IP Library › Granted Patent US 10,577,637
Granted Patent B2
US 10,577,637 · App. 15/294,374 · Granted Mar 3, 2020

Enzyme electrode

Inventors: Koji Katsuki (Kyoto, JP); Hisashi Kaneda (Kyoto, JP); Junko Shimazaki (Tokyo, JP)
Assignees: ARKRAY, Inc.; Ultizyme International Ltd.
C12Q1/006C12Q1/001C12Q1/25C12Q1/32C23C14/0605C23C14/205C23C14/24C23C14/34C23C14/58C23C16/06C23C16/44C23C16/56C23C28/00G01N27/3271G01N27/3272
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,577,637
App. No.
15/294,374
Granted
Mar 3, 2020
Kind
B2
Abstract

An enzyme electrode includes an electrode, and a detection layer which contacts the electrode and contains a crosslinking agent, an electrically conductive macromolecule and an enzyme transferring and receiving electrons to and from the electrode and does not contain an electron transfer subunit.

Claims (32)

1. A direct electron transfer-type enzyme electrode comprising:

an electrode; and

a detection layer which contacts the electrode and contains an oxazoline group-containing compound, trehalose, an electrically conductive macromolecule and an enzyme transferring and receiving electrons to and from the electrode, wherein said detection layer does not contain an electron mediator,

wherein said enzyme is cytochrome glucose dehydrogenase which does not contain an electron transfer subunit, and

wherein said electrically conductive macromolecule is selected from the group consisting of polypyrrole, polystyrene sulfonate, polythiophene, polyisothianaphthene, polyethylene dioxythiophene(poly(3,4-ethylenedioxythiophene)poly(styrenesulfonate)), and the combinations thereof.

2. The direct electron transfer-type enzyme electrode according to claim 1 , wherein said detection layer further contains electrically conductive particles.

3. The direct electron transfer-type enzyme electrode according to claim 1 , wherein said electrically conductive macromolecule is polypyrrole.

4. The direct electron transfer-type enzyme electrode according to claim 1 , wherein said electrically conductive macromolecule comprises polystyrene sulfonate.

5. The direct electron transfer-type enzyme electrode according to claim 1 , wherein said electrically conductive macromolecule comprises polythiophene.

6. The direct electron transfer-type enzyme electrode according to claim 1 , wherein said electrically conductive macromolecule comprises polyisothianaphthene.

7. The direct electron transfer-type enzyme electrode according to claim 1 , wherein said electrically conductive macromolecule comprises polyethylene dioxythiophene(poly(3,4-ethylenedioxythiophene)poly(styrene sulfonate)).

8. The direct electron transfer-type enzyme electrode according to claim 1 , wherein the oxazoline group-containing compound comprises one selected from the group consisting of 2,2′-bis-(2-oxazoline),2,2′-methylene-bis-(2-oxazoline), 2,2′-ethylene-bis-(2-oxazoline),2,2′-trimethylene-bis-(2-oxazoline),2,2′-tetramethylene-bis-(2-oxazoline),2,2′-hexamethylene-bis-(2-oxazoline),2,2′-octamethylene-bis-(2-oxazoline),2,2′-ethylene-bis-(4,4′-dimethyl-2-oxazoline),2,2′-p-phenylene-bis-(2-oxazoline), 2,2′-m-phenylene-bis-(2-oxazoline),2,2′-m-phenylene-bis-(4,4′-dimethyl-2-oxazoline),bis-(2-oxazolinylcyclohexane) sulfide, and bis-(2-oxazolinylnorbornane)sulfide.

9. The direct electron transfer-type enzyme electrode according to claim 1 , wherein the oxazoline group-containing compound comprises polymerizable oxazoline compound selected from the group consisting of 2-vinyl-2-oxazoline, 2-vinyl-4-methyl-2-oxazoline, 2-vinyl-5-methyl-2-oxazoline, 2-isopropenyl-2-oxazoline, 2-isopropenyl-4-methyl-2-oxazoline, 2-isopropenyl-5-ethyl-2-oxazoline, and polymerized or copolymerized compounds of one or more thereof.

10. A method of manufacturing a direct electron transfer-type enzyme electrode, comprising:

forming, on an electrode, a detection layer which contacts the electrode and contains an oxazoline group-containing compound-, trehalose, an electrically conductive macromolecule and an enzyme transferring, wherein said detection layer does not contain an electron mediator, and

receiving electrons to and from the electrode,

wherein said enzyme is cytochrome glucose dehydrogenase and does not contain an electron transfer subunit, and

wherein said electrically conductive macromolecule is selected from the group consisting of polypyrrole, polystyrene sulfonate, polythiophene, polyisothianaphthene, polyethylene dioxythiophene(poly(3,4-ethylenedioxythiophene)poly(styrenesulfonate)), and the combinations thereof.

11. The method according to claim 10 , wherein said detection layer further contains electrically conductive particles.

12. The direct electron transfer-type enzyme electrode according to claim 10 , wherein said electrically conductive macromolecule comprises polystyrene sulfonate.

13. The direct electron transfer-type enzyme electrode according to claim 10 , wherein said electrically conductive macromolecule comprises polythiophene.

14. The direct electron transfer-type enzyme electrode according to claim 10 , wherein said electrically conductive macromolecule comprises polyisothianaphthene.

15. The direct electron transfer-type enzyme electrode according to claim 10 , wherein said electrically conductive macromolecule comprises polyethylene dioxythiophene(poly(3,4-ethylenedioxythiophene)poly(styrenesulfonate)).

16. The direct electron transfer-type enzyme electrode according to claim 10 , wherein the oxazoline group-containing compound comprises one selected from the group consisting of 2,2′-bis-(2-oxazoline), 2,2′-methylene-bis-(2-oxazoline), 2,2′-ethylene-bis-(2-oxazoline),2,2′-trimethylene-bis-(2-oxazoline),2,2′-tetramethylene-bis-(2-oxazoline),2,2′-hexamethylene-bis-(2-oxazoline),2,2′-octamethylene-bis-(2-oxazoline),2,2′-ethylene-bis-(4,4′-dimethyl-2-oxazoline),2,2′-p-phenylene-bis-(2-oxazoline), 2,2′-m-phenylene-bis-(2-oxazoline),2,2′-m-phenylene-bis-(4,4′-dimethyl-2-oxazoline),bis-(2-oxazolinylcyclohexane) sulfide, and bis-(2-oxazolinylnorbornane)sulfide.

17. The direct electron transfer-type enzyme electrode according to claim 10 , wherein the oxazoline group-containing compound comprises polymerizable oxazoline compound selected from the group consisting of 2-vinyl-2-oxazoline, 2-vinyl-4-methyl-2-oxazoline, 2-vinyl-5-methyl-2-oxazoline, 2-isopropenyl-2-oxazoline, 2-isopropenyl-4-methyl-2-oxazoline, 2-isopropenyl-5-ethyl-2-oxazoline, and polymerized or copolymerized compounds of one or more thereof.

18. A direct electron transfer-type enzyme electrode comprising:

an electrode; and

a detection layer which contacts the electrode and contains a crosslinking agent, trehalose, an electrically conductive macromolecule and an enzyme transferring and receiving electrons to and from the electrode, wherein said detection layer does not contain an electron mediator,

wherein said enzyme is cytochrome glucose dehydrogenase which does not contain an electron transfer subunit,

wherein said crosslinking agent is selected from the group consisting of aldehyde group-containing compounds, maleimide group-containing compounds, oxazoline group-containing compounds, and epoxy group-containing compounds, and

wherein said electrically conductive macromolecule is selected from the group consisting of polypyrrole, polyaniline, polystyrene sulfonate, polythiophene, polyisothianaphthene, polyethylene dioxythiophene(poly(3,4-ethylenedioxythiophene)poly(styrenesulfonate)), and the combinations thereof.

19. The direct electron transfer-type enzyme electrode according to claim 18 , wherein said detection layer further contains electrically conductive particles.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 13, 2023
From: ULTIZYME INTERNATIONAL LTD.
To: ARKRAY, INC.
Reel/Frame 062675/0251 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 15, 2017
From: KATSUKI, KOJI; KANEDA, HISASHI; SHIMAZAKI, JUNKO
To: ARKRAY, INC.; ULTIZYME INTERNATIONAL LTD.
Reel/Frame 041261/0710 →
Priority Claims (2)
JP 2015-204033 · Oct 15, 2015 · national
JP 2016-196930 · Oct 5, 2016 · national
Continuity (1)
Related Publication 20170107555A1 · Apr 20, 2017