Electrode mediators for regeneration of NADH and NADPH

• US 5,498,542 A
• Filed: 09/29/1994
• Issued: 03/12/1996
• Est. Priority Date: 09/29/1994
• Status: Expired due to Term

• Current Assignee: Bayer Corporation (Bayer AG)
• Original Assignee: Bayer Corporation (Bayer AG)
• Inventors: Musho, Matthew K., Corey, Paul F.
• Primary Examiner(s): Gitomer, Ralph J.
• Application Number:
  US08/314,718
• Time in Patent Office: 530 Days
• Field of Search: 435/4, 435/288, 435/177, 435/817, 429/13, 204/153.12, 204/294, 204/403, 544/35, 544/102
• US Class Current: 204/402
• CPC Class Codes: C07D 279/18 [b, e]-condensed with two six-membered rings
• CPC Class Codes: C12P 1/00 Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
• CPC Class Codes: C12Q 1/004 mediator-assisted
• CPC Class Codes: Y10S 435/817 Enzyme or microbe electrode

Abstract

Disclosed is an electrode suitable for the electrochemical regeneration of the co-enzymes NADH and NADPH. The electrode has imparted on its surface a mediator function which is a 3-methylene-3H-phenothiazine or a 3-methylene-3H-phenoxazine compound.

Claims

1. An electrode for the electrochemical regeneration of the coenzymes dihydronicotinamide adenine dinucleotide (NADH), dihydronicotinamide adenine dinucleotide phosphate (NADPH) or analogs thereof wherein there has been imparted to the electrode surface a mediator comprising one or more mediator compounds selected from the group consisting of substituted or unsubstituted 3-methylene-3H-phenothiazine and 3-methylene-3H-phenoxazine compounds represented by the formula:

##STR18## wherein Z is oxygen or sulfur, R is hydrogen, substituted or unsubstituted aryl, alkoxy, aryloxy, halo, nitro, substituted or unsubstituted amino, keto, carboxy or alkoxycarbonyl and X and Y are electron withdrawing groups.

2. The electrode of claim 1 wherein the aryl group is phenyl, naphthyl or pyridyl;

the halo group is fluoro, chloro or bromo and the alkoxy group contains 1 to 6 carbon atoms.

3. The electrode of claim 1 wherein X and Y are independently cyano, aliphatic or aromatic keto, aliphatic or aromatic ester, substituted or unsubstituted amido, trifluoromethylsulfonyl, trifluoromethylketo, nitro, lower alkylsulfonyl, trifluoromethylsulfinyl, arylsulfonyl, lower alkylketo, lower alkylsulfinyl, arylsulfinyl, polyhaloalkyl, perfluorophenyl, 2-benzoxazolyl, 2-benzthiazolyl or 5-Cl-tetrazolyl.

4. The electrode of claim 1 wherein X and Y together make up a cyclic 1,3 ketone;

a cyclic ester or a cyclic amide.

5. The electrode of claim 1 wherein the mediator is represented by the formula:

##STR19##

6. The electrode of claim 1 wherein the mediator is represented by the formula:

##STR20##

7. The electrode of claim 1 wherein the mediator is represented by the formula:

##STR21##

8. The electrode of claim 1 wherein the mediator is represented by the formula:

##STR22##

9. The electrode of claim 1 wherein the mediator is represented by the formula:

##STR23##

10. The electrode of claim 1 wherein the mediator is represented by the formula:

##STR24##

11. The electrode of claim 1 wherein the mediator is represented by the formula:

##STR25##

12. The electrode of claim 1 wherein the mediator is represented by the formula:

##STR26##

13. The electrode of claim 1 wherein the mediator is represented by the formula:

##STR27##

14. The electrode of claim 1 wherein the mediator is represented by the formula:

##STR28##

15. The electrode of claim 1 comprising graphite, pyrolytic carbon, glassy carbon, platinum or gold.