Conversion of prenyl derivatives to isoprene

• US 8,945,893 B2
• Filed: 06/06/2013
• Issued: 02/03/2015
• Est. Priority Date: 09/15/2008
• Status: Expired due to Fees

• Current Assignee: Goodyear Tire & Rubber Company
• Original Assignee: Goodyear Tire & Rubber Company, Danisco USA Incorporated (International Flavors & Fragrances Incorporated)
• Inventors: McAuliffe, Joseph C., Rathnayake, Samira, Sanford, Karl J.
• Primary Examiner(s): Kosson, Rosanne
• Application Number:
  US13/912,002
• Publication Number:
  US 20130309743A1
• Time in Patent Office: 607 Days
• Field of Search: 435/167, 435/196, 435/195
• US Class Current: 435/167
• 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 derivatives, 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 host cells comprising one or more nucleic acid(s) encoding one or more phosphatases of enzyme class 3.6.1, 3.1.7 or 3.1.3 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 of the cultured cells comprises gas-stripping or two-phase recovery.

5. 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.

6. The method of claim 1, wherein the cells further comprise one or more of an isopentenyl-diphosphate-delta-isomerase (IDI) polypeptide, one or more mevalonic acid (MVA) pathway polypeptides, and/or one or more deoxyxylulose-5-phosphate (DXP) pathway polypeptides.

7. The method of claim 1, wherein the cells further comprise one or more lower MVA pathway polypeptides.

8. The method of claim 1, wherein the one or more phosphatases of enzyme class 3.6.1, 3.1.7 or 3.1.3 are one or more phosphatases selected from the group consisting of an allyl diphosphatase, an ADP-ribose pyrophosphatase, an ADP-sugar phosphorylase, a nucleoside triphosphate pyrophosphatase, a FAD pyrophosphatase, a monoterpenyl pyrophosphastase, an alkaline phosphatase, and an acid phosphatase.

9. The method of claim 1, wherein the dehydration or decarboxylation reaction of step (c) comprises contacting the compound of Formula (I) with an inorganic or organic catalyst.

10. The method of claim 9, wherein the inorganic catalyst is selected from the group consisting of HCl, HBr, H₂SO₄, H₃PO₄, a solid acid catalyst, an inorganic acid on an inert carrier, an activated alumina, and a zeolite.

11. The method of claim 9, wherein the organic catalyst is selected from the group consisting of p-toluenesulfonic acid, trifluoromethane sulfonic acid, an organic acid resin, a Nafion, and a fluorosulfonic acid resin.