Back to results
US 12,723,272 B2Granted
Mediator
AssigneeKikkoman Corporation
InventorsYosuke Masakari, Naoya Totsuka, Yasutomo Shinohara
Life of this patent
Estimating the term…
Abstract
Provided is a novel mediator. The present invention relates to a novel mediator, and an electrode modifying agent and an electron transfer promoting agent comprising the mediator, an electrode, a battery, a composition, and an enzyme sensor comprising the electrode modifying agent or the electron transfer promoting agent, and a method using any of these.
Claims15
A composition comprising:
- an enzyme;
- and
- an electrode modifying agent or an electron transfer promoting agent comprising a compound having a property of being adsorbed, without being bound to a polymer or without being polymerized, onto an electrode untreated with an acid,
- wherein the compound is a compound having a structure of formula I or formula II:
- wherein
- R1 is —NR7R8, —N═N—R9, or —N+≡N,
- R2 is —NR10R11 or —N═N—R12,
- R7 and R8 are each independently hydrogen, or linear or branched C1-7 alkyl, C1-7 alkenyl, C1-7 alkynyl, C3-9 cycloalkyl, phenyl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, acetyl, carboxy, furanylformyl, pyrazolylformyl, 1-methyl-1H-pyrazol-5-ylformyl, 9,9-dimethylfluoren-2-yl, —N+≡N, —N═N-phenyl, benzyl,
- which may optionally be substituted with one or more X or V,
- R10 is hydrogen, or linear or branched C1-7 alkyl, C1-7 alkenyl, C1-7 alkynyl, C3-9 cycloalkyl, phenyl, 1-naphthyl, 2-naphthyl, anthracenyl or phenanthrenyl, which may optionally be substituted with one or more X or V,
- R3, R4, R5 and Re are each independently hydrogen, or linear or branched C1-7 alkyl, C1-7 alkenyl, C1-7 alkynyl, C1-7 alkoxy, halo, nitro, cyano, carboxy, sulfo, hydroxy or amino, which may optionally be substituted with one or more Y,
- or R3 and R4, or R5 and Re, together with the benzene ring containing these moieties, form a benzene ring, or
- which may optionally be substituted with one or more oxo, X or W,
- wherein * is bonded to the carbon atom bonded to R3, and ** is bonded to the carbon atom bonded to R4, or * is bonded to the carbon atom bonded to R5, and ** is bonded to the carbon atom bonded to R6,
- R11 is selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, anthracenyl and phenanthrenyl, which may optionally be substituted with one or more X or Z,
- R9 is selected from the group consisting of hydrogen, and phenyl, 1-naphthyl, 2-naphthyl, anthracenyl and phenanthrenyl, which may optionally be substituted with one or more X,
- R12 is selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, and
- which may optionally be substituted with one or more X, W, isothiocyanate, or halosulfonyl,
- wherein
- V is —O-acryloyl, acetylamino, or phenyl, which may optionally be substituted with C1-7 alkyl, W is D- or L-alanylsulfonyl, D- or L-valylsulfonyl, D- or L-leucylsulfonyl, D- or L-methionylsulfonyl, D- or L-prolylsulfonyl, D- or L-tryptophylsulfonyl, D- or L-glycylsulfonyl, D- or L-cysteinylsulfonyl, D- or L-isoleucylsulfonyl, D- or L-phenylalanylsulfonyl, D- or L-tyrosylsulfonyl, D- or L-serylsulfonyl, D- or L-threonylsulfonyl, D- or L-asparaginylsulfonyl, D- or L-glutamylsulfonyl, D- or L-arginylsulfonyl, D- or L-histidylsulfonyl, D- or L-lysylsulfonyl, D- or L-asparagylsulfonyl, D- or L-glutaminylsulfonyl, -C(═O)—O-succinimidyl, acetyl, trifluoroacetyl, benzoylamino, —N═N-phenyl, phenylamino, or diaminophenylazophenyl, which may optionally be substituted with one or more amino, C1-7 alkyl, or aminoalkyl, or phenylazo, which may optionally be substituted with one or more X, naphthylazo, which may optionally be substituted with one or more Y, acetylamino,
- X is linear or branched C1-7 alkyl, C1-7 alkenyl, C1-7 alkynyl, C1-7 alkoxy, halo, hydroxy, nitro, carboxy, cyano, sulfo, amino or alkylamino, which may optionally be substituted with one or more substituents selected from the group consisting of halo, amino, cyano, carboxy, carbonyl, alkoxy, alkylamino, nitroso, nitro and sulfo,
- Y is selected from the group consisting of halo, amino, cyano, carboxy, carbonyl, hydroxy, alkoxy and sulfo, and
- Z is —SO2—CH═CH2, —SO2—C2H4—O—SO3H, or 4,6-dichlorotriazin-2-ylamino,
- or a salt, an anhydride or a solvate thereof,
- wherein the compound is neither N-methyl-N-phenyl-1,4-phenylenediamine nor N-methyl-N-(3-methoxyphenyl)-1,4-phenylenediamine, and
- wherein the compound is neither
23 more elements
A composition comprising:
- an enzyme;
- and
- an electrode modifying agent or an electron transfer promoting agent comprising a compound having a property of being adsorbed, without being bound to a polymer or without being polymerized, onto an electrode untreated with an acid,
- wherein the compound is a compound having a structure of formula Ia or Ila:
- wherein
- R1a is —NR7aR8a, —N═N—R9a, or —N+≡N,
- R2a is —NR10aR11a, or —N═N—R12a,
- R7a and R8a are each independently hydrogen, or linear or branched C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, C3-9 cycloalkyl, phenyl, 1-naphthyl, 2-naphthyl, anthracenyl, or phenanthrenyl, which may optionally be substituted with one or more Xa,
- R10 is hydrogen, or linear or branched C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, C3-9 cycloalkyl, phenyl, 1-naphthyl, 2-naphthyl, anthracenyl or phenanthrenyl, which may optionally be substituted with one or more Xa,
- R3a, R4a, R5a and R6a are each independently hydrogen, or linear or branched C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, C1-6 alkoxy, halo, nitro, cyano, carboxy, sulfo, hydroxy or amino, which may optionally be substituted with one or more Y,
- or R3a and R4a, or R5a and R6a form a benzene ring, or
- wherein * is bonded to the carbon atom bonded to R3a, and ** is bonded to the carbon atom bonded to R4a, or * is bonded to the carbon atom bonded to R5a, and ** is bonded to the carbon atom bonded to R6a,
- R11a is selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, anthracenyl and phenanthrenyl, which may optionally be substituted with one or more Xa,
- R9a and R12a are each independently selected from the group consisting of hydrogen, and phenyl, 1-naphthyl, 2-naphthyl, anthracenyl and phenanthrenyl, which may optionally be substituted with one or more Xa,
- Xa is linear or branched C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, C1-6 alkoxy, halo, hydroxy, nitro, carboxy, cyano, sulfo, amino or alkylamino, which may optionally be substituted with one or more substituents selected from the group consisting of halo, amino, cyano, carboxy, carbonyl, hydroxy, alkoxy, alkylamino, nitroso, nitro and sulfo, and
- Y is selected from the group consisting of halo, amino, cyano, carboxy, carbonyl, alkoxy and sulfo, or
- having a structure of formula Ib or IIb:
- wherein
- R7b, R8b and R10b are each independently hydrogen, or linear or branched C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, C3-9 cycloalkyl, phenyl, 1-naphthyl, 2-naphthyl, anthracenyl or phenanthrenyl, which may optionally be substituted with one or more Xb,
- R3b, R4b, R5b and R6b are each independently hydrogen, or linear or branched C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, C1-6 alkoxy, halo, nitro, cyano, carboxy, sulfo or amino, which may optionally be substituted with one or more Y,
- R11b is selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, anthracenyl and phenanthrenyl, which may optionally be substituted with one or more Xb, wherein
- Xb is linear or branched C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, C1-6 alkoxy, halo, hydroxy, nitro, carboxy, cyano, sulfo or amino, which may optionally be substituted with one or more substituents selected from the group consisting of halo, amino, cyano, carboxy, carbonyl, alkoxy and sulfo, and
- Y is selected from the group consisting of halo, amino, cyano, carboxy, carbonyl, alkoxy and sulfo,
- or a salt, an anhydride or a solvate thereof,
- wherein the compound is neither N-methyl-N-phenyl-1,4-phenylenediamine, nor N-methyl-N-(3-methoxyphenyl)-1,4-phenylenediamine, and
- wherein the compound is neither
23 more elements
Dependencies are inferred from the claim text.