Solvolysis and aminolysis on peptidyl-Kaiser oxime resin assisted by Ca2+ and Eu3+: A mild procedure to prepare α-methyl and -ethyl esters of protected peptides

Journal of Peptide Research

Volumn 55, Issue 4, 2000, Pages 279-288

  Moraes, C M ^a   Bemquerer, M P ^b   Miranda, M Teresa M ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

Aminolysis; Calcium; Ethanolysis; Europium III; Methanolysis; Peptidyl Kaiser oxime resin; Protected peptide esters

Indexed keywords

ACETIC ACID; CALCIUM ION; ESTER; EUROPIUM; OXIME; RESIN;

ARTICLE; ESTERIFICATION; PRIORITY JOURNAL; PROTEIN DEGRADATION; REACTION ANALYSIS;

CALCIUM; CHEMISTRY, PHYSICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERS; ETHANOL; EUROPIUM; HYDROLYSIS; METHANOL; OXIMES; PEPTIDES; RESINS, PLANT;

EID: 0034072407     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2000.00173.x     Document Type: Article

References (33)

1. 1. Jakubke, H.D. (1994) Protease catalyzed peptide synthesis - basic principles, new synthesis strategies and medium engineering. J. Chin. Chem. Soc. 41, 355-370.
2. 2. Bemquerer, M.P., Liria, C.W., Kitagawa, K., Faljoni-Alario, A., Miranda, M.T.M. & Tominaga, M. (1998) Enzymatic peptide fragment condensation: structural studies of trypsin in mixtures of trifluoroethanol and dimethylformamide. In Peptides 1996, Proceeding of the 24th European Peptide Symposium (Ramage, R. & Epton, R., eds). Mayflower Scientific Ltd, Kingswinford, UK, pp. 251-252.
3. 3. Bemquerer, M.P., Liria, C.W., Kitagawa, K., Miranda, M.T.M. & Tominaga, M. (1998) Mixtures of trifluoroethanol or hexafluoroisopropanol and dimethylformamide are not of general applicability for peptide condensations catalyzed by trypsin. J. Peptide Res. 51, 29-37.
4. 4. Gololobov, M.Y., Kozlova, E.V., Borisov, I.L., Schellenberger, U., Schellenberger, V. & Jakubke, H.-J. (1992) How to predict product yield in kinetically controlled enzymatic peptide synthesis. Biotechnol. Bioeng. 40, 432-436.
5. 5. Bongers, J. & Heimer, E.P. (1994) Recent applications of enzymatic peptide. Peptides 15, 183-193.
6. 6. Capellas, M., Caminal, G., Gonzalez, G., López-Santín, J. & Clapés, P. (1997) Enzymatic condensation of cholecystokinin CCK-8 (4-6) and CCK-8 (7-8) peptide fragments in organic media. Biotechnol. Bioeng. 56, 456-463.
7. 7. Schellenberger, V., Turck, C.W. & Rutter, W.J. (1994) Role of the S′ subsites in serine-proteases catalysis-active-site mapping of rat chymotrypsin, rat trypsin, alpha-lytic protease, and cerearial protease from Schistosoma mansoni. Biochemistry 33, 4251-4257.
8. 8. Bodanszky, M. (1993) Peptide Chemistry - A Practical Textbook, 2nd edn. Springer-Verlag, Heidelberg.
9. 9. Noritomi, H., Watanabe, A. & Kise, H. (1989) Enzymatic reactions in aqueous organic media.7. Peptide and ester synthesis in organic solvents by alpha-chymotrypsin immobilized through non covalent binding to poly(vinyl-alcohol). Polymer J. 21, 147-153.
10. 10. Kim, M.H. & Patel, D.V. (1994) BOP as a reagent for mild and efficient preparation of esteres. Tetrahedron Lett. 35, 5603-5606.
11. 11. Seebach, D., Thaler, A., Blaser, D. & Soo, Y.K. (1991) Transesterifications with 1,8 diazabicyclo(5.4.0)undec-7-ene/lithium bromide (DBU/LiBr.) - also applicable to cleavage of peptides from resins in Merrifield syntheses. Helv. Chim. Acta 74, 1102-1118.
12. 12. Siemens, L.M., Rottneck, F.W. & Trzupek, L.S. (1990) Selective catalysis of ester aminolysis - an approach to peptide active esters. J. Org. Chem. 55, 3507-3511.
13. 13. DeGrado, W.F. & Kaiser, E.T. (1980) Polymer-bound oxime esters as supports for solid-phase peptide-synthesis - preparation of protected peptide-fragments. J. Org. Chem. 45, 1295-1300.
14. 14. DeGrado, W.F. & Kaiser, E.T. (1982) Solid-phase synthesis of protected peptides on a polymer-bound oxime - preparation of segments comprising the sequence of acytotoxic 26-peptide analog. J. Org. Chem. 47, 3258-3261.
15. 15. Pichette, A., Voyer, N., Larouche, R. & Meillon, J.-C. (1997) A useful method for the preparation of fully protected peptide acids and esters. Tetrahedron Lett. 38, 1279-1282.
16. 16. Hendrix, J.C., Jarret, J.T., Anisfeld, S.T. & Lansbury, P.T. Jr (1992) Studies related to a convergent fragment-coupling approach to peptide - synthesis using the Kaiser oxime resin. J. Org. Chem. 57, 3414-3420.
17. 17. Hamuro, Y., Scialdone, M.A. & DeGrado, W. (1999) Resin-to-resin and aminoacyl-transfer reactions using oxime supports. J. Am. Chem. Soc. 121, 1636-1644.
18. 2+ mediated catalysis. Int. J. Peptide Protein Res. 37, 299-305.
19. 19. Miranda, M.T.M., Theobaldo, F.C. & Tominaga, M. (1991) Transesterification of peptide esters and peptidyl resins in methanol-containing calcium acetate. Int. J. Peptide Protein Res. 37, 451-456.
20. 20. Moraes, C.M., Bemquerer, M.P. & Miranda, M.T.M. (1997). Poster Presented at the 15th American Peptide Symposium, June 1997, Nashville, TN, p. 150.
21. 3+. In Peptides 1998, Proceedings of the 25th European Peptide Symposium (Bajusz, S. & Hudecz, F., eds). Akadémiai Kiadó, Budapest, Hungary, pp. 230-231.
22. 22. Smillie, L.B. & Nattriss, M. (1991) Amino acid analyses of proteins and peptides: an overview. In High Performace Liquid Chromatography of Peptides and Proteins -Separation, Analysis and Conformation (Mant, C.T. & Hodges, R.S., eds). CRC Press, Boca Raton, FL, pp. 847-863.
23. 23. Stewart, J.M. & Young, J. (1984). Solid Phase Peptide Synthesis, 2nd edn. Pierce Chemical Co., Rockford, IL.
24. 24. Gisin, B.F. (1972) The monitoring of reactions in solid-phase peptide synthesis with picric acid. Anal. Chim. Acta. 58, 248-249.
25. 25. Kaiser, E., Colescott, R.L., Bossinger, C.D. & Cook, P.I. (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 34, 595-598.
26. 26. Crawley, J.N. & Corwin, R.L. (1994) Biological actions of cholecystokinin. Peptides 15, 731-755.
27. 27. Liria, C.W., Bemquerer, M.P. & Miranda, M.T.M. (1998) Premature removal of N-alpha-9-fluorenylmethyloxycarbonyl in thermodynamically controlled enzymatic coupling trials. Tetrahedron Lett. 39, 4207-4210.
28. 28. Nishino, N., Xu, M., Mihara, H., Fujimoto, T., Ueno, Y. & Kumagai, H. (1992) Sequence dependence in solid-phase-synthesis-cyclization-cleavage for cyclo (-arginyl-glycyl-aspartyl-phenylglycyl-). Tetrahedron Lett. 33, 1479-1481.
29. 29. Mihara, H., Yamabe, S., Niidome, T. & Aoyagi, H. (1995) Efficient preparation of cyclic peptide mixtures by solid-phase synthesis and cyclization cleavage with oxime resin. Tetrahedron Lett. 36, 4837-4840.
30. 30. Richardson, F.S. (1982) Terbium (III) and europium (III) ions as luminescent probes and stains for biomolecular systems. Chem. Rev. 82, 541-552.
31. 31. Elbanowski, M. & Makowska, B. (1996) The lanthanides as luminescent probes in investigations of biochemical systems. J. Photochem. Photobiol. A: Chem. 99, 85-92.
32. 32. Takarada, T., Takahashi, R., Yashiro, M. & Komiyama, M. (1998) Lanthanide ion-induced hydrolyses of alkyl esters and amides of alpha-amino acids. J. Phys. Org. Chem. 11, 41-46.
33. 33. Fukuzawa, S.-I. & Hongo, Y. (1998) Transesterification of N-acyloxazolidinones with alcohol by lanthanum (III) iodide. Tetrahedron Lett. 39, 3521-3524.