Compositions and Methods for Making and Modifying Oils
First Claim
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1. A method for making an oil or a lipid low in a particular fatty acid species comprising(A) (a) providing an oil or a lipid comprising at least one specie of fatty acid;
- (b) providing an enzyme capable of selectively hydrolyzing (releasing) one or more particular fatty acid species 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 fatty acid species molecule, thereby making an oil or a lipid having at least one fewer fatty acid species molecule;
(B) the method of (A), wherein the enzyme 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);
(C) the method of (A) or (B), wherein the oil comprises a plant oil, an animal oil or a microbial oil, or a plant oil comprising a vegetable oil;
or an 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;
(D) the method of (A), (B) or (C), wherein the lipid comprises a glyceride, a glycolipid, a phospholipid, a sphingolipid, a coenzyme A, an oxidized lipid or an ether lipid, or the lipid comprises a linoleic acid (cis-9, cis-12-octadecadienoic acid), linolenic acid, palmitic acid or stearic acid;
or the lipid comprises a saturated fatty acid;
or the lipid comprises 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;
or the lipid comprises a monoenoic fatty acid;
or the lipid comprises an obtusilic acid, caproleic acid, lauroleic acid, linderic acid, myristoleic acid, physeteric acid, tsuzuic acid, palmitoleic acid, petroselinic acid or oleic acid;
or the lipid comprises a polyenoic fatty acid (polyunsaturated fatty acid, or PUFA);
or the lipid comprises an 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;
or the lipid comprises 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;
(E) the method of any of (A) to (D), 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;
(F) the method of any of (A) to (E), wherein contacting conditions comprise higher water conditions for the selective hydrolysis reaction;
(G) the method of any of (A) to (E), wherein contacting conditions comprise reaction conditions comprising a pH in the range of about 4 to about 10;
(H) the method of any of (A) to (G), further comprising removing from the oil the hydrolyzed (released) fatty acid;
(I) the method of any of (H), wherein the hydrolyzed fatty acid is removed from the oil by steam distillation;
(J) the method of any of (A) to (I), wherein the enzyme is added to the oil before, during or after a degumming step, or any combination thereof;
(K) the method of any of (A) to (J), wherein the hydrolyzed fatty acid is removed from the oil by a saponification reaction or use of a silica;
(L) the method of any of (A) to (K), 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;
(M) the method of any of (A) to (L), wherein the provided enzyme specifically hydrolyzes fatty acids having various degrees of saturation;
(N) the method of any of (A) to (M), wherein the provided enzyme has mono-, di-, or triglyceride selectivity to fatty acids;
(O) the method of any of (A) to (N), wherein the provided enzyme has cis- versus trans-fatty acid specificity;
(P) the method of any of (A) to (O), wherein the provided enzyme has conjugated versus unconjugated fatty acid specificity;
(Q) the method of any of (A) to (P), wherein the provided enzyme has fatty acid chain length specificity;
(R) the method of any of (A) to (O), wherein the provided enzyme specifically hydrolyzes oxidized lipids or non-oxidized lipids;
(S) the method of any of (A) to (T), wherein the provided enzyme has regioselective catalytic activity;
(T) the method of any of (A) to (S), wherein the regioselective catalytic activity comprises selective Sn-1 versus Sn-2 versus Sn-3 reactivity;
or(U) the method of any of (A) to (T), wherein the provided enzyme has positionally selective catalytic activity.
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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, low linolenic oils, low palmitic oils, low stearic oils or oils low in a combination thereof.
63 Citations
45 Claims
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1. A method for making an oil or a lipid low in a particular fatty acid species comprising
(A) (a) providing an oil or a lipid comprising at least one specie of fatty acid; -
(b) providing an enzyme capable of selectively hydrolyzing (releasing) one or more particular fatty acid species 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 fatty acid species molecule, thereby making an oil or a lipid having at least one fewer fatty acid species molecule; (B) the method of (A), wherein the enzyme 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); (C) the method of (A) or (B), wherein the oil comprises a plant oil, an animal oil or a microbial oil, or a plant oil comprising a vegetable oil;
or an 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;(D) the method of (A), (B) or (C), wherein the lipid comprises a glyceride, a glycolipid, a phospholipid, a sphingolipid, a coenzyme A, an oxidized lipid or an ether lipid, or the lipid comprises a linoleic acid (cis-9, cis-12-octadecadienoic acid), linolenic acid, palmitic acid or stearic acid;
or the lipid comprises a saturated fatty acid;
or the lipid comprises 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;
or the lipid comprises a monoenoic fatty acid;
or the lipid comprises an obtusilic acid, caproleic acid, lauroleic acid, linderic acid, myristoleic acid, physeteric acid, tsuzuic acid, palmitoleic acid, petroselinic acid or oleic acid;
or the lipid comprises a polyenoic fatty acid (polyunsaturated fatty acid, or PUFA);
or the lipid comprises an 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;
or the lipid comprises 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;(E) the method of any of (A) to (D), 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; (F) the method of any of (A) to (E), wherein contacting conditions comprise higher water conditions for the selective hydrolysis reaction; (G) the method of any of (A) to (E), wherein contacting conditions comprise reaction conditions comprising a pH in the range of about 4 to about 10; (H) the method of any of (A) to (G), further comprising removing from the oil the hydrolyzed (released) fatty acid; (I) the method of any of (H), wherein the hydrolyzed fatty acid is removed from the oil by steam distillation; (J) the method of any of (A) to (I), wherein the enzyme is added to the oil before, during or after a degumming step, or any combination thereof; (K) the method of any of (A) to (J), wherein the hydrolyzed fatty acid is removed from the oil by a saponification reaction or use of a silica; (L) the method of any of (A) to (K), 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; (M) the method of any of (A) to (L), wherein the provided enzyme specifically hydrolyzes fatty acids having various degrees of saturation; (N) the method of any of (A) to (M), wherein the provided enzyme has mono-, di-, or triglyceride selectivity to fatty acids; (O) the method of any of (A) to (N), wherein the provided enzyme has cis- versus trans-fatty acid specificity; (P) the method of any of (A) to (O), wherein the provided enzyme has conjugated versus unconjugated fatty acid specificity; (Q) the method of any of (A) to (P), wherein the provided enzyme has fatty acid chain length specificity; (R) the method of any of (A) to (O), wherein the provided enzyme specifically hydrolyzes oxidized lipids or non-oxidized lipids; (S) the method of any of (A) to (T), wherein the provided enzyme has regioselective catalytic activity; (T) the method of any of (A) to (S), wherein the regioselective catalytic activity comprises selective Sn-1 versus Sn-2 versus Sn-3 reactivity;
or(U) the method of any of (A) to (T), wherein the provided enzyme has positionally selective catalytic activity. - View Dependent Claims (17)
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2. A method for generating one or more fatty acid species comprising
(A) (a) providing an oil or a lipid comprising at least one species of fatty acid; -
(b) providing an enzyme capable of selectively hydrolyzing (releasing) one or more particular fatty acid species 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 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; (B) the method of (A), wherein the enzyme 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); (C) the method of (A) or (B), wherein the oil comprises a plant oil, an animal oil or a microbial oil, or a plant oil comprising a vegetable oil;
or an 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;(D) the method of (A), (B) or (C), wherein the lipid comprises a glyceride, a glycolipid, a phospholipid, a sphingolipid, a coenzyme A, an oxidized lipid or an ether lipid, or the lipid comprises a linoleic acid (cis-9, cis-12-octadecadienoic acid), linolenic acid, palmitic acid or stearic acid;
or the lipid comprises a saturated fatty acid;
or the lipid comprises 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;
or the lipid comprises a monoenoic fatty acid;
or the lipid comprises an obtusilic acid, caproleic acid, lauroleic acid, linderic acid, myristoleic acid, physeteric acid, tsuzuic acid, palmitoleic acid, petroselinic acid or oleic acid;
or the lipid comprises a polyenoic fatty acid (polyunsaturated fatty acid, or PUFA);
or the lipid comprises an 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;
or the lipid comprises 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;
or(E) the method of any of (A) to (D), 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; (F) the method of any of (A) to (E), wherein contacting conditions comprise higher water conditions for the selective hydrolysis reaction; (G) the method of any of (A) to (E), wherein contacting conditions comprise reaction conditions comprising a pH in the range of about 4 to about 10; (H) the method of any of (A) to (G), further comprising removing from the oil the hydrolyzed (released) fatty acid; (I) the method of any of (H), wherein the hydrolyzed fatty acid is removed from the oil by steam distillation; (J) the method of any of (A) to (I), wherein the enzyme is added to the oil before, during or after a degumming step, or any combination thereof; (K) the method of any of (A) to (J), wherein the hydrolyzed fatty acid is removed from the oil by a saponification reaction or use of a silica; (L) the method of any of (A) to (K), 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; (M) the method of any of (A) to (L), wherein the provided enzyme specifically hydrolyzes fatty acids having various degrees of saturation; (N) the method of any of (A) to (M), wherein the provided enzyme has mono-, di-, or triglyceride selectivity to fatty acids; (O) the method of any of (A) to (N), wherein the provided enzyme has cis- versus trans-fatty acid specificity; (P) the method of any of (A) to (O), wherein the provided enzyme has conjugated versus unconjugated fatty acid specificity; (Q) the method of any of (A) to (P), wherein the provided enzyme has fatty acid chain length specificity; (R) the method of any of (A) to (Q), wherein the provided enzyme specifically hydrolyzes oxidized lipids or non-oxidized lipids; (S) the method of any of (A) to (T), wherein the provided enzyme has regioselective catalytic activity; (T) the method of any of (A) to (S), wherein the regioselective catalytic activity comprises selective Sn-1 versus Sn-2 versus Sn-3 reactivity;
or(U) the method of any of (A) to (T), wherein the provided enzyme has positionally selective catalytic activity.
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3-16. -16. (canceled)
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18-36. -36. (canceled)
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37. A method for making a confectionary fat low in a particular fatty acid species comprising
(a) providing a confectionary fat comprising an oil or a lipid comprising at least one species of fatty acid; -
(b) providing an enzyme capable of selectively hydrolyzing (releasing) the fatty acid species of (a) from the oil or lipid; (c) contacting the confectionary fat of (a) with the enzyme of (b) under conditions wherein the enzyme selectively hydrolyzes at least one fatty acid species molecule, thereby making a confectionary fat having at least one fewer fatty acid species molecule.
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38. A method for making a synthetic lubricant or fuel fat low in a particular fatty acid species comprising
(A) (a) providing a synthetic lubricant comprising an oil or a lipid comprising at least one species of fatty acid; -
(b) providing an enzyme capable of selectively hydrolyzing (releasing) the fatty acid species of (a) from the oil or lipid; (c) contacting the synthetic lubricant of (a) with the enzyme of (b) under conditions wherein the enzyme selectively hydrolyzes at least one fatty acid species molecule, thereby making a synthetic lubricant having at least one fewer fatty acid species molecule;
or(B) the method of (A), wherein the provided enzyme specifically hydrolyzes unsaturated fatty acids, thereby generating a stable lubricant.
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39. (canceled)
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40. A method for making a paint or coating low in a particular fatty acid species comprising
(a) providing a paint or coating comprising an oil or a lipid comprising at least one species of fatty acid; -
(b) providing an enzyme capable of selectively hydrolyzing (releasing) the fatty acid species of (a) from the oil or lipid; and (c) contacting the paint or coating of (a) with the enzyme of (b) under conditions wherein the enzyme selectively hydrolyzes at least one fatty acid species molecule, thereby making a paint or coating having at least one fewer fatty acid species molecule.
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41. A method for making a synthetic fuel comprising an oil or a lipid comprising a particular fatty acid species comprising
(a) providing a synthetic fuel comprising an oil or a lipid comprising at least one species of fatty acid; -
(b) providing an enzyme capable of selectively hydrolyzing (releasing) the fatty acid species of (a) from the oil or lipid; and (c) contacting the synthetic fuel of (a) with the enzyme of (b) under conditions wherein the enzyme selectively hydrolyzes at least one fatty acid species molecule, thereby making a synthetic fuel having at least one fewer fatty acid species molecule.
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42. A method for making an oil or a lipid comprising a particular fatty acid species comprising
(a) providing an oil or a lipid and a particular fatty acid species; -
(b) providing an enzyme capable of selectively adding (esterifying) the fatty acid species of (a) to the oil or lipid; and (c) contacting the oil or lipid of (a) with the enzyme of (b) under conditions wherein the enzyme selectively adds (esterifies) at least one fatty acid species molecule, thereby making an oil or a lipid having at least one additional fatty acid species molecule.
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43. A method for making an oil or a lipid low comprising a particular fatty acid species comprising
(a) providing a glycerol and a particular fatty acid species; -
(b) providing an enzyme capable of selectively adding (esterifying) the fatty acid species of (a) to the glycerol; and (c) contacting the glycerol with the enzyme of (b) under conditions wherein the enzyme selectively adds (esterifies) at least one fatty acid species molecule, thereby making an oil or a lipid having at least one additional fatty acid species molecule.
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44. A method for making a composition comprising a particular fatty acid species comprising
(A) (a) providing a composition and a particular fatty acid species; -
(b) providing an enzyme capable of selectively adding (esterifying) the fatty acid species of (a) to the composition; and (c) contacting the composition with the enzyme of (b) under conditions wherein the enzyme selectively adds (esterifies) at least one fatty acid species molecule to the composition, thereby making a composition having at least one or an additional fatty acid species molecule; (B) the method of (A), wherein the composition comprises an oil, or the oil comprises a plant oil, an animal oil or a microbial oil, or the oil comprises a plant oil comprising a vegetable oil;
or 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;(C) the method of (A) or (B), wherein the composition comprises a glyceride, a glycolipid, a phospholipid, a sphingolipid, a coenzyme A, an oxidized lipid or an ether lipid;
or(D) the method of (A) or (B), wherein the composition comprises a small molecule, a protein or a carbohydrate.
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45-50. -50. (canceled)
Specification