Enantioselective oligomerization of α-hydroxy carboxylic acids and α-amino acids

• US 6,939,693 B2
• Filed: 05/02/2002
• Issued: 09/06/2005
• Est. Priority Date: 10/29/1999
• Status: Expired due to Fees

• Current Assignee: Novus International, Inc. (Nippon Soda Company Limited)
• Original Assignee: Novus International, Inc. (Nippon Soda Company Limited)
• Inventors: Schasteen, Charles S., Nam, Paul K. S., Rajesh, Mathur P., Kapila, Shubhender, Lorbert, Stephen J., Forciniti, Daniel
• Primary Examiner(s): Lilling, Herbert J.
• Application Number:
  US10/136,974
• Publication Number:
  US 20030143661A1
• Time in Patent Office: 1,223 Days
• Field of Search: 435/106, 435/280, 528/361
• US Class Current: 435/106
• CPC Class Codes: A23K 20/105 Aliphatic or alicyclic compounds
• CPC Class Codes: A23K 20/142 Amino acids; Derivatives thereof
• CPC Class Codes: A23K 20/147 Polymeric derivatives, e.g. peptides or proteins
• CPC Class Codes: A23K 20/189 Enzymes
• CPC Class Codes: A23K 50/00 Feeding-stuffs specially adapted for particular animals
• CPC Class Codes: A23K 50/10 for ruminants
• CPC Class Codes: A23K 50/80 for aquatic animals, e.g. fish, crustaceans or molluscs
• CPC Class Codes: C07K 2/00 Peptides of undefined number of amino acids; Derivatives thereof
• CPC Class Codes: C07K 7/06 having 5 to 11 amino acids
• CPC Class Codes: C12P 21/00 Preparation of peptides or proteins single cell protein C12N1/00

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.

Claims

1. A process for the preparation of an oligomer, the process comprising:

forming a reaction mixture comprising an enzyme, an enantiomeric mixture of an α

-amino acid or a derivative thereof, and an enantiomeric mixture of an α

-hydroxy carboxylic acid or a derivative thereof, wherein the α

-hydroxy carboxylic acid comprises 2-hydroxy-4-(methylthio)butyric 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.

wherein the formed oligomer comprises an oligomer of two or more α

-amino acid monomers bonded to a residue of the α

-hydroxy carboxylic acid or a derivative thereof by an amide or ester linkage.