Utilization of proteases from Aspergillus species for peptide synthesis via the kinetically controlled approach

Biocatalysis and Biotransformation

Volumn 21, Issue 3, 2003, Pages 93-100

  Miyazawa, Toshifumi ^a   Hiramatsu, Makoto ^a   Murashima, Takashi ^a   Yamada, Takashi ^a  

^a KONAN UNIVERSITY   (Japan)

Author keywords

1,1,1,3,3,3 Hexafluoro 2 propanol DMF; Aspergillus melleus protease; Aspergillus oryzae protease; Carbamoylmethyl ester; Enzymatic peptide synthesis; Kinetically controlled approach; Microbial proteases

Indexed keywords

ACETONITRILE; AMINO ACIDS; BIOSYNTHESIS; CATALYSIS; CHEMICAL BONDS; CONDENSATION; REACTION KINETICS; SOLVENTS;

ASPERGILLUS SPECIES;

PROTEINS;

ACETONITRILE; AMINO ACID; BACTERIAL ENZYME; CARBAMOYLMETHYL ESTER; CARBOXYL GROUP; CHYMOTRYPSIN A; ESTER; HEXAFLUORO 2 PROPANOL; N,N DIMETHYLFORMAMIDE; PEPTIDE; PROTEINASE; UNCLASSIFIED DRUG; WATER;

ARTICLE; ASPERGILLUS; BACTERIAL KINETICS; CATALYST; CONTROLLED STUDY; COUPLING FACTOR; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PEPTIDE SYNTHESIS;

ASPERGILLUS; ASPERGILLUS MELLEUS; ASPERGILLUS ORYZAE; BACTERIA (MICROORGANISMS);

EID: 0141887076     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.1080/1024242031000108831     Document Type: Article

References (25)

1. Björup, P., Torres, J.L., Adlercreutz, P. and Clapés, P. (1998) "Reaction medium engineering in enzymatic peptide fragment condensation: Synthesis of eledoisin and LH-RH", Bioorg. Med. Chem. 6, 891-901.
2. Capellas, M., Caminal, G., Gonzalez, G., López-Santin, J. and 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.
3. Čeřovsky, V. and Jakubke, H.-D. (1996) "Nucleophilic specificity of subtilisin in an organic solvent with low water content: Investigation via acyl transfer reactions", Biotechnol. Bioeng. 49, 553-558.
4. Chen, S.-T., Chen, S.-Y. and Wang, K.-T. (1992) "Kinetically controlled peptide bond formation in anhydrous alcohol catalyzed by the industrial protease alcalase", J. Org. Chem. 57, 6960-6965.
5. Chen, S.-T., Kao, C.-L. and Wang, K.-T. (1995) "Alkaline protease catalysis of a secondary amine to form a peptide bond", Int. J. Peptide Protein Res. 46, 314-319.
6. Faber, K. (2000) Biotransformations in Organic Chemistry, 4th edn (Springer-Verlag, Berlin), pp 370-377.
7. Grøn H., Meldal, M. and Breddam, K. (1992) "Extensive comparison of the substrate preferences of two subtilisins as determined with peptide substrates which are based on the principle of intramolecular quenching", Biochemistry 31, 6011-6018.
8. Ito, M. and Sugiura, M. (1968) "Studies on Aspergillus proteinase. II. Purification, characterization and some properties of semi-alkaline proteinase from Aspergillus melleus", Yakugaku Zasshi 88, 1583-1590; Chem. Abstr. 70: 74538y (1969).
9. Jakubke, H.-D. (1995) "B.2.5 Hydrolysis and formation of peptides", In: Draux, K. and Waldmann, H., eds, Enzyme Catalysis in Organic Synthesis (VCH, Weinheim), pp 431-458.
10. Kitaguchi, H. (1996) "Peptide synthesis", In: Koskinen, A.M.P. and Klibanov, A.M., eds, Enzymatic Reactions in Organic Media (Blackie A & P, Glasgow), pp 224-243.
11. Kitaguchi, H. and Klibanov, A.M. (1989) "Enzymatic peptide synthesis via segment condensation in the presence of water mimics", J. Am. Chem. Soc. 111, 9272-9273.
12. Kuhl, P., Zacharias, U., Burckhardt, H. and Jakubke, H.-D. (1986) "Use of carboxamidomethyl esters in protease catalyzed peptide synthesis", Monatsh. Chem. 117, 1195-1204.
13. Lobell, M. and Schneider, M.P. (1998) "Pronase catalysed peptide syntheses", J. Chem. Soc. Perkin Trans. 1, 319-325.
14. Miyazawa, T., Iwanaga, H., Yamada, T. and Kuwata, S. (1992) "Optical resolution of unusual amino acids using microbial proteases", Chirality 4, 427-431.
15. Miyazawa, T., Minowa, H., Miyamoto, T., Imagawa, K., Yanagihara, R. and Yamada, T. (1997) "Resolution of non-protein amino acids via microbial protease-catalyzed ester hydrolysis: Marked enhancement of enantioselectivity by the use of esters with longer alkyl chains and at low temperature", Tetrahedron: Asymmetry 8, 367-370.
16. Miyazawa, T., Nakajo, S., Nishikawa, M., Hamahara, K., Imagawa, K., Ensatsu, E., Yanagihara, R. and Yamada, T. (2001a) "α-Chymotrypsin-catalysed peptide synthesis via the kinetically controlled approach using activated esters as acyl donors in organic solvents with low water content: Incorporation of non-protein amino acids into peptides", J. Chem. Soc. Perkin Trans. 1, 82-86.
17. Miyazawa, T., Tanaka, K., Ensatsu, E., Yanagihara, R. and Yamada, T. (2001b) "Broadening of the substrate tolerance of α-chymotrypsin by using the carbamoylmethyl ester as an acyl donor in the kinetically controlled peptide synthesis", J. Chem. Soc. Perkin Trans. 1, 87-93.
18. Miyazawa, T., Ensatsu, E., Yabuuchi, N., Yanagihara, R. and Yamada, T. (2002a) "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.
19. Miyazawa, T., Ensatsu, E., Hiramatsu, M., Yanagihara, R. and Yamada, T. (2002b) "α-Chymotrypsin-catalysed segment condensations via the kinetically controlled approach using carbamoylmethyl esters as acyl donors in organic media", J. Chem. Soc. Perkin Trans. 1, 396-401.
20. Miyazawa, T., Hiramatsu, M., Murashima, T. and Yamada, T. (2002c) "Aspergillus melleus protease-catalyzed peptide synthesis using the carbamoylmethyl ester as an acyl donor in 1,1,1,3,3,3-hexafluoro-2-propanol/N,N-dimethylformamide", Biotechnol. Lett. 24, 1945-1949.
21. Nakagawa, Y. (1970) "Alkaline proteinases from Aspergillus", Methods Enzymol. 19, 581-591.
22. Nishino, N., Xu, M., Mihara, H. and Fujimoto, T. (1992a) Hexafluoroisopropyl alcohol is a useful cosolvent with dimethylformamide for tryptic synthesis of peptides, Chem. Lett. 327-330.
23. Nishino, N., Xu, M., Mihara, H. and Fujimoto, T. (1992b) "Use of hexafluoroisopropyl alcohol in tryptic condensation for partially protected precursor of α-melanocyte stimulating hormone", Tetrahedron. Lett. 33, 3137-3140.
24. Schoellmann, G. and Shaw, E. (1963) "Direct evidence for the presence of histidine in the active center of chymotrypsin", Biochemistry 2, 252-255.
25. Wong, C.-H. and Whitesides, G.M. (1994) Enzymes in Synthetic Organic Chemistry (Pergamon, Oxford), pp 46-59.