Synthesis, crystal structure and molecular conformation of N α-Boc-L-leucyl-(Z)-β-(3-pyridyl)-α, β-dehydroalanyl-L-leucine methyl ester

Journal of Peptide Research

Volumn 65, Issue 2, 2005, Pages 167-174

  Yamada, K ^a   Oku, H ^a   Shinoda, S S ^a   Katakai, Ryoichi ^a  

^a GUNMA UNIVERSITY   (Japan)

Author keywords

(3 pyridyl) , dehydroalanine; Dehydropeptide; Extended conformation; X ray crystal structure

Indexed keywords

ALANINE DERIVATIVE; AMINO ACID; BETA (3 PYRIDYL) ALPHA,BETA DEHYDROALANINE; BETA PHENYL ALPHA,BETA DEHYDROALANINE; NALPHA TERT BUTOXYCARBONYLLEUCYL BETA (3 PYRIDYL) ALPHA,BETA DEHYDROALANYLLEUCINE O METHYL ESTER; SYNTHETIC PEPTIDE; TRIDEHYDROPEPTIDE; TRIPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; OLIGOPEPTIDES;

EID: 14744268565     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.2005.00232.x     Document Type: Article

References (32)

1. Mathur, P., Ramakumar, S. & Chauhan, V. S. (2004) Peptide design using α,β-dehydro amino acids: from β-turns to helical hairpins. Biopolymers (Pept. Sci.) 76, 150-161.
2. Inai, Y., Kurashima, S., Okado, Y., Hirabayashi, T. & Yokota, K. (1996) Conformational preference in β-aryldehydroalanine. Synthesis and conformational study of tripeptides containing β-aryldehydroalanine residues. Bull. Chem. Soc. Jpn 69, 1687-1694.
3. Inai, Y., Oshikawa, T., Yamashita, M., Hirabayashi, T. & Hirako, T. (2001) Structural and conformational properties of (Z)-β-(1-naphtyl)- dehydroalanine residue. Biopolymers 58, 9-19.
4. Inai, Y. & Hirabayashi, T. (2001) A helical arrangement of β-substituents of dehydropeptides: synthesis and conformational study of sequential nona- and dedecapeptides possessing (Z(-β-(1-naphthyl)- dehydroalanine residues. Biopolymers 59, 356-369.
5. Nakai, Y., Oku, H., Yamada, K. & Katakai, R. (2003) Structure and metal-binding properties of peptides containing β-(3-pyridyl)-L-alanine residues. In: Peptide Science 2002 (Yamada, T., ed.), pp. 313-316, The Japanese Peptide Society, Osaka.
6. Voskuyl-Holtkamp, I. & Schattenkerk, C. (1979) Studies on polypeptides. XXIX. Synthesis of the N-terminal tetradecapeptide sequence of ribonuclease A, incorporating β-(3-pyridyl)-L-alanine at position 12. Int. J. Pept. Protein Res. 13, 185-194.
7. Hoes, C., Kerling, K. E. T. & Havinga, E. (1983) Studies on polypeptides XXXIX. The role of the imidazole tele-nitrogen atom of histidine-12 in the catalytic action of RNase S'. Recl. Trav. Chim. Pays-Bas 102, 140-147.
8. Folkers, K., Bowers, C. Y., Kubiak, T. & Stepinski, J. (1983) Antagonists of the luteinizing hormone releasing hormone with pyridyl-alanines which completely inhibit ovulation at nanogram dosage. Biochem. Biophys. Res. Comm. 111, 1089-1095.
9. Shimeno, H., Fukumoto, Y., Fuji, M. & Nagamatsu, A. (1984) Comparative effects of DL, D and L-3-pyridylalanine on serotonin concentration and tryptophan-serotonin metabolizing enzymes. Chem. Pharm. Bull. 32, 3620-3625.
10. Rivier, J. E., Porter, J., Rivier, C. L., Perrin, M., Corrigan, A., Hook, W. A., Siraganian, R. P. & Vale, W. W. (1986) New effective gonadotropin releasing hormone antagonists with minimal potency for histamine release in vitro. J. Med. Chem. 29, 1846-1851.
11. Privett, H. K., Reedy, C. J., Kennedy, M. L. & Gibney, B. R. (2002) Nonnatural amino acid ligands in heme protein design. J. Am. Chem. Soc. 124, 6828-6829.
12. Inai, Y., Ito, T., Hirabayashi, T. & Yokota, K. (1993) Synthesis and conformational study of peptides possessing helically arranged Z-DehydroPhe side chains. Biopolymers 33, 1173-1184.
13. Glówka, M. L. (1988) Structure of a tripeptide containing a dehydro amino acid: tert-butoxycarbonylglycyl-dehydrophenylalanyl-glycine methyl ester. Acta Cryst. C44, 1639-1641.
14. 3. Biopolymers 26, 819-819.
15. 3. Int. J. Biol. Macromol. 19, 103-112.
16. 3. Int. J. Pept. Protein Res. 48, 123-128.
17. Walker, N. & Stuart, D. (1983) An empirical adsorption correction program. Acta Cryst. A39, 158-166.
18. Buria, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003) SIR2002: the program J. Appl. Cryst., 36, 1103.
19. Beurskens, P. T., Admiraal, G., Beurskens, G., Bosman, W. P., de Gelder, R., Israel, R. & Smits, J. M. M. (1999) The DIRDIF-99 program system, Technical report of the Crystallography Laboratory. University of Nijmegen, The Netherlands.
20. Farrugia, L. J. (1997) ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI). J. Appl. Cryst. 30, 565.
21. Cavelier, F. & Verducci, J. (1995) New synthesis of the cyclic tetrapeptide tentoxin employing an azlactone as key intermediate. Tetrahedron Lett. 36, 4425-4428.
22. 3. J. Mol. Struct. 658, 135-141.
23. 3. J. Pept. Res. 52, 89-94.
24. Vijayaraghavan, R., Makker, J., Kumar, P., Dey, S. & Singh, T. P. (2003) Design of peptides with α,β-dehydro-residues: syntheses, crystal structures and molecular conformations of two δ Phe-Trp containing peptides. J. Mol. Struct. 654, 103-110.
25. Fulton, N. D., Bollenbacher, K. & Templeton, G. E. (1965) A metabolite from Alternaria tennis that inhibits chlorophyll production. Phytopathology 55, 49-51.
26. Meyer, W. L., Templeton, G. E., Grable, C. T., Sigel, C. W. &. Jones, R. (1970) The structure of tentoxin. Tetrahedron Lett. 15, 2357-2360.
27. Rich, D. H., Bhatnagar, P., Mathiaparanam, B., Grant, J. A. & Tam, J. P. (1978) Synthesis of tentoxin and related dehydro cyclic tetrapeptides. J. Org. Chem. 43, 296-302.
28. Shimohigashi, Y., Stammer, C. H., Costa, T. &. Vonvoigtlander, P. F. (1983) Synthesis and biological activity of 4-dehydroPhe-enkephalins. Int. J. Pept. Protein Res. 11, 489-494.
29. Fisher, G. H., Ryan, J. W. & Berryer, P. (1983) Analogs of bradykinin containing dehydrophenylalanine. Adv. Exp. Med. Biol. 156A, 607-612.
30. Brady, S. F., Cochran, D. W., Nutt, R. F., Holly, F. W., Bennett, C. D., Paleveda, W. J., Curley, P. E., Arison, B. H., Saperstein, R. &. Veber, D. F. (1984) Synthesis and conformational study of a cyclic hexapeptide analog of somatostatin containing dehydrophenylalanine. Int. J. Pept. Protein Res. 13, 212-222.
31. Salvadori, S., Marastoni, M., Balboni, G., Marzola, G. & Tomatis, R. (1986) Dehydrodermorphins. I. Influence of the stereo-orientation of aromatic groups in dermorphin-(1-5)-peptides to opioid activity. Int. J. Pept. Protein Res. 28, 254-261.
32. Shimohigashi, Y., Kodama, H., Imazu, S., Horimoto, H., Sakaguchi, K., Waki, M., Uchida, H., Kondo, M., Kato, T. & Izumiya, N. (1987) [4,4′-(Z)-Dehydrophenylalanine]-gramicidin S with stabilized bioactive conformation and strong antimicrobial activity. FEBS Lett. 222, 251-255.