US 12,435,349 B2 · Enzymatic method for the production of l-glufosinate p-alkyl esters

Abstract

An enzymatic method for the production of an L-glufosinate P-alkyl ester can be performed. This method is characterized by reacting an L-glufosinate P-alkyl ester carbamoylate to give the corresponding L-glufosinate P-alkyl ester. This is catalyzed by a carbamoylase. The L-glufosinate P-alkyl ester carbamoylate employed may be obtained by a reaction from the corresponding L-glufosinate hydantoin P-alkyl ester. This is catalyzed by a hydantoinase, preferably an L-enantioselective hydantoinase. In a second aspect, an enzymatic method for enantioselective production of an L-glufosinate P-alkyl ester from a mixture MIIIA of L- and D-glufosinate P-alkyl ester hydantoins can be performed. The L-glufosinate P-alkyl ester obtained in the methods according to the first or second aspect of the invention may be saponified to give L-glufosinate.

Claims19

Dependent claims

A method for the production of an L-glufosinate P-alkyl ester according to formula L-(I), the method comprising:

reacting a compound according to formula L-(II) to give a compound according to formula L-(I):
wherein the reacting comprises hydrolyzing L-(II) to give L-(I);
wherein the hydrolyzing of L-(II) to give L-(1) is catalyzed by an L-carbamoylase,
wherein R is an alkyl group or an aryl group;
and
wherein the polypeptide sequence of the L-carbamoylase is selected from the group consisting of SEQ ID NO:
1 and variants thereof, SEQ ID NO:
2 and variants thereof, SEQ ID NO:
3 and variants thereof, SEQ ID NO:
4 and variants thereof, SEQ ID NO:
5 and variants thereof, SEQ ID NO:
6 and variants thereof, SEQ ID NO:
7 and variants thereof, SEQ ID NO:
8 and variants thereof, and SEQ ID NO:9 and variants thereof,
wherein the variants have at least 90% sequence identity to the referenced polypeptide sequence.

12 more elements

A method for the production of an L-glufosinate P-alkyl ester according to formula L-(I), wherein R is an alkyl group or aryl group:

the method comprising:
(i-A) providing a mixture MIA comprising both enantiomers L-(III) and D-(III),
wherein R has the same meaning as described for L-(I):
(i-B) optionally reacting at least a part of the compounds D-(III) comprised by the mixture MIA into L-(III), giving a composition Mus comprising L-(III) and optionally its enantiomer D-(III);
(ii) subjecting mixture MINIA or, in case (i-B) is carried out, composition Mma, to a reaction where a compound according to formula L-(III) is reacted to give a compound according to formula L-(II), giving a composition Mu comprising L-(II) and optionally its enantiomer D-(II), wherein L-(II) and D-(II) have the following formulae and wherein R in formulae L-(II) and D-(II) has the same meaning as described for L-(I):
(iii) subjecting Mn to a reaction where a compound according to formula L-(II) is reacted to give a compound according to formula L-(I), giving a composition Ma comprising L-(I) and optionally its enantiomer D-(I), wherein, in case Mi comprises both enantiomers L-(I) and D-(I), a molar ratio of L-(I) to D-(I) in Mr is greater than a molar ratio of L-(III) to D-(III) in MIA, wherein D-(I) has the following formula and wherein R in formula D-(I) has the same meaning as described for L-(I):
wherein the reacting of L-(II) to give L-(1) is catalyzed by an L-carbamoylase
wherein the polypeptide sequence of the L-carbamoylase is selected from the group consisting of SEQ ID NO:
1 and variants thereof, SEQ ID NO:
2 and variants thereof, SEQ ID NO:
3 and variants thereof, SEQ ID NO:
4 and variants thereof, SEQ ID NO:
5 and variants thereof, SEQ ID NO:
6 and variants thereof, SEQ ID NO:
7 and variants thereof, SEQ ID NO:
8 and variants thereof, and SEQ ID NO:
9 and variants thereof
wherein the variants have at least 90% sequence identity to the referenced polypeptide sequence.

15 more elements

Dependencies are inferred from the claim text.

Enzymatic method for the production of l-glufosinate p-alkyl esters

Life of this patent

Enzymatic method for the production of l-glufosinate p-alkyl esters

Life of this patent

Abstract

Claims19