Preparation of lipoamino acids and lipopeptides using salts as co-reactants

Patent metadata

Field	Value
Publication number	US-9505706-B2
Application number	US-201514830082-A
Country	US
Kind code	B2
Filing date	Aug 19, 2015
Priority date	Aug 21, 2014
Publication date	Nov 29, 2016
Grant date	Nov 29, 2016

Abstract

Methods for synthesizing a lipoamino acid and a lipopeptide are provided. The method can include reacting a fatty acid with an amino acid or a peptide and a co-reactant salt to form a lipoamino acid or a lipopeptide, respectively. The co-reactant salt is generally a magnesium sulfate, magnesium carbonate, potassium carbonate, iron (II) sulfide (troilite), or a mixture thereof.

First claim

What is claimed:

1. A method of synthesizing a lipoamino acid, the method comprising:
reacting a fatty acid with an amino acid and a co-reactant salt to form a lipoamino acid, wherein the co-reactant salt comprises magnesium sulfate, magnesium carbonate, potassium carbonate, iron (II) sulfide (troilite), or a mixture thereof.

2. The method as in claim 1 , wherein the molar ratio of the amino acid to the fatty acid is about 0.5:1 to about 5:1.

3. The method as in claim 1 , wherein the amino acid comprises alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, other alpha- or of beta- or gamma amino acids or mixtures thereof.

4. The method as in claim 1 , wherein the fatty acid comprises a saturated fatty acid.

5. The method as in claim 4 , wherein the saturated fatty acid comprises caprylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, cetylic acid, heptadecanoic acid, stearic acid, arachidic acid, behenic acid or mixtures thereof or of branched chain saturated fatty acid comprises straight chain fatty acids with one or more alkyl groups bonded to carbons at various locations along the length of the chain.

6. The method as in claim 1 , wherein the fatty acid comprises an unsaturated fatty acid.

7. The method as in claim 6 , wherein the unsaturated fatty acid comprises palmitoleic acid, oleic acid, linoleic acid, conjugated linoleic acid, linolenic acid, γ-linolenic acid, or other unsaturated fatty acids with either or both cis and/or trans configurations at the double bond(s) or mixtures thereof.

8. The method as in claim 1 , wherein the reaction is performed at a reaction temperature of about 30° C. to about 160° C.

9. The method as in claim 1 , wherein the salt consists of an ionic or quasiionic compound or mixture of such compounds.

10. The method as in claim 1 , wherein the cation of the salt consists of monatomic or polyatomic ions and the anion of the salt consists of monatomic or polyatomic ions or mixtures thereof.

11. The method as in claim 1 , wherein the molar ratio of salt to fatty acid is about 0.5:1 to about 2.5:1.

12. The method as in claim 1 , wherein the molar ratio of salt to fatty acid is about 1:1 to about 2:1.

13. The method as in claim 1 , wherein the molar ratio of the amino acid or peptide to the fatty acid is about 0.5:1 to about 5:1.

14. A method of synthesizing a lipopeptide, the method comprising:
reacting a fatty acid with a peptide in the presence of a salt to form a lipopeptide, wherein the co-reactant salt comprises magnesium sulfate, magnesium carbonate, potassium carbonate, iron (II) sulfide (troilite), or a mixture thereof.

15. The method as in claim 14 , wherein the molar ratio of the amino acid or peptide to the fatty acid is about 0.5:1 to about 5:1.

16. The method as in claim 14 , wherein the fatty acid comprises a saturated fatty acid, and wherein the saturated fatty acid comprises caprylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, cetylic acid, heptadecanoic acid, stearic acid, arachidic acid, behenic acid or mixtures thereof or of branched chain saturated fatty acid comprises straight chain fatty acids with one or more alkyl groups bonded to carbons at various locations along the length of the chain.

17. The method as in claim 16 , wherein the fatty acid comprises an unsaturated fatty acid, and wherein the unsaturated fatty acid comprises palmitoleic acid, oleic acid, linoleic acid, conjugated linoleic acid, linolenic acid, γ-linolenic acid, or other unsaturated fatty acids with either or both cis and/or trans configurations at the double bond(s) or mixtures thereof. The method as in claim 1 , wherein the reaction is performed at a reaction temperature of about 30° C. to about 160° C.

18. The method as in claim 14 , wherein the salt consists of an ionic or quasiionic compound or mixture of such compounds.

19. The method as in claim 14 , wherein the cation of the salt consists of monatomic or polyatomic ions and the anion of the salt consists of monatomic or polyatomic ions or mixtures thereof.

20. The method as in claim 14 , wherein the molar ratio of salt to fatty acid is about 0.5:1 to about 2.5:1.

Assignees

• Univ South Carolina

Inventors

• Sproul Gordon

Classifications

• C07B43/06

  of amide groups · CPC title

• C07C231/02 Primary

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title

• C07K1/1077

  by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids · CPC title

• C07K1/00

  General methods for the preparation of peptides {, i.e. processes for the organic chemical preparation of peptides or proteins of any length} · CPC title

• C07C233/36

  having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton · CPC title