Dehydration and amination of alpha-, beta-dihydroxy carbonyl compounds to alpha-amino acids

Patent metadata

Field	Value
Publication number	US-11414376-B2
Application number	US-201917046730-A
Country	US
Kind code	B2
Filing date	Apr 2, 2019
Priority date	Apr 13, 2018
Publication date	Aug 16, 2022
Grant date	Aug 16, 2022

Abstract

Processes are disclosed for the synthesis of an α-amino acid or α-amino acid derivative, from a starting compound or substrate having a carbonyl functional group (C═O), with hydroxy-substituted carbon atoms at alpha (α) and beta (β) positions, relative to the carbonyl functional group. According a particular embodiment, an α-, β-dihydroxy carboxylic acid or carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the α-hydroxy group to a second carbonyl group (adjacent a carbonyl group of the starting compound) and removal of the β-hydroxy group. The dicarbonyl intermediate is optionally cracked to form a second, in this case cracked, dicarbonyl intermediate having fewer carbon atoms relative to the dicarbonyl intermediate but preserving the first and second carbonyl groups. Either or both of the dicarbonyl intermediate and the cracked dicarbonyl intermediate may be aminated to convert the second carbonyl group to an amino (—NH2) group, for producing the corresponding α-amino acid(s).

First claim

The invention claimed is:

1. A method for synthesizing an α-amino acid or α-amino acid derivative, the method comprising:
reacting an α-, β-dihydroxy carboxylate starting compound in a reaction mixture under hydrogen pressure and comprising an aminating agent and a cracking catalyst, to form the α-amino acid or α-amino acid derivative,
wherein the α-amino acid or α-amino acid derivative has fewer carbon atoms, relative to the starting compound.

2. The method of claim 1 , wherein the reaction mixture is under a hydrogen partial pressure of at least about 3 MPa (435 psi).

3. The method of claim 1 , wherein the aminating agent is gaseous or aqueous ammonia, or an ammonium salt.

4. The method of claim 1 , wherein the cracking catalyst comprises tungsten, molybdenum, or vanadium.

5. The method of claim 1 , wherein the reaction mixture further comprises a hydrogenation catalyst.

6. The method of claim 5 , wherein the hydrogenation catalyst comprises ruthenium and a solid support.

7. A method for synthesizing homoserine, the method comprising:
reacting erythronic acid in a reaction mixture under hydrogen pressure and comprising an aminating agent, to form homoserine.

8. The method of claim 7 , further comprising reacting the homoserine with a mercaptan compound to produce methionine.

9. The method of claim 7 , wherein the erythronic acid is dehydrated to produce a corresponding dicarbonyl intermediate, with a portion of the dicarbonyl intermediate being reductively aminated to produce homoserine and further comprising cracking another portion of the dicarbonyl intermediate to form pyruvic acid and reductively aminating the pyruvic acid to produce alanine.

Assignees

• Archer Daniels Midland Co

Inventors

• Brazdil James
• Rogness Donald
• Ma chi-cheng

Classifications

• C07C227/08 Primary

  by reaction of ammonia or amines with acids containing functional groups · CPC title

• C07C51/353

  by isomerisation; by change of size of the carbon skeleton · CPC title

• B01J23/6527

  Tungsten · CPC title

• C07C51/02

  from salts of carboxylic acids · CPC title

• B01J21/18

  Carbon · CPC title