Enzymatic synthesis of activated esters and their subsequent use in enzyme-based peptide synthesis

Journal of Molecular Catalysis B: Enzymatic

Volumn 71, Issue 1-2, 2011, Pages 79-84

  Nuijens, Timo ^a,b   Cusan, Claudia ^a   Schepers, Annette C H M ^a   Kruijtzer, John A W ^b   Rijkers, Dirk T S ^b   Liskamp, Rob M J ^b   Quaedflieg, Peter J L M ^a  

^a DSM RESOLVE   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Alcalase CLEA; Cal B; Esterification; Kinetic coupling; Peptide synthesis

Indexed keywords

2 ,2 ,2-TRIFLUOROETHANOL; ACTIVATED ESTER; ACYL DONORS; ALCALASE-CLEA; CAL-B; COST-EFFICIENT; ENZYMATIC SYNTHESIS; ESTER MOIETIES; ESTER SYNTHESIS; KINETIC COUPLING; PEPTIDE SYNTHESIS; PROLINE RESIDUES; STERICALLY DEMANDING;

AMINO ACIDS; CAMS; ENZYME ACTIVITY; ESTERIFICATION; ESTERS; ETHANOL; PEPTIDES;

BIOSYNTHESIS;

CARBOXAMIDOMETHYL ESTER; ENZYME; ESTER; GUANIDINOPHENYL ESTER; NUCLEOPHILE; PEPTIDE; SUBTILISIN; TRIACYLGLYCEROL LIPASE; TRIFLUOROETHANOL; TRIFLUOROETHY ESTER; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA; CANDIDA ANTARTICA; ENZYME SYNTHESIS; NONHUMAN; ONE POT SYNTHESIS; PEPTIDE SYNTHESIS;

EID: 79956096557     PISSN: 13811177     EISSN: 18733158     Source Type: Journal    
DOI: 10.1016/j.molcatb.2011.03.012     Document Type: Article

References (31)

1. (a) B. Steffansen, C.U. Nielsen, S. Frokjaer, Eur. J. Pharm. Biopharm. 60 (2005) 241-245;
2. (b) K. Adermann, Curr. Prot. Pept. Sci. 6 (2005) 205-206.
3. (a) H. Korhonen, A. Pihlanto, Curr. Pharm. Des. 9 (2003) 1297-1308;
4. (b) J. Torres-Llanez, B. Vallejo-Cordoba, A.F. González- Córdova, Arch. Latinoam. Nutr. 55 (2005) 111-117;
5. (c) H. Korhonen, A. Pihlanto, Curr. Pharm. Des. 13 (2007) 829-843;
6. (d) M.B. Roberfroid, J. Nutr. 137 (2007) 2493-2502.
7. D. Hans, P.R. Young, D.D.P. Fairlie, Med. Chem. 2 (2006) 627-646.
8. F. Guzmán, S. Barberis, A. Illanes, J. Biotechnol. 10 (2007) 279-314.
9. F. Bordusa, Chem. Rev. 102 (2002) 4817-4867.
10. V. Čeřovsky, F. Bordusa, J. Pept. Res. 55 (2000) 325-329.
11. T. Miyazawa, E. Ensatsu, N. Yabuuchi, R. Yanagihara, T. Yamada, J. Chem. Soc. Perkin Trans. 1 (2002) 390-395.
12. T. Miyazawa, S. Nakajo, M. Nishikawa, K. Hamahara, K. Imagawa, E. Ensatsu, R. Yanagihara, T. Yamada, J. Chem. Soc. Perkin Trans. 1 (2001) 82-86.
13. (a) S.M.A. Salam, K.-I. Kagawa, K. Kawashiro, Biotechnol. Lett. 27 (2005) 1199-1203;
14. (b) F. Bordusa, Braz. J. Med. Biol. Res. 33 (2000) 469-485.
15. M. Capellas, M.D. Benaiges, G. Caminal, G. Gonzalez, J. Lopez-Santín, P. Clapés, Biotechnol. Bioeng. 50 (2000) 700-708.
16. M.K. Dhaon, R.K. Olsen, K. Ramasamy, J. Org. Chem. 47 (1982) 1962-1965.
17. R.A. Sheldon, Biochem. Soc. Trans. 35 (2007) 1583.
18. W. König, R. Geiger, Chem. Ber. 103 (1970) 788-798.
19. W. H. J. Boesten, P.J. L. M. Quaedflieg, WO Patent No. 6222013, 1999.
20. T. Miyazawa, E. Ensatsu, M. Hiramatsu, R. Yanagihara, T. Yamada, J. Chem. Soc. Perkin Trans. 1 (2002) 396-401.
21. O.J. Park, H.G. Park, J.W. Yang, Biotechnol. Lett. (1996) 473-478.
22. T. Nuijens, C. Cusan, T.J.G.M. van Dooren, H.M.Moody, R. Merkx, J.A.W. Kruijtzer, D.T.S. Rijkers, R.M.J. Liskamp, P.J.L.M. Quaedflieg, Adv. Synth. Catal. 352 (2010) 2399-2404.
23. S.T. Chen, S.Y. Chen, C.L. Kao, K.T. Wang, Bioorg. Med. Chem. Lett. 4 (1994) 443-448.
24. J.U. Klein, A. Prykhodzka, V. Čeřovsky, J. Pept. Sci 6 (2000) 541-549.
25. (a) T. Nuijens, C. Cusan, J.A.W. Kruijtzer, D.T.S. Rijkers, R.M.J. Liskamp, P.J.L.M. Quaedflieg, Synthesis 5 (2009) 809-814;
26. (b) T. Nuijens, J.A.W. Kruijtzer, C. Cusan, D.T.S. Rijkers, R.M.J. Liskamp, P.J.L.M. Quaedflieg, Tetrahedron Lett. 50 (2009) 2719-2721.
27. F. Gini, I.F. Eggen, D.J. van Zoelen, C. Boeriu, Chimica Oggi 27 (2009) 24-26.
28. (a) D.I. Mundy, W.J. Strittmatter, Cell 40 (1985) 645-656;
29. (b) A. Koide, M. Yoshizawa, K. Kurachi, Eur. J. Biochem. 117 (1981) 383-388;
30. (c) K. Olesen, M.C. Kielland-Brandt, Protein Eng. 6 (1993) 409-415;
31. (d) Y. Bai, R. Hayashi, J. Biol. Chem. 254 (1979) 8473-8479.