Peptide synthesis of aspartame precursor using organic-solvent-stable PST-01 protease in monophasic aqueous-organic solvent systems

Biotechnology Progress

Volumn 23, Issue 4, 2007, Pages 820-823

  Tsuchiyama, Shotaro ^a   Doukyu, Noriyuki ^b   Yasuda, Masahiro ^a   Ishimi, Kosaku ^a   Ogino, Hiroyasu ^a  

^a Osaka City University   (Japan)

^b TOYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

L-PHENYLALANINE METHYL ESTER; PST-01 PROTEASE; WATER-SOLUBLE ORGANIC SOLVENTS;

FOOD PRODUCTS; METHANOL; ORGANIC SOLVENTS; POLYETHYLENE GLYCOLS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

PEPTIDES;

ASPARTAME; BENZYLOXYCARSBONYLPHENYLALANINE CYANOMETHYL ESTER; DIMETHYL SULFOXIDE; DRUG DERIVATIVE; PEPTIDE; PEPTIDE HYDROLASE; PHENYLALANINE; PHENYLALANINE METHYL ESTER; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; BIOTECHNOLOGY; CATALYSIS; CHEMISTRY; DOSE RESPONSE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; METHODOLOGY; ORGANIC CHEMISTRY; PEPTIDE SYNTHESIS; PH;

ASPARTAME; BIOTECHNOLOGY; CATALYSIS; CHEMISTRY, ORGANIC; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIMETHYL SULFOXIDE; DOSE-RESPONSE RELATIONSHIP, DRUG; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; PEPTIDE BIOSYNTHESIS; PEPTIDE HYDROLASES; PEPTIDES; PHENYLALANINE; SOLVENTS;

EID: 34547918897     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp060382y     Document Type: Article

References (16)

1. Homandberg, G. A.; Mattis, J. A.; Laskowski, M., Jr. Synthesis of peptide bonds by proteinases. Addition of organic cosolvents shifts peptide bond equilibria toward synthesis. Biochemistry 1978, 17, 5220-5227.
2. Bordusa, F. Proteases in organic synthesis. Chem. Rev. 2002, 102, 4817-4867.
3. Kumar, D.; Bhalla, T. C. Microbial proteases in peptide synthesis: Approaches and applications. Appl. Microbiol. Biotechnol. 2005, 68, 726-736.
4. Ogino, H.; Ishikawa, H. Enzymes which are stable in the presence of organic solvents. J. Biosci. Bioeng. 2001, 91, 109-116.
5. Ogino, H.; Yasui, K.; Shiotani, T.; Ishihara, T.; Ishikawa, H. Organic solvent-tolerant bacterium which secretes an organic-solvent-stable proteolytic enzyme. Appl. Environ. Microbiol. 1995, 61, 4258-4262.
6. Ogino, H.; Watanabe, F.; Yamada, M.; Nakagawa, S.; Hirose, T.; Noguchi, A.; Yasuda, M.; Ishikawa, H. Purification and characterization of organic solvent-stable protease from organic solvent-tolerant Pseudomonas aeruginosa PST-01. J. Biosci. Bioeng. 1999, 87, 61-68.
7. Ogino, H.; Yamada, M.; Watanabe, F.; Ichinose, H.; Hirose, T.; Yasuda, M.; Ishikawa, H. Peptide synthesis catalyzed by organic solvent-stable protease from Pseudomonas aeruginosa PST-01 in monophasic aqueous-organic solvent systems. J. Biosci. Bioeng. 1999, 88, 513-518.
8. Ogino, H.; Gemba, Y.; Yamada, M.; Shizuka, M.; Yasuda, M.; Ishikawa, H. The synthetic rate of dipeptide catalyzed by organic solvent-stable protease from Pseudomonas aeruginosa PST-01 in the presence of water-soluble organic solvents. Biochem. Eng. J. 2000, 5, 219-223.
9. Bobe, L. M.; Abdelmoez, W.; Ogino, H.; Yasuda, M.; Ishimi, K.; Ishikawa, H. Kinetics and mechanism of a reaction catalyzed by PST-01 protease from Pseudomonas aeruginosa PST-01. Biotechnol. Bioeng. 2004, 86, 365-373.
10. Kuhn, D.; Durrschmidt, P.; Mansfeld, J.; Ulbrich-Hofmann, R. Boilysin and thermolysin in dipeptide synthesis: a comparative study. Biotechnol. Appl. Biochem. 2002, 36, 71-76.
11. Nakanishi, K.; Kimura, Y.; Matsuno, R. Kinetics and equilibrium of enzymatic synthesis of peptides in aqueous/organic biphasic systems. Eur. J. Biochem. 1986, 161, 541-549.
12. Ogino, H.; Yokoo, J.; Watanabe, F.; Ishikawa, H. Cloning and sequencing of a gene of organic solvent-stable protease secreted from Pseudomonas aeruginosa PST-01 and its expression in Escherichia coli. Biochem. Eng. J. 2000, 5, 191-200.
13. Ogino, H.; Uchiho, T.; Yokoo, J.; Kobayashi, R.; Ichise, R.; Ishikawa, H. Role of intermolecular disulfide bonds of the organic solvent-stable PST-01 protease in the organic solvent-stability. Appl. Environ. Microbiol. 2001, 67, 942-947.
14. Nakanishi, K.; Kamikubo, T.; Matsuno, R. Continuous synthesis of N-(benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester with immobilized thermolysin in an organic solvent. Bio/Technology 1985, 3, 459-464.
15. Fastrez, J.; Fersht, A. R. Demonstration of the acyl-enzyme mechanism for the hydrolysis of peptides and anilides by chymotrypsin. Biochemistry 1973, 12, 2025-2034.
16. Hangauer, D. G.; Monzingo, A. F.; Matthews, B. W. An interactive computer graphics study of thermolysin-catalyzed peptide cleavage and inhibition by N-carboxymethyl dipeptides. Biochemistry 1984, 23, 5730-5741.