Highly efficient synthesis of endomorphin-2 under thermodynamic control catalyzed by organic solvent stable proteases with in situ product removal

Bioresource Technology

Volumn 129, Issue , 2013, Pages 663-666

  Xu, Jiaxing ^a   Sun, Honglin ^a   He, Xuejun ^a   Bai, Zhongzhong ^a   He, Bingfang ^a  

^a NANJING TECH UNIVERSITY   (China)

Author keywords

Endomorphin 2; Enzymatic synthesis; In situ product removal; Organic solvent stable protease; Thermodynamic control

Indexed keywords

ENZYME ACTIVITY; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL); THERMODYNAMICS;

BIPHASIC SYSTEMS; DRIVING FORCES; EFFICIENT SYNTHESIS; ENDOMORPHIN-2; ENZYMATIC PROCESS; ENZYMATIC SYNTHESIS; HIGH PRODUCTIVITY; HIGH STABILITY; HIGH YIELD; MOLAR RATIO; NON-AQUEOUS; NONAQEOUS; ORGANIC SOLVENT-TOLERANT PROTEASE; REACTION MEDIA; SCALE-UP; SITU PRODUCT REMOVAL; SOLVENT STABLES; SYNTHETIC REACTIONS; TETRAPEPTIDE; THERMODYNAMIC CONTROL; THERMODYNAMIC EQUILIBRIA;

ORGANIC SOLVENTS;

ENDOMORPHIN 2; ORGANIC SOLVENT; PROTEINASE; TETRAPEPTIDE;

AQUEOUS SOLUTION; CATALYST; ENZYME ACTIVITY; PEPTIDE; PURIFICATION; REACTION KINETICS; REMOVAL EXPERIMENT; SOLVENT; THERMODYNAMICS;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENZYME SYNTHESIS; PRIORITY JOURNAL; THERMODYNAMICS;

EID: 84873648382     PISSN: 09608524     EISSN: 18732976     Source Type: Journal    
DOI: 10.1016/j.biortech.2012.12.036     Document Type: Article

References (20)

1. Biondi B., Giannini E., Negri L., Melchiorri P., Lattanzi R., Rosso F., Ciocca L., Rocchi R. Opioid peptides: synthesis and biological activity of new endomorphin analogues. Int. J. Pept. Res. Ther. 2006, 12:145-151.
2. Bordusa F. Proteases in organic synthesis. Chem. Rev. 2002, 102:4817-4868.
3. Bornscheuer U.T., Huisman G.W., Kazlauskas R.J., Lutz S., Moore J.C., Robins K. Engineering the third wave of biocatalysis. Nature 2012, 485:185-194.
4. Carrea G., Riva S. Properties and synthetic applications of enzymes in organic solvents. Angew. Chem. Int. Ed. 2000, 39:2226-2254.
5. Chiravuri M., Agarraberes F., Mathieu S.L., Lee H., Huber B.T. Vesicular localization and characterization of a novel post-proline-cleaving aminodipeptidase, quiescent cell proline dipeptidase. J. Immunol. 2000, 165:5695-5702.
6. Fernández-Lucas J., Fresco-Taboada Alba., de la Mata I., Arroyo Miguel. One-step enzymatic synthesis of nucleosides from low water-soluble purine bases in non-conventional media. Bioresour. Technol. 2012, 115:63-69.
7. Granic I., Masman M.F., Mulder K.C., Nijholt I.M., Naude P.J.W., de Haan A., Borbély E., Penke B., Luiten P.G., Eisel U.L. LPYFDa neutralizes amyloid-beta-induced memory impairment and toxicity. J. Alzheimers Dis. 2010, 19:991-1005.
8. Gupta A., Khare S.K. A protease stable in organic solvents from solvent tolerant strain of Pseudomonas aeruginosa. Bioresour. Technol. 2006, 97:1788-1793.
9. Ivanov I.P., Kasche V., Petkov D.D. Thermodynamics of enzymic peptide synthesis in biphasic aqueous-organic systems: coupling of the chemical and phase equilibria. Biocatal. Biotransform. 1996, 14:181-194.
10. Jakubke H., Kuhl P., Könnecke A. Basic principles of protease-catalyzed peptide bond formation. Angew. Chem. Int. Ed. Engl. 1985, 24:85-93.
11. Liu W.X., Wang R. Endomorphins: potential roles and therapeutic indications in the development of opioid peptide analgesic drugs. Med. Res. Rev. 2012, 32:536-580.
12. Rahman R.N.Z.A., Geok L.P., Basri M., Salleh A.B. Physical factors affecting the production of organic solvent-tolerant protease by Pseudomonas aeruginosa strain K. Bioresour. Technol. 2005, 96:429-436.
13. Salam S.M.A., Kagawa K., Kawashiro K. α-Chymotrypsin-catalyzed peptide synthesis using N-protected D-amino acid carbamoylmethyl esters as acyl donors. Tetrahedron Asymmetry 2006, 17:22-29.
14. Semenov A.N., čeřovský V., Titov M.I., Martinek K. Enzymes in preparative organic synthesis: the problem of increasing the yield of product. Collect. Czech. Chem. Commun. 1988, 53:2963-2985.
15. Shi Z.H., Wei Y.Y., Wang C.J., Yu L. Synthesis and analgesic activities of endomorphin-2 and its analogues. Chem. Biodivers. 2007, 4:458-467.
16. Sun H.L., He B.F., Xu J.X., Wu B., Ouyang P.K. Efficient chemo-enzymatic synthesis of endomorphin-1 using organic solvent stable proteases to green the synthesis of the peptide. Green Chem. 2011, 13:1680-1685.
17. Tang X.Y., Pan Y., Li S., He B.F. Screening and isolation of an organic solvent-tolerant bacterium for high-yield production of organic solvent-stable protease. Bioresour. Technol. 2008, 99:7388-7392.
18. Tang X.Y., Wu B., Ying H.J., He B.F. Biochemical properties and potential applications of a solvent-stable protease from the high-yield protease producer Pseudomonas aeruginosa PT121. Appl. Biochem. Biotechnol. 2010, 160:1017-1031.
19. Tufvesson P., Lima-Ramos J., Jensen J., Al-Haque N., Neto W., Woodley J. Process considerations for the asymmetric synthesis of chiral amines using transaminases. Biotechnol. Bioeng. 2011, 108:1479-1493.
20. Xu J.X., Jiang M., Sun H.L., He B.F. An organic solvent-stable protease from organic solvent-tolerant Bacillus cereus WQ9-2: purification, biochemical properties, and potential application in peptide synthesis. Bioresour. Technol. 2010, 101:7991-7994.