Conformational studies of vasopressin analogues modified with N-methylphenylalanine enantiomers in dimethyl sulfoxide solution

Biopolymers

Volumn 82, Issue 6, 2006, Pages 603-614

  Sikorska, Emilia ^a   Ślusarz, Magdalena J ^a   Lammek, Bernard ^a  

^a UNIVERSITY OF GDA SK   (Poland)

Author keywords

Dimethyl sulfoxide; N methylphenylalanine enantiomers; Vasopressin

Indexed keywords

CATALYST SELECTIVITY; CHEMICAL BONDS; CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLVENTS;

DIMETHYL SULFOXIDE; N-METHYLPHENYLALANINE ENANTIOMERS; OXYTOCIN (OT); VASOPRESSIN;

ISOMERS;

DIMETHYL SULFOXIDE; SOLVENT; UTEROTONIC AGENT; VASOPRESSIN DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; CORRELATION COEFFICIENT; ENANTIOMER; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SPECTROSCOPY;

AMINO ACID SEQUENCE; ARGININE VASOPRESSIN; BIOPOLYMERS; DIMETHYL SULFOXIDE; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHENYLALANINE; PROTEIN CONFORMATION; SOLUTIONS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33746955154     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.20514     Document Type: Article

References (43)

1. Rascher, W.; Lang, R. E.; Unger, T. In Neurobiology of Vasopressin; Ganten, D., Pfaff, D., Eds.; Springer Verlag: Berlin-Heidelberg, 1985; pp 101-136.
2. Trasher, T. N. Front Neuroendocrinol 1994, 15, 157-196.
3. Hlavacek, J. In Handbook of Neurohypophyseal Hormone Analogs; Jost, K., Lebl, M., Brtnik, F., Eds.; CRC Press: Boca Raton, FL, 1987; pp 109-129.
4. Manning, M.; Sawyer, W. H. J Lab Clin Med 1989, 114, 617-632.
5. Manning, M.; Stoev, S.; Chan, W. Y.; Sawyer, W. H. Ann NY Acad Sci 1993, 689, 219-232.
6. Dorman, D. E.; Bovey, F. A. J Org Chem 1973, 38, 2379-2383.
7. Higashijima, T.; Tasumi, M.; Miyazawa, T. Biopolymers 1977, 16, 1259-1270.
8. Ishimoto, B.; Tonan, K.; Ikawa, S. Spectrochim Acta Part A 1999, 56, 201-209.
9. Sikorska, E.; Ślusarz, M. J.; Ślusarz, R.; Kowalczyk, W.; Lammek, B. J Pept Sci 2006, 12, 13-24.
10. Vitoux, B.; Aubry, A.; Cung, M. T.; Marrad, M. J Pept Protein Res 1986, 27, 617-632.
11. Kowalczyk, W.; Derdowska, I.; Dawidowska, O.; Prahl, A.; Hartrodt, B.; Neubert, K.; Slaninova, J.; Lammek, B. J Pept Res 2003, 63, 420-425.
12. Bax, A.; Davis, D. G. J Magn Reson 1985, 65, 355-360.
13. Braunschweiler, L.; Ernst, R. R. J Magn Reson 1983, 53, 521-528.
14. Bax, A.; Davis, D. G. J Magn Reson 1985, 63, 207-213.
15. Palmer, A. G., III; Cavanagh, J.; Wright, P. E.; Rance, M. J Magn Reson 1991, 93, 151-170.
16. Kay, L. E.; Keifer, P.; Saarinen, T. J Am Chem Soc 1992, 114, 10663-10665.
17. Kontaxis, G.; Stonehouse, J.; Laue, E. D.; Keeler, J. J Magn Reson Ser A 1994, 111, 70-76.
18. Bax, A.; Summers, M. F. J Am Chem Soc 1986, 108, 2093-2094.
19. Delaglio, F.; Grzesiek, S.; Geerten, W. V.; Zhu, G.; Pfeifer, J.; Bax, A. J Biomol NMR 1995, 6, 277-293.
20. Bartles, C.; Xia, T.; Billeter, M.; Günter, P.; Wütrich, K. J Biomol NMR 1995, 5, 1-10.
21. Hoffman, R. E.; Davies, D. B. Magn Reson Chem 1988, 26, 523-525.
22. Kozminski, W. J Magn Reson 1998, 134, 189-193.
23. Ripoll, D. R.; Scheraga, H. A. Biopolymers 1988, 27, 1283-1303.
24. Némethy, G.; Gibson, K. D.; Palmer, K. A.; Yoon, C. N.; Paterlini, G.; Zagari, A.; Rumsey, S.; Scheraga, H. A. J Phys Chem 1992, 96, 472-484.
25. Vila, J.; Williams, R. L.; Vasquez, M.; Scheraga, H. A. Protein Struct Funct Genet 1991, 10, 199-218.
26. Späth, H. Cluster Analysis Algorithms; Halsted Press: New York, 1980; pp 170-194.
27. Meadows, R. P.; Post, C. B.; Luxon, B. A.; Gorenstein, D. G. MORASS 2.1, Purdue University, West Lafayette, IN, 1994.
28. Post, C. B.; Meadows, R. P.; Gorenstein, D. G. J Am Chem Soc 1990, 112, 6796-6803.
29. Massefski, W., Jr.; Bolton, P. H. J Magn Reson 1985, 65, 526-530.
30. Yu, C.; Yang, T. H.; Yeh, C. J.; Chuang, L. C. Can J Chem 1992, 70, 1950-1955.
31. Bystrov, V. F. Progr NMR Spectrosc 1976, 10, 41-81.
32. Dyson, H. J.; Rance, M.; Houghten, R. A.; Lerner, R. A.; Wright, P. E. J Mol Biol 1988, 201, 161-200.
33. Lewis, P. N.; Mamony, F. A.; Scheraga, H. A. Biochem Biophys Acta 1973, 303, 211-229.
34. McDonald, I. K.; Thornton, J. M. J Mol Biol 1994, 238, 777-793.
35. Koradi, R.; Billeter, M.; Wüthrich, K. J Mol Graphics 1996, 14, 52-55.
36. Schmidt, J. M.; Ohlenschläger, O.; Rüterjans, H.; Grzonka, Z.; Kojro, E.; Pavo, I.; Farenholz, F. Eur J Biochem 1991, 204, 355-371.
37. Walse, B.; Kihlberg, J.; Drakenberg T. Eur J Biochem 1998, 252, 428-440.
38. Trzepalka, E.; Kowalczyk, W.; Lammek, B. J Pept Res 2004, 63, 333-346.
39. Slusarz, M. J.; Sikorska, E.; S̀lusarz, R.; Ciarkowski, J. J Med Chem 2006, 49, 2463-2469.
40. Sikorska, E.; S̀lusarz, R.; Lammek, B. J Pept Res 2006, 44(Suppl. 1), 30-40.
41. Langs, D. A.; Smith, G. D.; Stezowski, J. J.; Hughes, R. E. Science 1986, 232, 1240-1242.
42. Kaźmierkiewicz, R.; Czaplewski, C.; Lammek, B.; Ciarkowski, J. J Comput-Aided Mol 1997, 11, 9-20.
43. Wang, J.; Hodges, R.S.; Sykes, B.D. Int J Pept Protein Res 1995, 45, 471-481.