Synthesis of dermorphin-(1-4) derivatives catalyzed by proteases in organic solvents

Journal of Peptide Research

Volumn 65, Issue 1, 2005, Pages 143-148

  Shen, H Y ^a   Tian, Gui Ling ^a   Ye, Y H ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

D amino acid; Dermorphin; Organic solvents; Peptide synthesis; Proteases

Indexed keywords

CHYMOTRYPSIN A; DERMORPHIN DERIVATIVE; DERMORPHIN[1-4] DERIVATIVE; HEPTAPEPTIDE; ORGANIC SOLVENT; PROTEINASE; SUBTILISIN; TERT BUTYLOXYCARBONYLTYROSYL DEXTRO ALANYLPHENYLALANYLGLYCINAMIDE; TERT BUTYLOXYCARBONYLTYROSYL DEXTRO ALANYLPHENYLALANYLGLYCINE N PHENYLAMIDE; UNCLASSIFIED DRUG;

AMINO ACID COMPOSITION; AMINO ACID SEQUENCE; ANALGESIC ACTIVITY; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME MECHANISM; ENZYME SUBSTRATE; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHYMOTRYPSIN; MOLECULAR STRUCTURE; OLIGOPEPTIDES; OPIOID PEPTIDES; ORGANIC CHEMICALS; SOLVENTS; SUBTILISIN;

EID: 14044272100     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.2004.00198.x     Document Type: Article

References (28)

1. Bordusa, F. (2002) Proteases in organic synthesis. Chem. Rev. 102, 4817-4867.
2. Yan, A.-X., Tian, G.-L. & Ye, Y.-H. (2001) New developments on protease-catalyzed organic syntheses. Prog. Chem. 13, 203-208.
3. Margolin, A.L., Tai, D.-F. & Klibanov, A.M. (1987) Incorporation of D-amino acids into peptides via enzymatic condensation in organic solvents. J. Am. Chem. Soc. 109, 7885-7887.
4. Ricca, J.M. & Grout, D.H.G. (1989) Peptide synthesis catalyzed by chymotrypsin in organic solvents. J. Chem. Soc. Perkin Trans. 1, 2126-2127.
5. Thust, S. & Koksch, B. (2003) Protease-catalyzed peptide synthesis for the site-specific incorporation of α-fluoroalkyl amino acids into peptides. J. Org. Chem. 68, 2290-2296.
6. Wong, C-H., Schuster, M., Wang, P. & Sears, P. (1993) Enzymatic synthesis of N- and O-linked glycopeptides. J. Am. Chem. Soc. 115, 5893-5901.
7. Yang, H., Zhou, C., Tian, G.-L. & Ye, Y.-H. (2002) Enzymatic synthesis of dipeptide derivatives containing non-coded amino acids in organic solvents. Chin. J. Chem. 20, 1354-1357.
8. Miyazawa, T., Ensatsu, E., Yabuuchi, N., Yanagihara, R. & Yamada, T. (2002) Superiority of the carbamoylmethyl ester as an acyl donor for the kinetically controlled amide-bond formation mediated by α-chymotrypsin. J. Chem. Soc. Perkin Trans. 1, 390-395.
9. Ye, Y.-H. (1992) Enzymatic reactions in organic solvents. Univ. Chem. 7, 17-21.
10. Tian, G.-L., King, G.-W. & Ye, Y.-H. (1998) Some important problems of enzymatic reactions in non-aqueous media. Chin. J. Org. Chem. 18, 11-19.
11. Wong, C.-H. & Wang, K.-T. (1991) New developments in enzymatic peptide synthesis. Experientia 47, 1123-1129.
12. Shen, H.-Y., Tian, G.-L. & Ye, Y.-H. (2003) Recent progress in the study on enzymatic reactions in non-aqueous media. Chin. J. Org. Chem. 13, 221-229.
13. Yan, A.-X., Xing, G.-W., Ye, Y.-H., Tian, G.-L., Wong, M.-S. & Lee, K.-S. (2000) Studies of the enzymatic synthesis of N-protected amino acid-estradiol derivatives in an organic solvent. Tetrahedron Lett. 41, 5379-5381.
14. Liu, P., Tian, G.-L., Lo, W.-H., Lee, K.-S. & Ye, Y.-H. (2002) Synthesis of N-protected peptide alcohols catalyzed by subtilisin or α-chymotrypsin in organic solvents. Prep. Biochem. Biotechnol. 31, 29-37.
15. Xing, G.-W., Tian, G.-L. & Ye, Y.-H. (1998) Influence of reaction conditions on syntheses of sweetener precursors catalyzed by thermolysin in tert-amyl alcohol. J. Peptide Res. 51, 300-304.
16. Liu, P., Tian, G.-L., Lee, K.-S., Wong, M.-S. & Ye, Y.-H. (2002) Full enzymatic synthesis of a precursor of bioactive pentapeptide OGP (10-14) in organic solvents. Tetrahedron Lett. 43, 2423-2425.
17. Liu, P., Ye, Y.-H., Tian, G.-L., Lee, K.-S., Wong, M.-S. & Lo, W.-H. (2002) Synthesis of a precursor of bioactive pentapeptide OGP-(10-14) and the fragment of enkephalin catalyzed by MCM-22 immobilized or free proteases in organic solvents. Synthesis, 726-732.
18. Filippova, I.Y. & Lysogorskaya, E.N. (2003) Modified proteases for peptide synthesis in organic media. Russ. J. Bioorg. Chem. 19, 496-501.
19. Xiang, H., Xiang, G.Y., Lu, Z.M., Guo, L. & Eckstein, H. (2004) Total enzymatic synthesis of cholecystokinin CCK-5. Amino Acids 17, 101-105.
20. Broccardo, M., Erspamer, V., Falconieri-Erspamer, G., Improta, G., Linari, G., Melchiorri, P. & Montecucchi, P.C. (1981) Pharmacological data on dermorphins, a new class of potent opioid peptides from amphibian skin. Br. J. Pharmacol. 73, 625-631.
21. Montecucchi, P.C., de Castiglione, R., Piani, S., Gozzini, L. & Erspamer, V. (1981) Amino acid composition and sequence of dermorphin, a novel opiate-like peptide from the skin of Phyllomedusa sauvagei. Int. J. Peptide Protein Res. 17, 275-283.
22. 6-dermorphin in skin extracts of the Brazilian frog Phyllomedusa rhodei. Int. J. Peptide Protein Res. 17, 316-321.
23. Kullmann, W. (1983) Protease-catalyzed synthesis of melanocyte- stimulating hormone (MSH) fragments. J. Protein Chem. 2, 289-301.
24. Salvadori, S., Sarto, G. & Tomatis, R. (1982) Synthesis and pharmacological activity of dermorphin and its N-terminal sequences. Int. J. Peptide Protein Res. 19, 536-542.
25. Zhou, C., Tian, G.-L., Shen, H.-Y. & Ye, Y.-H. (2001) Effect of salt hydrates on enzymatic oligopeptide synthesis in organic solvents. Acta Chim. Sinica 59, 1707-1711.
26. Kvittingen, L., Sjursnes, B., Anthonsen, T. & Halling, P. (1992) Use of salt hydrates to buffer optimal water level during lipase catalysed synthesis in organic media: a practical procedure for organic chemists. Tetrahedron 48, 2793-2802.
27. Sakina, K., Kawazura, K. & Morihara, K. (1988) Enzymatic synthesis of delta sleep-inducing peptide. Int. J. Peptide Protein Res. 31, 245-252.
28. Shen, H.-Y., Tian, G.-L., Yan, A.-X., Jia, Y., Hong, Y.-Y. & Ye, Y.-H. (2003) Effect of the properties of organic solvents and water content on the enzymatic synthesis of derivatives of dipeptides containing D-amino acid residue. Acta Chim. Sinica 61, 1144-1148.