Enzymatic synthesis of acetoacetate esters and derivatives

• US 8,105,809 B2
• Filed: 07/03/2008
• Issued: 01/31/2012
• Est. Priority Date: 07/03/2008
• Status: Active Grant

• Current Assignee: Cerecin, Inc.
• Original Assignee: Accela Incorporated (Piksel Incorporated)
• Inventors: Henderson, Samuel T.
• Primary Examiner(s): Kim, Taeyoon
• Application Number:
  US12/167,840
• Publication Number:
  US 20100003730A1
• Time in Patent Office: 1,307 Days
• Field of Search: 435/135, 560/178
• US Class Current: 435/135
• CPC Class Codes: C12P 7/62 Carboxylic acid esters
• CPC Class Codes: C12P 7/6458 by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis

Abstract

In one embodiment, the present invention includes a method for the synthesis of an ester derivative of acetoacetate. The method includes providing a first ester of acetoacetate and providing an alcohol. The method further includes combining the first ester of acetoacetate and the alcohol in the presence of an enzyme capable of transesterification in a non-aqueous solvent to form the ester derivative of acetoacetate. The method results in the formation of the ester derivative of acetoacetate, which, in one embodiment, is monoacetoacetin.

Claims

1. A method for the synthesis of an ester derivative of acetoacetate, comprising providing a first ester of acetoacetate having of formula I:

2. The method of claim 1, wherein the compound is glycerol and the ester derivative of acetoacetate is monoglyceride of acetoacetate.

3. The method of claim 1, wherein the compound is glucose and the first ester of acetoacetate is glucose acetyl acetate ester.

4. The method of claim 1, wherein the non-aqueous solvent is acetonitrile.

5. The method of claim 1, further comprising purification of the ester derivative of acetoacetate.