Back to results
US 11,053,518 B2Granted
Method for the preparation of chiral alpha haloalkanoic acids
AssigneeBayer Aktiengesellschaft
InventorsMarkus Spelberg, Julian Egger
Life of this patent
Estimating the term…
Abstract
What is described herein relates to a method of selectively hydrolyzing an enantiomer of an alpha haloalkanoic acid according to formula I employing a polypeptide having dehalogenase activity comprising an amino acid sequence as set forth in SEQ ID NO. 1 or SEQ ID NO. 4 or a sequence with at least 80% sequence identity to either of said sequences and to the use of said method.
Claims13
A method of selectively hydrolyzing the S-enantiomer of an alpha haloalkanoic acid according to formula I,
- wherein X is bromide or chloride and
- R is an alkyl chain of 1 to 6 carbon atoms, wherein said alkyl chain is straight or branched at carbon atoms γ or δ,
- comprising:
- providing a racemate of the R-enantiomer and the S-enantiomer of said alpha haloalkanoic acid,
- providing a polypeptide having dehalogenase activity comprising the amino acid sequence as set forth in SEQ ID NO. 1,
- reacting the racemate for 1-8 hours, wherein
- the pH is in the range of 9-10 and the temperature is in the range of 15-35° C. for the polypeptide with dehalogenase activity comprising the amino acid sequence as set forth in SEQ ID NO. 1,
- and wherein an enantiomeric excess of the R-enantiomer of the haloalkanoic acid of between 90.0% and 99.9% is reached after 1-8 hours, and wherein the concentration of the racemate of said alpha haloalkanoic acid according to Formula I is between 80 and 200 g/L and the polypeptide with dehalogenase activity is comprised within whole cells.
5 more elements
A method of selectively hydrolyzing the S-enantiomer of an alpha haloalkanoic acid according to formula II,
- wherein
- R is an alkyl chain of 1 to 6 carbon atoms, wherein said alkyl chain is straight or branched at carbon atoms γ or δ, and F is a single fluorine atom,
- said method comprising:
- providing a racemate of the R-enantiomer and the S-enantiomer of said alpha haloalkanoic acid,
- providing a polypeptide having dehalogenase activity comprising the amino acid sequence as set forth in SEQ ID NO. 4,
- reacting the racemate for 1-8 hours, wherein the pH is in the range of 9-10 and the temperature is in the range of 55-65° C. for the polypeptide with dehalogenase activity comprising the amino acid sequence as set forth in SEQ ID NO. 4,
- wherein an enantiomeric excess of the R-enantiomer of the haloalkanoic acid of between 90.0% and 99.9% is reached after 1-8 hours, and
- wherein the concentration of the racemate of said alpha haloalkanoic acid according to Formula II is between 80 and 200 g/L and the polypeptide with dehalogenase activity is comprised within whole cells.
5 more elements
Dependencies are inferred from the claim text.