Compositions and methods for making and modifying oils

Patent metadata

Field	Value
Publication number	US-9243267-B2
Application number	US-201514615524-A
Country	US
Kind code	B2
Filing date	Feb 6, 2015
Priority date	Sep 10, 2004
Publication date	Jan 26, 2016
Grant date	Jan 26, 2016

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.

First claim

What is claimed is:

1. A method for generating one or more fatty acid species comprising
(a) providing an oil or a lipid comprising at least one species of fatty acid;
(b) providing a lipase that is at least 80% identical to the amino acid sequence as set forth in SEQ ID NO:1174, SEQ ID NO:1178, SEQ ID NO:1180, SEQ ID NO:1182 or SEQ ID NO:1184; and
(c) contacting the oil or lipid of (a) with the enzyme of (b) under conditions wherein the enzyme selectively hydrolyzes at least one fatty acid species molecule from the oil or lipid, thereby releasing the fatty acid species from the oil or lipid and generating the fatty acid species.

2. The method of or claim 1 , wherein the lipase hydrolyzes all of the fatty acid species in the oil or lipid, thereby producing an oil or lipid completely lacking the fatty acid species of (a).

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

4. The method of claim 3 , wherein the plant oil comprises a vegetable oil.

5. 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.

6. The method of claim 1 , wherein the lipid comprises a 5 glyceride, a glycolipid, a phospholipid, a sphingolipid, a coenzyme A, an oxidized lipid or an ether lipid.

7. The method of claim 1 , wherein the at least one species of fatty acid of step (a) is linoleic acid (cis-9, cis-12-octadecadienoic acid), linolenic acid, palmitic acid or stearic acid.

8. The method of claim 1 , wherein the at least one species of fatty acid of step (a) is a saturated fatty acid.

9. The method of claim 8 , wherein the saturated fatty acid is 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.

10. The method of claim 1 , wherein the at least one species of fatty acid of step (a) is a monoenoic fatty acid.

11. The method of claim 10 , wherein the monoenoic fatty acid is obtusilic acid, caproleic acid, lauroleic acid, linderic acid, myristoleic acid, physeteric acid, tsuzuic acid, palmitoleic acid, petroselinic acid or oleic acid.

12. The method of claim 1 , wherein the at least one species of fatty acid of step (a) is a polyenoic fatty acid (polyunsaturated fatty acid, or PUFA).

13. The method of claim 12 , wherein the polyenoic fatty acid is 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, a-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.

14. The method of claim 1 , wherein the at least one species of fatty acid of step (a) is 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.

15. The method of claim 1 , wherein the enzyme capable of selectively hydrolyzing the fatty acid species of (a) is a hydrolase, a lipase, a phospholipase, an esterase, an oxidoreductase, a chlorophyllase or a glycosidase.

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) fatty acid.

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

19. The method of claim 17 , wherein the hydrolyzed fatty acid is removed from the oil by a saponification reaction or use of a silica.

20. 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.

21. The method of claim 1 , wherein the provided enzyme specifically hydrolyzes fatty acids having various degrees of saturation.

22. The method of claim 1 , wherein the provided enzyme has mono-, di-, or triglyceride selectivity to fatty acids.

23. The method of claim 1 , wherein the provided enzyme has cis-versus trans-fatty acid specificity.

24. The method of claim 1 , wherein the provided enzyme has conjugated versus unconjugated fatty acid specificity.

25. The method of claim 1 , wherein the provided enzyme has fatty acid chain length specificity.

26. The method of claim 1 , wherein the provided enzyme specifically hydrolyzes oxidized lipids or non-oxidized lipids.

27. The method of claim 1 , wherein the provided enzyme has regioselective catalytic activity.

28. The method of claim 27 , wherein the regioselective catalytic activity comprises selective Sn-1 versus Sn-2 versus Sn-3 reactivity.

29. The method of claim 1 , wherein the provided enzyme has positionally selective catalytic activity.

Assignees

• Dsm Ip Assets Bv

Inventors

• Lam David
• Weiner David
• Hitchman Tim S
• Barton Nelson R
• Lyon Jonathan D

Classifications

• C12P7/6418 Primary

  by hydrolysis of fatty acid esters · CPC title

• Y02E50/10

  Biofuels, e.g. bio-diesel · CPC title

• C12P7/6454

  by esterification · CPC title

• C12P7/6472

  containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone · CPC title

• C12P7/6481

  Phosphoglycerides (phosphoglycerides having carboxylic acids with less than seven carbon atoms C12P7/62) · CPC title