex. J. Comput. Aided Mol. Des. 11, 9-20.
42. Langs, D.A., Smith, G.D., Stezowski, J.J. & Hughes, R.E. (1986) Structure of pressinoic acid: the cyclic moiety of vasopressin. Science 232, 1240-1242.
43. 8] vasopressin by 1H-NMR spectroscopy and molecular mechanics calculations. Int. J. Pept. Protein Res. 38, 528-538.
44. Yu, C., Yang, T.H., Yeh, C.J. & Chuang, L.C. (1992) Combined use of NMR, distance geometry, and restrained energy minimization for the conformational analysis of 8-lysine-vasopressin. Can. J. Chem. 70, 1950-1955.
45. 8]vasopressin methylenedithioether in dimethylsulfoxide using NMR. Eur. J. Biochem. 267, 4504-4510.
46. Wang, J., Hodges, R.S. & Sykes, B.D. (1995) Effect of trifluoroethanol on the solution structure and flexibility of desmopressin: a two-dimensional NMR study. Int. J. Pept. Protein Res. 45, 471-481.
47. 7)desamino- vasopressin analogues using NMR spectroscopy. J. Pept. Sci. 8, 347-364.
48. Kaźmierkiewicz, R., Liwo, A. & Lammek, B. (1995) Theoretical conformational analysis of three vasopressin antagonists with a modified cyclohexyl ring in the first thioacid residue. Int. J. Pept. Protein Res. 45, 451-458.
49. Ślusarz, R., Kaźmierkiewicz, R. & Lammek, B. (2000) Theoretical conformational analysis of six arginine vasopressin analogs with the L-naphthylalanine in position 3. J. Pept. Res. 56, 352-359.
50. Grzonka, Z., Mishra, P.K. & Bothner-By, A.A. (1985) Conformational preferences and binding to neurophysins of oxytocin analogs with sarcosine or N-methylalanine in position 7. J. Pept. Protein Res. 25, 375-381.
51. 6-proline peptide bond of oxytocin, arginine vasopressin, and lysine vasopressin. J. Am. Chem. Soc. 114, 7331-7337.
52. Grathwohl, C. & Wüthrich, K. (1976) The X-Pro peptide bond as an NMR probe for conformational studies of flexible linear peptides. Biopolymers 15, 2025-2041.