Process for the preparation of (S)-2-amino-non-8-enoic acid

Patent metadata

Field	Value
Publication number	US-10465216-B2
Application number	US-201816113738-A
Country	US
Kind code	B2
Filing date	Aug 27, 2018
Priority date	Oct 3, 2014
Publication date	Nov 5, 2019
Grant date	Nov 5, 2019

Abstract

Disclosed herein is a process for preparing enantioenriched (S)-2-aminonon-8-enoic acid by amination of 2-oxonon-8-enoic acid in the presence of an enzyme and an ammonia source.

First claim

We claim:

1. A method for preparing a compound of formula (IV):

wherein R 1 is lower alkyl;
comprising reacting a reagent of formula (II) with a compound of formula (III),

wherein independently for each occurrence
R 1 is lower alkyl; and M is selected from Li, MgCl, MgBr, and MgI.

2. The method of claim 1 , wherein R 1 is ethyl.

3. The method of claim 1 , wherein M is MgBr.

4. The method of claim 1 , wherein R 1 is ethyl; and M is MgBr.

5. The method of claim 1 , further comprising hydrolyzing the compound of formula (IV) to produce 2-oxonon-8-enoic acid.

6. The method of claim 2 , further comprising aminating the 2-oxonon-8-enoic acid in the presence of an enzyme and an ammonia source to produce enantioenriched 2-aminonon-8-enoic acid;
wherein
the enzyme is a leucine dehydrogenase (LeuDH) from Bacillus cereus;
the ammonia source comprises an ammonium chloride or ammonium hydroxide buffer solution; and
the LeuDH is a wild type LeuDH or a mutant LeuDH having a mutation at position 42 of the LeuDH amino acid sequence.

Assignees

• Abbvie Inc

Inventors

• Abrahamson Michael J
• Pruyne Julie J
• Kielbus Angelica B
• Lallaman John E
• Reddy Rajarathnam E
• Chemburkar Sanjay R

Classifications

• C12Y104/01009

  Leucine dehydrogenase (1.4.1.9) · CPC title

• C12P13/04 Primary

  Alpha- or beta- amino acids {(other amino acids C12P13/005)} · CPC title