Process development for the electroenzymatic synthesis of (R)-methylphenylsulfoxide by use of a 3-dimensional electrode

Biotechnology and Bioengineering

Volumn 98, Issue 3, 2007, Pages 525-534

  Lutz S ^a   Vuorilehto, K ^b   Liese, A ^c  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

^b AALTO UNIVERSITY   (Finland)

^c HAMBURG UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Caldariomyces fumago; Chiral sulfoxide; Chloroperoxidase; Electrochemical cell; Electroenzymatic synthesis

Indexed keywords

CALDARIOMYCES FUMAGO; CHIRAL SULFOXIDE; CHLOROPEROXIDASE; ELECTROENZYMATIC SYNTHESIS; ELECTROGENERATION;

DISSOLVED OXYGEN; ELECTROCHEMICAL CELLS; ELECTRODES; ENZYME ACTIVITY; GRAPHITE; REDUCTION; SYNTHESIS (CHEMICAL);

HYDROGEN PEROXIDE;

CHLORIDE PEROXIDASE; GRAPHITE; HYDROGEN PEROXIDE; METHYLPHENYLSULFOXIDE; ORGANOSULFUR DERIVATIVE; TERT BUTYL ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CHEMICAL PROCEDURES; ELECTROCHEMISTRY; ELECTROENZYMATIC SYNTHESIS; OXIDATION; PARAMETER; PROCESS DEVELOPMENT; THREE DIMENSIONAL IMAGING;

CATALYSIS; CHLORIDE PEROXIDASE; ELECTROCHEMISTRY; EQUIPMENT DESIGN; EQUIPMENT FAILURE ANALYSIS; HYDROGEN PEROXIDE; MICROELECTRODES; OXYGEN; SULFOXIDES;

LEPTOXYPHIUM FUMAGO;

EID: 35048839314     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.21434     Document Type: Article

References (34)

1. Bartlett PN, Pletcher D, Zeng J. 1999. Approaches to the integration of electrochemistry and biotechnology - II. The horseradish peroxidase catalyzed oxidation of 2,4,6-trimethylphenol by electrogenerated hydrogen peroxide. J Electrochem Soc 146(3):1088-1092.
2. Chen JK, Nobe K. 1993. Oxidation of dimethylaniline by horseradish-peroxidase and electrogenerated peroxide. 1. Free enzyme studies. J Electrochem Soc 140(2):299-303.
3. Dembitsky VM. 2003. Oxidation, epoxidation and sulfoxidation reactions catalysed by haloperoxidases. Tetrahedron 59(26):4701-4720.
4. DIN EN 25 813. 1992. Normenausschuss Wasserwesen e.V. Bestimmung des gelösten Sauerstoffs - Iodometrisches Verfahren (ISO 5813: 1983) EN 25 813.
5. Hager LP, Morris DR, Brown FS, Eberwein H. 1966. Chloroperoxidase. 2. Ultilization of Halogen Anions. J Biol Chem 241(8):1769-1777.
6. Hernandez CEL, Lütz S, Liese A, Bon EPS. 2005. Activity and stability of Caldariomyces fumago chloroperoxidase modified by reductive alkylation, amidation and cross-linking. Enzyme Microb Technol 37(6):582-588.
7. Hollmann F, Schmid A. 2004. Electrochemical regeneration of oxidoreductases for cell-free biocatalytic redox reactions. Biocatal Biotransfor 22(2):63-88.
8. Kohlmann C, Lũtz S. 2006. Electroenzymatic synthesis of chiral sulfoxides. Eng Life Sci 6(2):170-174.
9. La Rotta CE, Bon EPS. 2002. 4-chlorophenol degradation by chloroperoxidase from Caldariomyces fumago - Formation of insoluble products. Appl Biochem Biotechnol 98:191-203.
10. Laane C, Weyland A, Franssen M. 1986. Bioelectrosynthesis of halogenated compounds using chloroperoxidase. Enzyme Microb Technol 8(6):345-348.
11. Lee K, Moon SH. 2003. Electroenzymatic oxidation of veratryl alcohol by lignin peroxidase. J Biotechnol 102(3):261-268.
12. Liese A. 2005. Technical application of biological principles in asymmetric catalysis. Adv Biochem Eng/Biotechn 92:197-224.
13. Liese A, Seelbach K, Wandrey C. 2006. Industrial Biotransformation. Weinheim: Wiley-VCH.
14. Lütz S, Steckhan E, Liese A. 2004. First asymmetric electroenzymatic oxidation catalyzed by a peroxidase. Electrochem Commun 6(6):583-587.
15. Morris DR, Hager LP. 1965. Chloroperoxidase. I. Isolation and properties of the crystalline glycoprotein. J Biol Chem 241(8):1763-1768.
16. Park JB, Clark DS. 2006. Deactivation mechanisms of chloroperoxidase during biotransformations. Biotechnol Bioeng 93(6):1190-1195.
17. Pletcher D. 1999. Indirect oxidations using electrogenerated hydrogen peroxide. Acta Chem Scand 53(10):745-750.
18. Schröder I, Steckhan E, Liese A. 2003. In situ NAD(+) regeneration using 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) as an electron transfer mediator. J Electroanal Chem 541:109-115.
19. Seelbach K, vanDeurzen MPJ, vanRantwijk F, Sheldon RA, Kragl U. 1997. Improvement of the total turnover number and space-time yield for chloroperoxidase catalyzed oxidation. Biotechnol Bioeng 55(2):283-288.
20. Steckhan E. 1994. Electroenzymatic synthesis. Top Curr Chem 170:83-111.
21. Steckhan E, Arns T, Heineman WR, Hilt G, Hoormann D, Jorissen J, Kroner L, Lewall B, Pütter H. 2001. Environmental protection and economization of resources by electroorganic and electroenzymatic syntheses. Chemosphere 43(1):63-73.
22. Tamminen A, Vuorilehto K. 1997. Application of a three-dimensional ion-exchange electrolyte in the deoxygenation of low-conductivity water. J Appl Electrochem 27(9):1095-1099.
23. Tamminen A, Vuorilehto K, Ylasaari S. 1996. Scale-up of an electrochemical cell for oxygen removal from water. J Appl Electrochem 26(1):113-117.
24. van de Velde F, van Rantwijk F, Sheldon RA. 1999. Selective oxidations with molecular oxygen, catalyzed by chloroperoxidase in the presence of a reductant. J Mol Catal B Enzym 6(5):453-461.
25. van de Velde F, Lourenco ND, Bakker M, van Rantwijk F, Sheldon RA. 2000. Improved operational stability of peroxidases by coimmobilization with glucose oxidase. Biotechnol Bioeng 69(3):286-291.
26. van de Velde F, Bakker M, van Rantwijk F, Rai GP, Hager LP, Sheldon RA. 2001. Engineering chloroperoxidase for activity and stability. J Mol Catal B Enzym 11(4-6):765-769.
27. van Deurzen MPJ, Remkes IJ, vanRantwijk F, Sheldon RA. 1997a. Chloroperoxidase catalyzed oxidations in t-butyl alcohol/water mixtures. J Mol Catal A Chem 117(1-3):329-337.
28. van Deurzen MPJ, Seelbach K, VanRantwijk F, Kragl U, Sheldon RA. 1997b. Chloroperoxidase: Use of a hydrogen peroxide-stat for controlling reactions and improving enzyme performance. Biocatal Biotransfor 15(1):1-16.
29. van Deurzen MPJ, van Rantwijk F, Sheldon RA. 1997c. Selective oxidations catalyzed by peroxidases. Tetrahedron 53(39):13183-13220.
30. Vuorilehto K. 1997. Application of three-dimensional electrodes and the problem of potential distribution. Helsinki: Helsinki University of Technology.
31. Vuorilehto K, Tamminen A. 1997. Application of a solid ion-exchange electrolyte three-dimensional electrodes. J Appl Electrochem 27(7): 749-755.
32. Vuorilehto K, Tamminen A, Ylasaari S. 1995. Electrochemical removal of dissolved-oxygen from water. J Appl Electrochem 25(10):973-977.
33. Vuorilehto K, Lütz S, Wandrey C. 2004. Indirect electrochemical reduction of nicotinamide coenzymes. Bioelectrochemistry 65:1-7.
34. Wandrey C. 2004. Biochemical reaction engineering for redox reactions. Chem Record 4(4):254-265.