IP Library Granted Patent US 10,724,058
Granted Patent B2
US 10,724,058 · App. 15/817,493 · Granted Jul 28, 2020

Process for the biological production of methacrylic acid and derivatives thereof

Inventors: Graham Ronald Eastham (Redcar, GB); Gill Stephens (Nottingham, GB); Andrew Yiakoumetti (Nottingham, GB)
Assignee: LUCITE INTERNATIONAL UK LIMITED
C12P7/40C07C67/00C08F120/06C08F120/14C12N9/001C12N9/1029C12N9/16C12P5/026C12P7/62C12Y103/03006C12Y203/01084C12Y301/02023Y02E50/343
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 10,724,058
App. No.
15/817,493
Granted
Jul 28, 2020
Kind
B2
Abstract

A process of producing methacrylic acid and/or derivatives thereof including the following steps: (a) biologically converting isobutyryl-CoA into methacrylyl-CoA by the action of an oxidase; and (b) converting methacrylyl-CoA into methacrylic acid and/or derivatives thereof. The invention also extends to microorganisms adapted to conduct the steps of the process.

Claims (36)

1. A recombinant microorganism adapted to conduct the following steps:

(a) biologically converting isobutyryl-CoA into methacrylyl-CoA by expression of an oxidase, wherein the oxidase is an acyl-CoA that is ACX4 from Arabidopsis thaliana ; and

(b) biologically converting methacrylyl-CoA into methacrylic acid;

wherein the recombinant microorganism is Escherichia coli.

2. A microorganism modified by one or more heterologous nucleic acids to conduct the following steps:

(a) biologically converting isobutyryl-CoA into methacrylyl-CoA by expression of an oxidase, wherein the oxidase is an acyl-CoA that is ACX4 from Arabidopsis thaliana ; and

(b) biologically converting methacrylyl-CoA into methacrylic acid.

3. A microorganism adapted to conduct the following steps:

(a) biologically converting isobutyryl-CoA into methacrylyl-CoA by expression of an oxidase, wherein the oxidase is an acyl-CoA that is ACX4 from Arabidopsis thaliana ; and

(b) biologically converting methacrylyl-CoA into methacrylic acid and/or derivatives thereof.

4. A microorganism according to claim 3 , wherein the derivatives thereof of methacrylic acid are methacrylic acid esters, more preferably C1 to C20 alkyl esters, most preferably, C1 to C12 alkyl esters, especially C1 to C4 alkyl esters or C4 to C12 alkyl esters.

5. The microorganism according to claim 4 , wherein the microorganism expresses the following enzymes:

(a) (i) ACX4 from Arabidopsis thaliana ; and one or more of:

(b)(i) an acyl-CoA thioesterase; (ii) a CoA transferase; (iii) an acid-thiol synthetase; (iv) a phosphotransacylase and a short chain fatty acid kinase; (v) an alcohol acyltransferase.

6. The microorganism according to claim 3 , wherein the microorganism expresses the following enzymes:

(a) ACX4 from Arabidopsis thaliana ; and

(b) an acyl-CoA thioesterase.

7. The microorganism according to claim 3 , wherein the microorganism expresses the following enzymes:

(a) ACX4 from Arabidopsis thaliana ; and

(b) 4HBT.

8. A microorganism adapted to conduct the following steps:

(a) biologically converting isobutyryl-CoA into methacrylyl-CoA by expression of an acyl-CoA oxidase that is ACX4 from Arabidopsis thaliana ; and

(b) biologically converting methacrylyl-CoA into a C1 to C20 methacrylic acid ester, by expression of an alcohol acyl transferase.

9. A microorganism according to claim 8 , wherein the microorganism is Escherichia coli.

10. A microorganism according to claim 8 , wherein the microorganism is a recombinant microorganism.

11. The microorganism according to claim 6 , wherein the acyl-CoA thioesterase is 4HBT.

12. The microorganism according to claim 7 , wherein the 4HBT is from Arthrobacter sp.

13. A microorganism adapted to conduct the following steps:

(a) biologically converting isobutyryl-CoA into methacrylyl-CoA by the action of an oxidase, wherein the oxidase is an acyl-CoA that is ACX4 from Arabidopsis thaliana ; and

(b) biologically converting methacrylyl-CoA into methacrylic acid by the action of a thioesterase, transferase, synthetase, and/or a phosphotransacylase and a short chain fatty acid kinase.

14. The microorganism of claim 13 , wherein the thioesterase is a 4-hydroxybenzoyl-CoA thioesterase (4HBT).

15. A fermentation medium comprising one or more microorganisms of claim 3 .

16. A fermentation medium according to claim 3 , wherein the medium further comprises methacrylic acid and/or derivatives thereof.

17. A fermentation medium according to claim 3 , wherein the derivatives thereof of methacrylic acid are methacrylic acid esters, more preferably, C1 to C20 alkyl esters, most preferably, C1 to C12 alkyl esters, especially C1 to C4 alkyl esters or C4 to C12 alkyl esters.

18. A process of fermentation comprising culturing one or more microorganisms of claim 3 in a fermentation medium to produce methacrylic acid and/or derivatives thereof.

19. A process according to claim 3 wherein the derivatives thereof of methacrylic acid are methacrylic acid esters, more preferably, C1 to C20 alkyl esters, most preferably, C1 to C12 alkyl esters, especially C1 to C4 alkyl esters or C4 to C12 alkyl esters.

Assignments (2)
CHANGE OF NAME Recorded Jan 29, 2021
From: LUCITE INTERNATIONAL UK LIMITED
To: MITSUBISHI CHEMICAL UK LIMITED
Reel/Frame 055072/0175 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 22, 2018
From: EASTHAM, RONALD GRAHAM; STEPHENS, GILL; YIAKOUMETTI, ANDREW
To: LUCITE INTERNATIONAL UK LIMITED
Reel/Frame 045315/0682 →
Priority Claims (2)
GB 1508582.2 · May 19, 2015 · national
GB 1517545.8 · Oct 5, 2015 · national
Continuity (2)
Continuation 15574961
Related Publication 20180195095A1 · Jul 12, 2018