Method for producing 3-hydroxy-4-aminobenzoic acid compound

Patent metadata

Field	Value
Publication number	US-11312980-B2
Application number	US-201917269689-A
Country	US
Kind code	B2
Filing date	Sep 6, 2019
Priority date	Sep 13, 2018
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

Provided is a method for manufacturing a 3-hydroxy-4-aminobenzoic acid by using a microorganism. The method for manufacturing a 3-hydroxy-4-aminobenzoic acid comprises a step of bringing a 4-aminobenzoic acid into contact with a microorganism that produces the following polypeptide (A) or (B): (A) a polypeptide consisting of an amino acid sequence shown in SEQ ID NO: 2 or a polypeptide consisting of an amino acid sequence that has at least 90% identity to the amino acid sequence shown in SEQ ID NO: 2 and has 4-hydroxybenzoate hydroxylase activity, (B) a polypeptide consisting of an amino acid sequence shown in SEQ ID NO: 6 or a polypeptide consisting of an amino acid sequence that has at least 90% identity to the amino acid sequence shown in SEQ ID NO: 6 and has 4-hydroxybenzoate hydroxylase activity.

First claim

The invention claimed is:

1. A method for manufacturing a 3-hydroxy-4-aminobenzoic acid, comprising a step of bringing a 4-aminobenzoic acid into contact with a microorganism that produces polypeptide (A) or (B) shown below:
(A) a polypeptide consisting of the amino acid sequence of SEQ ID NO: 2 or a polypeptide consisting of an amino acid sequence that has at least 90% identity to the amino acid sequence of SEQ ID NO: 2 and has 4-hydroxybenzoate hydroxylase activity, or
(B) a polypeptide consisting the an amino acid sequence of SEQ ID NO: 6 or a polypeptide consisting of an amino acid sequence that has at least 90% identity to the amino acid sequence of SEQ ID NO: 6 and has 4-hydroxybenzoate hydroxylase activity.

2. The method of claim 1 , wherein the microorganism comprises the following polynucleotide (a) or (b) in an expressible state:
(a) a polynucleotide consisting of the nucleotide sequence of SEQ ID NO: 1 or a polynucleotide consisting of a nucleotide sequence that has at least 90% identity to the nucleotide sequence of SEQ ID NO: 1 and encodes a polypeptide having 4-hydroxybenzoate hydroxylase activity, or
(b) a polynucleotide consisting of the nucleotide sequence of SEQ ID NO: 5 or a polynucleotide consisting of a nucleotide sequence that has at least 90% identity to the nucleotide sequence of SEQ ID NO: 5 and encodes a polypeptide having 4-hydroxybenzoate hydroxylase activity.

3. The method of claim 2 , wherein the microorganism is Escherichia coli or Corynebacterium.

4. The method of claim 2 , wherein the 4-aminobenzoic acid is a 4-aminobenzoic acid derivative having Formula (1) shown below:

wherein R 1 is a hydrogen atom, a hydroxy group, a methoxy group, an amino group, a fluorine atom, a chlorine atom, a bromine atom, a iodine atom, a carboxy group, a methyl group, or an ethyl group; and R 2 is a hydrogen atom, a hydroxy group, a methoxy group, an amino group, a fluorine atom, a chlorine atom, a bromine atom, a iodine atom, a carboxy group, a methyl group, or an ethyl group, and the 3-hydroxy-4-aminobenzoic acid is a 3-hydroxy-4-aminobenzoic acid derivative having Formula (2) shown below:

wherein R 1 and R 2 are the same as above; and one of the Xs is a hydrogen atom, and the other X is a hydroxy group.

5. The method of claim 2 , wherein the contact between the 4-aminobenzoic acid and the microorganism is carried out by bringing a cell homogenate of the microorganism into contact with the 4-aminobenzoic acid at from 20° C. to 50° C., for from 5 minutes to 72 hours.

6. The method of claim 1 , wherein the microorganism is Escherichia coli or Corynebacterium.

7. The method of claim 6 , wherein the 4-aminobenzoic acid is a 4-aminobenzoic acid derivative having Formula (1) shown below:

wherein R 1 is a hydrogen atom, a hydroxy group, a methoxy group, an amino group, a fluorine atom, a chlorine atom, a bromine atom, a iodine atom, a carboxy group, a methyl group, or an ethyl group; and R 2 is a hydrogen atom, a hydroxy group, a methoxy group, an amino group, a fluorine atom, a chlorine atom, a bromine atom, a iodine atom, a carboxy group, a methyl group, or an ethyl group, and the 3-hydroxy-4-aminobenzoic acid is a 3-hydroxy-4-aminobenzoic acid derivative having Formula (2) shown below:

wherein R 1 and R 2 are the same as above; and one of Xs is a hydrogen atom, and the other a hydroxy group.

8. The method of claim 6 , wherein the contact between the 4-aminobenzoic acid and the microorganism is carried out by bringing a cell homogenate of the microorganism into contact with the 4-aminobenzoic acid at from 20° C. to 50° C., for from 5 minutes to 72 hours.

9. The method of claim 1 , wherein the 4-aminobenzoic acid is a 4-aminobenzoic acid derivative having Formula (1) shown below:

wherein R 1 is a hydrogen atom, a hydroxy group, a methoxy group, an amino group, a fluorine atom, a chlorine atom, a bromine atom, a iodine atom, a carboxy group, a methyl group, or an ethyl group; and R 2 is a hydrogen atom, a hydroxy group, a methoxy group, an amino group, a fluorine atom, a chlorine atom, a bromine atom, a iodine atom, a carboxy group, a methyl group, or an ethyl group, and the 3-hydroxy-4-aminobenzoic acid is a 3-hydroxy-4-aminobenzoic acid derivative having Formula (2) shown below:

wherein R 1 and R 2 are the same as above; and one of the Xs is a hydrogen atom, and the other X is a hydroxy group.

10. The method of claim 9 , wherein in the 4-aminobenzoic acid derivative having Formula (1) and the 3-hydroxy-4-aminobenzoic acid derivative having Formula (2), le is a hydrogen atom, a hydroxy group, a methoxy group, a fluorine atom, or a methyl group.

11. The method of claim 9 , wherein in the 4-aminobenzoic acid derivative having Formula (1) and the 3-hydroxy-4-aminobenzoic acid derivative having Formula (2), R 2 is a hydrogen atom, a hydroxy group, a methoxy group, a fluorine atom, or a methyl group.

12. The method of claim 9 , wherein in the 4-aminobenzoic acid derivative having Formula (1) and the 3-hydroxy-4-aminobenzoic acid derivative having Formula (2), R 1 and R 2 are both hydrogen atoms.

13. The method of claim 1 , wherein the contact between the 4-aminobenzoic acid and the microorganism is carried out by bringing a cell homogenate of the microorganism into contact with the 4-aminobenzoic acid at from 20° C. to 50° C., for from 5 minutes to 72 hours.

Assignees

• Kao Corp

Inventors

• Nonaka Kyoshiro
• Takahashi Fumikazu

Classifications

• C12P13/001 Primary

  Amines; Imines · CPC title

• C12N15/09

  Recombinant DNA-technology · CPC title

• C12N9/0073

  with NADH or NADPH as one donor, and incorporation of one atom of oxygen 1.14.13 · CPC title

• C12P13/005 Primary

  Amino acids other than alpha- or beta amino acids, e.g. gamma amino acids · CPC title

• C12Y114/13002

  4-Hydroxybenzoate 3-monooxygenase (1.14.13.2) · CPC title