IP Library Granted Patent US 11,384,367
Granted Patent B2
US 11,384,367 · App. 16/450,824 · Granted Jul 12, 2022

Synthesis of bioproducts from lignin-derived aromatics by genetically modified microorganisms

Inventors: John M. Gladden (Alameda, CA); Jeffrey M. Skerker (Berkeley, CA); Jay D. Keasling (Berkeley, CA); James Kirby (Berkeley, CA); Junko Yaegashi (Hacienda Heights, CA)
Assignees: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; NATIONAL TECHNOLOGY AND ENGINEERING SOLUTIONS OF SANDIA, LLC; BATTELLE MEMORIAL INSTITUTE (FOR MANAGEMENT AND OPERATION OF PACIFIC NORTHWEST NATIONAL LABORATORY)
C12P1/02C07G1/00C08H6/00
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Quick Facts
Patent No.
US 11,384,367
App. No.
16/450,824
Granted
Jul 12, 2022
Kind
B2
Abstract

The present invention provides for a method of converting a depolymerized lignin aromatic compound into a bioproduct, comprising: (a) providing a composition comprising a depolymerized lignin aromatic compound, optionally a depolymerized cellulose, and optionally a depolymerized hemicellulose, and (b) introducing a genetically modified microorganism to the composition, wherein the genetically modified microorganism is capable of converting the depolymerized lignin aromatic compound into a bioproduct; such that the depolymerized lignin aromatic compound is converted into a bioproduct.

Claims (53)

1. A mixture of bioproducts produced by converting a mixture of depolymerized lignin aromatic compounds using a genetically modified microorganism capable of converting each depolymerized lignin aromatic compound into a bioproduct; wherein the mixture of depolymerized lignin aromatic compounds comprises:

(i) a mixture of depolymerized lignin aromatic compounds comprising the following chemical structures:

wherein R and R′ are each independently —H or —OCH 3 , and

wherein R, R′ and R″ are each independently —H, —OH, or —OCH 3 ,

(ii) a depolymerized lignin aromatic compound having the following chemical structure:

wherein R and R′ are each independently —H or —OCH 3 ,

(iii) a depolymerized lignin aromatic compound having the following chemical

wherein R and R′ are each independently —H or —OCH 3 and

(iv) an ionic liquid.

2. A composition comprising:

(a) (i) a mixture of depolymerized lignin aromatic compounds comprising the following chemical structures:

wherein R and R′ are each independently —H or —OCH 3 , and

wherein R, R′ and R″ are each independently —H, —OH, or —OCH 3 ,

(ii) a depolymerized lignin aromatic compound having the following chemical structure:

wherein R and R′ are each independently —H or —OCH 3 , and

(iii) a depolymerized lignin aromatic compound having the following chemical structure:

wherein R and R′ are each independently —H or —OCH 3 ,

(b) a depolymerized cellulose,

(c) a depolymerized hemicellulose,

(d) a genetically modified microorganism, wherein the genetically modified microorganism is capable of converting the depolymerized lignin aromatic compound into a bioproduct, and

(e) an ionic liquid.

3. The method of claim 2 , wherein the genetically modified microorganism is a fungal microorganism.

4. The method of claim 3 , wherein the fungal microorganism is of the genus Rhodotorula, Rhodosporidium , or Exophiala.

5. The method of claim 4 , wherein the fungal microorganism is Rhodotorula mucilaginosa, Rhodotorula graminis , or Rhodotorula glutinis.

6. The method of claim 3 , wherein the fungal microorganism is Rhodosporidium toruloides.

7. The method of claim 3 , wherein the fungal microorganism is Exophiala alcalophila.

8. The method of claim 2 , wherein the genetically modified microorganism is a bacterial microorganism.

9. The method of claim 8 , wherein the bacterial microorganism is of the genus Delftia or Rhodococcus.

10. The method of claim 9 , wherein the bacterial microorganism is Delftia acidovorans.

11. The method of claim 9 , wherein the bacterial microorganism is Rhodococcus rhodocorus.

12. A method of converting a depolymerized lignin aromatic compound into a bioproduct, comprising:

(a) providing a composition comprising

(i) a mixture of depolymerized lignin aromatic compounds comprising the following chemical structures:

 wherein R and R′ are each independently —H or —OCH 3 , and

 wherein R, R′ and R″ are each independently —H, —OH, or —OCH 3 ,

(ii) a depolymerized lignin aromatic compound having the following chemical structure:

 wherein R and R′ are each independently —H or —OCH 3 ,

(iii) a depolymerized lignin aromatic compound having the following

 wherein R and R′ are each independently —H or —OCH 3 , and

(iv) an ionic liquid, and

(b) introducing a genetically modified microorganism to the composition, wherein the genetically modified microorganism is capable of converting one of the depolymerized lignin aromatic compounds into a bioproduct;

such that the genetically modified microorganism converts a depolymerized lignin aromatic compound into the bioproduct.

13. The method of claim 1 , wherein the genetically modified microorganism is a fungal microorganism.

14. The method of claim 13 , wherein the fungal microorganism is of the genus Rhodotorula, Rhodosporidium , or Exophiala.

15. The method of claim 14 , wherein the fungal microorganism is Rhodotorula mucilaginosa, Rhodotorula graminis , or Rhodotorula glutinis.

16. The method of claim 14 , wherein the fungal microorganism is Rhodosporidium toruloides.

17. The method of claim 14 , wherein the fungal microorganism is Exophiala alcalophila.

18. The method of claim 1 , wherein the genetically modified microorganism is a bacterial microorganism.

19. The method of claim 18 , wherein the bacterial microorganism is of the genus Delftia or Rhodococcus.

20. The method of claim 19 , wherein the bacterial microorganism is Delftia acidovorans.

21. The method of claim 19 , wherein the bacterial microorganism is Rhodococcus rhodocorus.

22. The method of claim 1 , wherein the method further comprises contacting, prior to the providing step (a), a starting material with a depolymerization agent, wherein the starting material comprises a lignocellulosic biomass.

23. The method of claim 22 , wherein the depolymerization agent is NaOH, CuSO 4 , nitrobenzene, metal oxides, oxygen, a metal organic framework of Cu 2+ or Fe 3+ , ammonium hydroxide, hydrogen peroxide, Fenton's reagent, tetralin, sodium formate, or formic acid, or imidazolium ionic liquid.

Assignments (4)
CONFIRMATORY LICENSE Recorded May 1, 2020
From: UNIVERSITY OF CALIF-LAWRENC BERKELEY LAB
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 052545/0547 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2019
From: YAEGASHI, JUNKO
To: BATTELLE MEMORIAL INSTITUTE (FOR MANAGEMENT AND OPERATION OF PACIFIC NORTHWEST NATIONAL LABORATORY)
Reel/Frame 049580/0964 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2019
From: SKERKER, JEFFREY M.; KEASLING, JAY D.; KIRBY, JAMES
To: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
Reel/Frame 049581/0091 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2019
From: GLADDEN, JOHN M.
To: NATIONAL TECHNOLOGY & ENGINEERING SOLUTIONS OF SANDIA, LLC
Reel/Frame 049586/0533 →
Continuity (3)
Continuation PCTUS2017067737 · Dec 20, 2017
Provisional Application 62438434 · Dec 22, 2016
Related Publication 20190330663A1 · Oct 31, 2019