Reaction accelerating agent

Patent metadata

Field	Value
Publication number	US-11384381-B2
Application number	US-201716317216-A
Country	US
Kind code	B2
Filing date	Jul 13, 2017
Priority date	Jul 13, 2016
Publication date	Jul 12, 2022
Grant date	Jul 12, 2022

Abstract

Provided is a compound which accelerates the enzymatic reaction catalyzed by an oxidase. The present invention provides an oxidase reaction accelerating agent comprising a compound represented by formula (I) and a method using the same.

First claim

The invention claimed is:

1. A method comprising contacting an oxidase and a substrate for the oxidase with an oxidase reaction accelerating agent represented by the following formula (I):
[Formula 1]
R 1 —N═N—R 2 (I)
wherein
R 1 and R 2 are each independently an aromatic 5- or 6-membered monocyclic carbocyclic ring or heterocyclic ring containing at least one nitrogen atom, sulfur atom or oxygen atom, or a 9- or 10-membered fused ring containing the aromatic 5- or 6-membered monocyclic carbocyclic ring or heterocyclic ring, wherein the ring may optionally be substituted with one or more substituents, wherein
said substituent(s) is selected from the group consisting of —F, —Cl, —Br, —I, —At, —C 1-6 alkyl, —C 2-6 alkenyl, —C 2-6 alkynyl, ═O, —OH, —O—C 1-6 alkyl, —CONH 2 , —NO 2 , —NH 2 , —CO—NH 2 , —R 3 , —NH—R 4 , —NHCO—NH—R 5 —N═N—R 6 , —SO 3 X, —COOX, Y, and Z;
X is selected from the group consisting of —H, —Na, —K, and —Li;
Y is selected from the group consisting of —H, —SO 3 X, and —COOX;
Z is selected from the group consisting of —H, —C 1-6 alkyl, —O—C 1-6 alkyl, and —SO 3 X;
each X, Y, and Z may be the same or different;
—R 3 is —H, or is an aromatic 5- or 6-membered monocyclic carbocyclic ring or heterocyclic ring containing at least one nitrogen atom, sulfur atom or oxygen atom, or a 9- or 10-membered fused ring containing the aromatic 5- or 6-membered monocyclic carbocyclic ring or heterocyclic ring, wherein the ring may optionally be substituted with one or more substituents selected from the group consisting of —F, —Cl, —Br, —I, —At, —C 1-6 alkyl, —C 2-6 alkenyl, —C 2-6 alkynyl, ═O, —OH, —O—C 1-6 alkyl, —CONH 2 , —NO 2 , —NH 2 , and —SO 3 X;
—R 4 is an aromatic 5- or 6-membered monocyclic carbocyclic ring or heterocyclic ring containing at least one nitrogen atom, sulfur atom or oxygen atom, or a 9- or 10-membered fused ring containing the aromatic 5- or 6-membered monocyclic carbocyclic ring or heterocyclic ring, wherein the ring may optionally be substituted with one or more substituents selected from the group consisting of —F, —Cl, —Br, —I, —At, —C 1-6 alkyl, —C 2-6 alkenyl, —C 2-6 alkynyl, ═O, —OH, —O—C 1-6 alkyl, —CONH 2 , —NO 2 , —NH 2 , —SO 3 X, —COOX, Y, and Z; and
—R 5 and —R 6 are each independently an aromatic 5- or 6-membered monocyclic carbocyclic ring or heterocyclic ring containing at least one nitrogen atom, sulfur atom or oxygen atom, or a 9- or 10-membered fused ring containing the aromatic 5- to 6-membered monocyclic carbocyclic ring or heterocyclic ring, wherein the ring may optionally be substituted with one or more substituents selected from the group consisting of —F, —Cl, —Br, —I, —At, —C 1-6 alkyl, —C 2-6 alkenyl, —C 2-6 alkynyl, ═O, —OH, —O—C 1-6 alkyl, —O—CH 3 , —CONH 2 , —NO 2 , —NH 2 , —SO 3 X, —COOX, Y, and Z,
provided that when R 1 or R 2 is an aromatic 5-membered monocyclic carbocyclic ring or heterocyclic ring containing at least one nitrogen atom, sulfur atom or oxygen atom, the heterocyclic ring is not substituted with —COOX,
wherein when R 1 or R 2 is

then R 2 or R 1 , respectively, is not

wherein the compound represented by the following formula is excluded from the oxidase reaction accelerating agent of formula (I):

wherein, when R 1 or R 2 is

and R 2 or R′, respectively, is,

then the oxidase is an oxidase selected from the group consisting of sarcosine oxidase, and cholesterol oxidase;
wherein, when R 1 or R 2 is

and R 2 or R′, respectively, is

and wherein the Y which may be at positions 2, 3 or 4 of the 1-naphthyl group is H and the two Y groups which may be at positions 5, 6, 7 or 8 of the 1-naphthyl group are both —SO 3 X, then the oxidase is an oxidase selected from the group consisting of sarcosine oxidase, and cholesterol oxidase;
wherein, when R 1 or R 2 is

and R 2 or R′, respectively, is

and wherein the Y which may be at positions 2, 3 or 4 of the 1-naphthyl group is —SO 3 X and one of the Y groups which may be at positions 5, 6, 7 or 8 of the 1-naphthyl group is H and the other Y group which may be at positions 5, 6, 7 or 8 of the 1-naphthyl group is —SO 3 X, then the oxidase is an oxidase selected from the group consisting of sarcosine oxidase, and cholesterol oxidase;
wherein, when the oxidase reaction accelerating agent is represented by the following formula:

then the oxidase is an oxidase selected from the group consisting of amadoriase, sarcosine oxidase, and cholesterol oxidase,
wherein, when R 1 or R 2 is

and R 2 or R′, respectively is an aromatic 6-membered monocyclic carbocyclic ring substituted with —COOX, then the oxidase is an oxidase selected from the group consisting of amadoriase and sarcosine oxidase; and
wherein when the compound represented by Formula (I) is

then the oxidase is selected from the group consisting of amadoriase, sarcosine oxidase, and cholesterol oxidase.

2. The method according to claim 1 , wherein regarding the reaction accelerating agent represented by formula (I), R 1 and R 2 are each independently an aromatic 6-membered monocyclic carbocyclic ring, or a 10-membered fused ring containing the aromatic 6-membered monocyclic carbocyclic ring, wherein the ring may optionally be substituted with one or more substituents or wherein regarding the reaction accelerating agent represented by formula (I), R 1 and R 2 are each independently selected from the group consisting of

wherein X, Y, and Z are as defined in claim 1 .

3. The method according to claim 1 , wherein regarding the reaction accelerating agent represented by formula (I), R 1 is selected from the group consisting of

and R 1 is selected from the group consisting of

wherein X is as defined in claim 1 .

4. The method according to claim 1 , wherein the reaction accelerating agent represented by formula (I) is a reaction accelerating agent

Assignees

• Kikkoman Corp

Inventors

• Ichiyanagi Atsushi
• Shimoji Kazuhiko

Classifications

• C07C245/08

  with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene · CPC title

• C12Q1/26 Primary

  involving oxidoreductase · CPC title

• C12N15/09

  Recombinant DNA-technology · CPC title

• C07C309/49

  the carbon skeleton being further substituted by singly-bound oxygen atoms · CPC title

• C07C309/46

  having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings · CPC title