CONVERSION OF PRENYL DERIVATIVES TO ISOPRENE

• US 20100113846A1
• Filed: 09/15/2009
• Published: 05/06/2010
• Est. Priority Date: 09/15/2008
• Status: Active Grant

• Current Assignee: Goodyear Tire & Rubber Company
• Original Assignee: Goodyear Tire & Rubber Company
• Inventors: Rathnayake, Samira, Sanford, Karl J., MCAULIFFE, Joseph C.
• Granted Patent: US 8,476,049 B2
• Time in Patent Office: Days
• US Class Current: 585/16
• CPC Class Codes: C07C 1/2078 by a transformation in which at least one -C(=O)-O- moiety is eliminated
• CPC Class Codes: C07C 1/24 by elimination of water
• CPC Class Codes: C12N 9/14 Hydrolases (3)
• CPC Class Codes: C12N 9/16 acting on ester bonds (3.1)
• CPC Class Codes: C12N 9/88 Lyases (4.)
• CPC Class Codes: C12N 9/90 Isomerases (5.)
• CPC Class Codes: C12P 5/007 containing one or more isoprene units, i.e. terpenes carotenes C12P23/00
• CPC Class Codes: C12Y 301/03 Phosphoric monoester hydrolases (3.1.3)
• CPC Class Codes: C12Y 301/07 Diphosphoric monoester hydrolases (3.1.7)
• CPC Class Codes: C12Y 306/01 in phosphorus-containing anhydrides (3.6.1)
• CPC Class Codes: C12Y 503/03002 Isopentenyl-diphosphate DELTA-isomerase (5.3.3.2)

Abstract

The present invention provides methods for producing derivatives from cultured cells. In addition, the present invention provides methods for conversion of prenyl deerivatives, obtained from biological or petrochemical sources, to isoprene by employing chemical or biological catalysts. The present invention also provides compositions that include the cultured cells or isoprene or prenyl derivatives produced there from.

Claims

1. A method of producing isoprene, the method comprising

(a) culturing cells under suitable culture conditions for the production of a prenyl derivative of Formula (I):

2. The method of claim 1, wherein the prenyl derivative is prenyl alcohol.

3. The method of claim 1, wherein the prenyl derivative is recovered from a fermentation of the cultured cells using one or more processes selected from the group consisting of distillation, gas-stripping, two-phase recovery, and pervaporation.

4. The method of claim 2, wherein the process for recovering prenyl alcohol from a fermentation broth of the cultured cells comprises gas-stripping.

5. The method of claim 2, wherein process for recovering prenyl alcohol from a fermentation of the cultured cells comprises two-phase recovery.

6. The method of claim 1, wherein the prenyl derivative comprises one or more of prenol, isoprenol, 3-methyl-3-buten-1-yl acetate, and 3-methyl-2-buten-1-yl acetate.

7. The method of claim 1, wherein the cells further comprise one or more of an IDI polypeptide, an MVA pathway enzyme, and a DXP pathway enzyme.

8. The method of claim 1, wherein the cells further comprise prenol kinase activity.

9. The method of claim 1, wherein a catalyst selected from the group consisting of an inorganic acid catalyst, HCl, HBr, H₂SO₄, H₃PO₄, a solid acid catalyst, and inorganic acid on an inert carrier, activated alumina, a zeolite, and organic acid catalyst, p-toluenesulfonic acid, trifluoromethane sulfonic acid, an organic acid resin, Nafion, and a fluorosulfonic acid resin is used for dehydrating or decarboxylating said prenyl derivative to produce isoprene.

28. The method of claim 1, wherein the cells further comprise prenol kinase activity, an IDI polypeptide, and an isoprene synthase.

34. A composition comprising isoprene produced by the method of any one of claims 1, 10, 16, and 22.

10. A method of producing isoprene, the method comprising

(a) culturing cells under suitable culture conditions for the production of a prenyl derivative of Formula (II):

11. The method of claim 10, wherein the prenyl derivative is recovered from a fermentation of the cultured cells using one or more processes selected from the group consisting of distillation, gas-stripping, two-phase recovery, and pervaporation.

12. The method of claim 10, wherein the prenyl derivative comprises 2-methyl-3-buten-2-ol.

13. The method of claim 10, wherein the cells further comprise one or more of an IDI polypeptide, an MVA pathway enzyme, and a DXP pathway enzyme.

14. The method of claim 10, wherein the cells further comprise prenol kinase activity.

15. The method of claim 10, wherein a catalyst selected from the group consisting of an inorganic acid catalyst, HCl, HBr, H₂SO₄, H₃PO₄, a solid acid catalyst, and inorganic acid on an inert carrier, activated alumina, a zeolite, and organic acid catalyst, p-toluenesulfonic acid, trifluoromethane sulfonic acid, an organic acid resin, Nafion, and a fluorosulfonic acid resin is used for dehydrating or decarboxylating said prenyl derivative to produce isoprene.

29. The method of claim 10, wherein the cells futher comprise prenol kinase activity, an IDI polypeptide, and an isoprene synthase.

16. A method of producing isoprene, the method comprising

(a) culturing cells in culture medum under suitable culture conditions for the production of isoprene;

wherein said culture medium comprises a prenyl derivative of Formula (I);

17. The method of claim 16, wherein the cells are bacterial cells or yeast cells.

18. The method of claim 16, wherein the cells are selected from the group consisting of E. coli, P. citrea, B. subtilis, T. reesei, Y. lipolytica, and S. cerevisiae.

19. The method of claim 16, wherein the prenyl derivative comprises one or more of prenol, isoprenol, 3-methyl-3-buten-1-yl acetate, and 3-methyl-2-buten-1-yl acetate.

20. The method of claim 16, wherein the cells further comprise one or more of an IDI polypeptide, an MVA pathway enzyme, and a DXP pathway enzyme.

21. The method of claim 16, wherein the cells further comprise prenol kinase activity.

30. The method of claim 16, wherein the cells futher comprise prenol kinase activity, an IDI polypeptide, and an isoprene synthase.

32. The method of claim 16, wherein the cells produce isoprene at a rate of 0.1±

10 g/L/hour.

22. A method of producing isoprene, the method comprising

(a) culturing cells in culture medum under suitable culture conditions for the production of isoprene;

wherein said culture medium comprises a prenyl derivative of Formula (II);

23. The method of claim 22, wherein the cells are bacterial cells or yeast cells.

24. The method of claim 22, wherein the cells are selected from the group consisting of E. coli, P. citrea, B. subtilis, T. reesei, Y. lipolytica, and S. cerevisiae.

25. The method of claim 22, wherein the prenyl derivative comprises 2-methyl-3-buten-2-ol.

26. The method of claim 22, wherein the cells further comprise one or more of an IDI polypeptide, an MVA pathway enzyme, and a DXP pathway enzyme.

27. The method of claim 22, wherein the cells further comprise prenol kinase activity.

31. The method of claim 22, wherein the cells futher comprise prenol kinase activity, an IDI polypeptide, and an isoprene synthase.

33. The method of claim 22, wherein the cells produce isoprene at a rate of 0.1±

10 g/L/hour.