Compositions and methods for making and modifying oils

• US 9,034,612 B2
• Filed: 05/24/2013
• Issued: 05/19/2015
• Est. Priority Date: 09/10/2004
• Status: Expired due to Fees

• Current Assignee: DSM IP Assets BV (DSM-Firmenich AG)
• Original Assignee: DSM IP Assets BV (DSM-Firmenich AG)
• Inventors: Lam, David, Weiner, David, Hitchman, Tim S., Barton, Nelson R., Lyon, Jonathan D.
• Primary Examiner(s): Saidha, Tekchand
• Application Number:
  US13/902,739
• Publication Number:
  US 20140193866A1
• Time in Patent Office: 725 Days
• Field of Search: 435/134
• US Class Current: 435/134
• CPC Class Codes: C12P 7/6418 by hydrolysis of fatty acid esters
• CPC Class Codes: C12P 7/6427 Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone
• CPC Class Codes: C12P 7/6431 Linoleic acids [18:2[n-6]]
• CPC Class Codes: C12P 7/6432 Eicosapentaenoic acids [EPA]
• CPC Class Codes: C12P 7/6434 Docosahexenoic acids [DHA]
• CPC Class Codes: C12P 7/6454 by esterification
• CPC Class Codes: C12P 7/6458 by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
• CPC Class Codes: C12P 7/6472 containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
• CPC Class Codes: C12P 7/6481 Phosphoglycerides phosphoglycerides having carboxylic acids with less than seven carbon atoms C12P7/62
• CPC Class Codes: C12P 7/649 Biodiesel, i.e. fatty acid alkyl esters
• CPC Class Codes: Y02E 50/10 Biofuels, e.g. bio-diesel

Abstract

The invention provides novel methods for making or modifying oils, e.g., plant animal or microbial oils, such as vegetable oils or related compounds, that are low in a particular fatty acid(s), for example, low linoleic oils, linolenic oils, low palmitic oils, low stearic oils or oils low in a combination thereof.

Claims

1. A method for making an oil or a lipid low in palmitic and/or linolenic acid comprising

(a) providing an oil or a lipid comprising at least one palmitic and/or linolenic acid;

(b) providing an enzyme encoded by a polynucleotide as set forth in the full length nucleic acid sequence of SEQ ID NO;

1163, wherein the enzyme is capable of selectively hydrolyzing (releasing) one or more palmitic and/or linolenic acid of (a) from the oil or lipid; and

(c) contacting the oil or lipid of (a) with the enzyme of (b) under conditions wherein the enzyme selectively hydrolyzes at least one palmitic and/or linolenic acid molecule, thereby making an oil or a lipid having at least one fewer palmitic and/or linolenic acid molecule.

3. The method of claim 1, wherein the enzyme hydrolyzes all of the palmitic and/or linolenic acid in the oil or lipid, thereby producing an oil or lipid completely lacking the palmitic and/or linolenic acid of (a).

4. The method of claim 1, wherein the oil comprises a plant oil, an animal oil or a microbial oil.

5. The method of claim 4, wherein the plant oil comprises a vegetable oil.

6. The method of claim 1, wherein the oil is derived from a plant oil, a high phosphorous oil, a soy oil, a canola oil, a palm oil, a cottonseed oil, a corn oil, a palm kernel-derived oil, a rice bran oil, a coconut oil, a peanut oil, a sesame oil, a fish oil, an algae oil, a sunflower oil, an essential oil, a fruit seed oil, a grapeseed oil, an apricot oil, or a borage oil.

7. The method of claim 1, wherein the lipid comprises a glyceride, a glycolipid, a phospholipid, a sphingolipid, a coenzyme A, an oxidized lipid or an ether lipid.

8. The method of claim 1, wherein the at least one palmitic and/or linolenic acid of step (a) is linoleic acid (cis-9, cis-12-octadecadienoic acid), linolenic acid, or palmitic acid.

9. The method of claim 1, wherein the at least one palmitic and/or linolenic acid of step (a) is a saturated fatty acid.

10. The method of claim 9, wherein the saturated fatty acid is palmitic acid.

11. The method of claim 1, wherein the at least one palmitic and/or linolenic acid of step (a) is a polyenoic fatty acid (polyunsaturated fatty acid, or PUFA).

12. The method of claim 11, wherein the polyenoic fatty acid is linoleic acid, γ

-linolenic acid, dihomo-γ

-linolenic acid, or γ

-linolenic acid (9,12,15-octadecatrienoic acid).

13. The method of claim 1, wherein the enzyme capable of selectively hydrolyzing the fatty acid species of (a) is a lipase.

14. The method of claim 1, wherein the enzyme encoded by a polynucleotide as set forth in the full length nucleic acid sequence of SEQ ID NO:

1163 capable of selectively hydrolyzing the palmitic and/or linolenic acid is a polypeptide comprising an amino acid sequence having at least 95%, 96%, 97%, 98%, 99%, or greater sequence identity over the full length to SEQ ID NO;

1164.

15. The method of claim 1, wherein contacting conditions comprise higher water conditions for the selective hydrolysis reaction.

16. The method of claim 1, wherein contacting conditions comprise reaction conditions comprising a pH in the range of about 4 to about 10.

17. The method of claim 1, further comprising removing from the oil the hydrolyzed (released) palmitic and/or linolenic acid.

18. The method of claim 17, wherein the hydrolyzed palmitic and/or linolenic acid is removed from the oil by steam distillation.

19. The method of claim 1, wherein the enzyme is added to the oil before, during or after a degumming step, or any combination thereof.

20. The method of claim 17, wherein the hydrolyzed palmitic and/or linolenic acid is removed from the oil by a saponification reaction or use of a silica.

21. The method of claim 1, wherein the oil or lipid of (a) is comprises a waste stream, a restaurant grease, an animal processing by-product, an animal feed bypass fat, or an impure or mixed source of plant, animal, microbial oil.

22. The method of claim 1, wherein the provided enzyme specifically hydrolyzes palmitic and/or linolenic acids having various degrees of saturation.

25. The method of claim 1, wherein the oil or the glyceride further comprises:

a glycolipid, a phospholipid, a sphingolipid, a coenzyme A, an oxidized lipid or an ether lipid, a linoleic acid (cis-9, cis-12-octadecadienoic acid), a linolenic acid, a stearic acid, a saturated fatty acid, a fatty acid comprising a butyric acid, valeric acid, caproic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, margaric (daturic) acid, stearic acid, arachidic acid, behenic acid, lignoceric acid or cerotic acid, a monoenoic fatty acid;

a lipid comprising an obtusilic acid, caproleic acid, lauroleic acid, linderic acid, myristoleic acid, physeteric acid, tsuzuic acid, palmitoleic acid, petroselinic acid or oleic acid, a lipid comprising a polyenoic fatty acid (polyunsaturated fatty acid, or PUFA), a polyenoic fatty acid comprising an eicosapentaenoic acid, linoleic acid, γ

-linolenic acid, dihomo-γ

-linolenic acid, arachidonic acid, 7,10,13,16-docosatetraenoic acid, 4,7,10,13,16-docosapentaenoic acid, α

-linolenic acid (9,12,15-octadecatrienoic acid), stearidonic acid, 8,11,14,17-eicosatetraenoic acid, 5,8,11,14,17-eicosapentaenoic acid (EPA), 7,10,13,16,19-docosapentaenoic (DPA), 4,7,10,13,16,19-docosahexaenoic acid (DHA), or 5,8,11-eicosatrienoic, a branched chain fatty acid, a branched methoxy fatty acid, a ring-containing fatty acid, an acetylenic fatty acid, a hydroxy fatty acid, a fatty acid amide, a keto fatty acid, or a halogenated fatty acid.

2. A method for generating one or more palmitic and/or linolenic acid comprising

(a) providing an oil or a lipid comprising at least one palmitic and/or linolenic acid;

(b) providing an enzyme encoded by a polynucleotide as set forth in the full length nucleic acid sequence of SEQ ID NO;

1163, wherein the enzyme is capable of selectively hydrolyzing (releasing) one or more palmitic and/or linolenic acid of (a) oil or a lipid; and

(c) contacting the oil or lipid of (a) with the enzyme of (b) under conditions wherein the enzyme selectively hydrolyzes at least one palmitic and/or linolenic acid molecule from the oil or lipid, thereby releasing the palmitic and/or linolenic acid species from the oil or lipid and generating the palmitic and/or linolenic acid.

23. The method of claim 2, wherein the oil comprises a plant oil, an animal oil, or a microbial oil.

24. The method of claim 2, wherein the oil is derived from a plant oil, a high phosphorous oil, a soy oil, a canola oil, a palm oil, a cottonseed oil, a corn oil, a palm kernel-derived oil, a rice bran oil, a coconut oil, a peanut oil, a sesame oil, a fish oil, an algae oil, a sunflower oil, an essential oil, a fruit seed oil, a grapeseed oil, an apricot oil, or a borage oil.