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Method for producing 4-aminocinnamic acid, and vector and host cell used in same

外国特許コード F210010535
整理番号 J1006-05WO
掲載日 2021年8月2日
出願国 欧州特許庁(EPO)
出願番号 19761067
公報番号 3760723
出願日 平成31年3月4日(2019.3.4)
公報発行日 令和3年1月6日(2021.1.6)
国際出願番号 JP2019008482
国際公開番号 WO2019168203
国際出願日 平成31年3月4日(2019.3.4)
国際公開日 令和元年9月6日(2019.9.6)
優先権データ
  • 特願2018-037794 (2018.3.2) JP
  • 2019JP08482 (2019.3.4) WO
発明の名称 (英語) Method for producing 4-aminocinnamic acid, and vector and host cell used in same
発明の概要(英語) Provided is a novel method for producing 4-aminocinnamic acid from 4-nitrophenylalanine. This method comprises: (1) converting 4-nitrophenylalanine into 4-nitrocinnamic acid; and (2) converting 4-nitrocinnamic acid into 4-aminocinnamic acid.
従来技術、競合技術の概要(英語) BACKGROUND
Concerns over exhaustion of petroleum resources and the issue of carbon dioxide emissions have increased the importance of systems for producing fuel and chemical products using biomass, which is a renewable resource. While examples of biomass-derived polymers include aliphatic polymers and aromatic polymers, research and development are currently progressing mainly on aliphatic polymers such as polylactic acid. Polylactic acid has been challenged by low heat resistance and durability, but this problem is being solved by, e.g., improvement in crystallinity. On the other hand, aromatic polymers often exhibit excellent material properties in terms of thermal stability and mechanical strength, and are expected to be used as raw materials for engineering plastics.
Of particular interest as a raw material monomer for biomass-derived aromatic polymers is 4-aminocinnamic acid. Patent Document 1 and Non-Patent Document 1, for example, report a method for synthesizing an aromatic polymer excellent in high heat resistance using 4-aminocinnamic acid as a raw material. Accordingly, there is a demand for a method of synthesizing 4-aminocinnamic acid from biomass with high efficiency, as a raw material monomer of such a high heat-resistance polymer.
The present inventors have developed a method for synthesizing 4-aminocinnamic acid from glucose in biomass using microbial-derived enzymes along a route wherein glucose is first converted to chorismic acid, then to 4-aminophenylpyruvate, and finally to 4-aminophenylalanine (Patent Document 2), which 4-aminophenylalanine is then converted to 4-aminocinnamic acid (Patent Document 3).
特許請求の範囲(英語) [claim1]
1. A method for producing 4-aminocinnamic acid from 4-nitrophenylalanine, comprising the steps of:
(1) converting 4-nitrophenylalanine to 4-nitrocinnamic acid; and
(2) converting 4-nitrocinnamic acid to 4-aminocinnamic acid.

[claim2]
2. The method according to claim 1, wherein the conversion of step (1) is carried out by using a first enzyme which has an amino acid sequence having a sequence homology of 80% or more to an amino acid sequence shown in SEQ ID NOs: 1, 3, or 5 and which has the ability to convert 4-nitrophenylalanine to 4-nitrocinnamic acid.

[claim3]
3. The method according to claim 2, wherein the conversion of step (1) is carried out with a first host cell which has been engineered to express the first enzyme.

[claim4]
4. The method according to claim 3, wherein the first host cell is a microorganism cell.

[claim5]
5. The method according to claim 4, wherein the microorganism is a bacterium.

[claim6]
6. The method according to claim 5, wherein the conversion of step (1) is carried out via a resting-cell reaction using a resting bacterial cell as the first host cell.

[claim7]
7. The method according to any one of claims 1 to 6, wherein the conversion of step (2) is carried out by using a second enzyme which has an amino acid sequence having a sequence homology of 80% or more to an amino acid sequence shown in SEQ ID NOs:7, 9, 11, 13, or 15 and which has the ability to convert 4-nitrocinnamic acid to 4-aminocinnamic acid.

[claim8]
8. The method according to claim 7, wherein the conversion of step (2) is carried out by using a second host cell which expresses the second enzyme.

[claim9]
9. The method according to claim 8, wherein the second host cell is a host cell engineered to express the second enzyme.

[claim10]
10. The method according to claim 8 or 9, wherein the second host cell is a microorganism cell.

[claim11]
11. The method according to claim 10, wherein the microorganism is a bacterium.

[claim12]
12. The method according to claim 11, wherein the conversion of step (2) is carried out via a resting-cell reaction using a resting bacterial cell as the second host cell.

[claim13]
13. The method according to claim 6 or 12, wherein the resting bacterial cell is selected from the group consisting of cultured cells, powdered cells, and immobilized cells.

[claim14]
14. The method according to any one of claims 7 to 13, wherein the conversion of step (2) is carried out at a pH of from 8 to 9.

[claim15]
15. A method for producing 4-aminocinnamic acid from glucose, comprising the steps of:
(a) producing phenylalanine from glucose;
(b) converting the phenylalanine obtained in step (a) to 4-nitrophenylalanine via nitration; and
(c) producing 4-aminocinnamic acid from the 4-nitrophenylalanine obtained in step (b) via a method according to any one of claims 1 to 14.

[claim16]
16. A method for producing 4-aminocinnamic acid from phenylalanine, comprising the steps of:
(b) converting phenylalanine to 4-nitrophenylalanine via nitration; and
(c) producing 4-aminocinnamic acid from the 4-nitrophenylalanine obtained in step (b) via a method according to any one of claims 1 to 14.

[claim17]
17. A method for producing 4-nitrocinnamic acid from 4-nitrophenylalanine, comprising:
using a first enzyme which has an amino acid sequence having a sequence homology of 80% or more to an amino acid sequence shown in SEQ ID NOs: 1, 3, or 5 and which has the ability to convert 4-nitrophenylalanine to 4-nitrocinnamic acid.

[claim18]
18. A method for producing 4-aminocinnamic acid from 4-nitrocinnamic acid, comprising:
using a second enzyme which has an amino acid sequence having a sequence homology of 80% or more to an amino acid sequence shown in SEQ ID NOs:7, 9, 11, 13, or 15 and which has the ability to convert 4-nitrocinnamic acid to 4-aminocinnamic acid.

[claim19]
19. A vector carrying a nucleic acid encoding a first enzyme which has an amino acid sequence having a sequence homology of 80% or more to an amino acid sequence shown in SEQ ID NOs: 1, 3, or 5 and which has the ability to convert 4-nitrophenylalanine to 4-nitrocinnamic acid.

[claim20]
20. A vector carrying a nucleic acid encoding a second enzyme which has an amino acid sequence having a sequence homology of 80% or more to an amino acid sequence shown in SEQ ID NOs:7, 9, 11, 13, or 15 and which has the ability to convert 4-nitrocinnamic acid to 4-aminocinnamic acid.

[claim21]
21. A host cell engineered to express a first enzyme which has an amino acid sequence having a sequence homology of 80% or more to an amino acid sequence shown in SEQ ID NOs: 1, 3, or 5 and which has the ability to convert 4-nitrophenylalanine to 4-nitrocinnamic acid.

[claim22]
22. A host cell engineered to express a second enzyme which has an amino acid sequence having a sequence homology of 80% or more to an amino acid sequence shown in SEQ ID NOs:7, 9, 11, 13, or 15 and which has the ability to convert 4-nitrocinnamic acid to 4-aminocinnamic acid.
  • 出願人(英語)
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • 発明者(英語)
  • TAKAYA NAOKI
  • MASUO SHUNSUKE
  • KAWASAKI YUKIE
  • MINAKAWA HAJIME
国際特許分類(IPC)
指定国 Contracting States: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
Extension States: BA ME
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