Enantioselective oligomerization of alpha-hydroxy carboxylic acids and alpha-amino acids
First Claim
1. A process for the preparation of an oligomer, the process comprising:
- forming a reaction mixture comprising an enzyme, and an enantiomeric mixture of an α
-amino acid or a derivative thereof; and
forming an oligomer from the reaction mixture, said oligomer incorporating one of the members of the enantiomeric mixture of the α
-amino acid or derivative thereof in preference to the other member.
1 Assignment
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Accused Products
Abstract
An enzymatic synthesis and composition of oligomers and co-oligomers comprised of α-hydroxy carboxylic acids and α-amino acids or peptides is disclosed. In a preferred embodiment, a α-hydroxy carboxylic acid with a specific chiral configuration is linked by an amide linkage to a α-amino acid specific with a specific chiral configuration or linked by an amide linkage to a peptide made up of α-amino acid monomers having identical chiral configurations. Proteolytic enzymes catalyze oligomerization of the α-hydroxy carboxylic acid and α-amino acid. The degree and distribution of oligomerization varies upon the type and concentrations of different reaction mixtures utilized and upon the length of allowed reaction time. The resultant oligomers may be provided to animals such as ruminants as bioavailable amino acid supplements that are resistant to degradation in the rumen and other animals such as swine, poultry and aquatic animals.
24 Citations
85 Claims
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1. A process for the preparation of an oligomer, the process comprising:
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forming a reaction mixture comprising an enzyme, and an enantiomeric mixture of an α
-amino acid or a derivative thereof; and
forming an oligomer from the reaction mixture, said oligomer incorporating one of the members of the enantiomeric mixture of the α
-amino acid or derivative thereof in preference to the other member. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17)
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18. A composition comprising a residue of an α
- -hydroxy carboxylic acid bonded to a peptide by an amide linkage, said peptide comprising two or more α
-amino acid residues, each of said α
-amino acids being independently selected from the group consisting of α
-amino acids. - View Dependent Claims (19, 20)
- -hydroxy carboxylic acid bonded to a peptide by an amide linkage, said peptide comprising two or more α
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21. A composition comprising a residue of an α
- -hydroxy carboxylic acid bonded to a peptide by an ester linkage, said peptide comprising two or more α
-amino acid residues, each of said α
-amino acids being independently selected from the group consisting of α
-amino acids. - View Dependent Claims (22, 23)
- -hydroxy carboxylic acid bonded to a peptide by an ester linkage, said peptide comprising two or more α
- 24. A composition comprising:
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40. A process for providing a food ration to an animal, the process comprising:
- providing an oligomer or co-oligomer composition prepared from a mixture containing an enzyme, an α
-amino acid or a derivative thereof, and optionally, an α
-hydroxy carboxylic acid or a derivative thereof,wherein the method of administration is selected from the group consisting of oral administration, eye spray, placement in ear, placement in nasal cavity, bucchal administration, sublingual administration, rectal administration and injection. - View Dependent Claims (41, 42, 43, 44, 45, 46, 47)
- providing an oligomer or co-oligomer composition prepared from a mixture containing an enzyme, an α
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48. An orally administered dietary supplement comprising a vitamin, a mineral or a nutrient coated with an oligomeric coating, said coating comprising a residue of an α
- -hydroxy carboxylic acid bonded to a peptide by an amide linkage, said peptide comprising two or more α
-amino acid residues, each of said α
-amino acids being independently selected from the group consisting of α
-amino acids.
- -hydroxy carboxylic acid bonded to a peptide by an amide linkage, said peptide comprising two or more α
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49. A process for providing an animal with a dietary supplement comprising a vitamin, mineral or nutrient, the process comprising:
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coating said vitamin, mineral or nutrient with a composition to form a dietary supplement, said composition comprising a residue of an α
-hydroxy carboxylic acid bonded to a peptide by an amide linkage, said peptide comprising two or more α
-amino acid residues, each of said α
-amino acids being independently selected from the group consisting of α
-amino acids; and
orally administering the dietary supplement to the animal. - View Dependent Claims (50, 51, 52, 53, 54, 55, 56, 57)
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58. A process for providing an animal with a dietary supplement comprising a vitamin, mineral or nutrient, the process comprising:
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preparing a mixture comprising an enzyme and at least one α
-amino acid, each α
-amino acid being present in the mixture as a free acid, acid halide, amide, ester or anhydride independently of the other,forming an α
-amino acid oligomer in the mixture,coating said vitamin, mineral or nutrient with the α
-amino acid oligomer to form an α
-amino acid oligomer coated dietary supplement, andorally administering the dietary supplement to the animal. - View Dependent Claims (59, 60)
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61. A process for purifying an α
- -hydroxy carboxylic acid enantiomer or derivative thereof from an enantiomeric mixture, the process comprising;
forming a reaction mixture comprising (i) an enantioselective enzyme, (ii) an enantiomeric mixture of an α
-hydroxy carboxylic acid or a derivative thereof, and (iii) an enantiomeric mixture of an α
-amino acid or a derivative thereof;
forming a reaction product from the reaction mixture, the reaction product comprising (i) an oligomer having a first α
-hydroxy carboxylic acid enantiomer of the enantiomeric mixture incorporated therein in preference to the second enantiomer, and (ii) unreacted second enantiomer; and
separating the oligomer and unreacted second enantiomer from the reaction product and each other. - View Dependent Claims (62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73)
- -hydroxy carboxylic acid enantiomer or derivative thereof from an enantiomeric mixture, the process comprising;
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74. A process for purifying an enantiomeric mixture of α
- -amino acid or derivative thereof, the process comprising;
forming a reaction mixture comprising (i) an enzyme, (ii) an enantiomeric mixture of α
-amino acid or a derivative thereof, and (iii) an α
-hydroxy carboxylic acid or a derivative thereof;
forming a reaction product from the reaction mixture, the reaction product comprising (i) an oligomer incorporating a first member of the enantiomeric mixture of α
-amino acid or derivative thereof in preference to a second enantiomer of the enantiomeric mixture or derivative thereof, and (ii) unreacted second enantiomer; and
separating the oligomer and unreacted second enantiomer from the reaction product and each other. - View Dependent Claims (75, 76, 77, 78, 79)
- -amino acid or derivative thereof, the process comprising;
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80. A process for purifying an α
- -amino acid enantiomer or derivative thereof in an enantiomeric mixture, the process comprising;
forming a reaction mixture comprising (i) an enantioselective enzyme and (ii) an enantiomeric mixture of an α
-amino acid or derivative thereof;
forming a peptide reaction product mixture comprising (i) an oligomer or a co-oligomer having a first enantiomer of the enantiomeric mixture incorporated therein in preference to the second enantiomer of the enantiomeric mixture, and (ii) unreacted second enantiomer; and
separating the oligomer or co-oligomer and unreacted second enantiomer from the reaction product mixture and each other - View Dependent Claims (81, 82, 83, 84, 85)
- -amino acid enantiomer or derivative thereof in an enantiomeric mixture, the process comprising;
Specification