IP Library › Granted Patent US 12,398,410
Granted Patent B2
US 12,398,410 · App. 18/846,061 · Granted Aug 26, 2025

Enzymatic method for the production of L-glufosinate P-esters

Inventors: Ludger Lautenschütz (Hanau, DE); Steffen Oßwald (Nidderau, DE); Markus Pötter (Muenster, DE); Jakob Müller (Haltern am See, DE)
Assignee: Evonik Operations GmbH
C12P13/04C12N9/80C12N9/86C12N9/90C12N15/52C12N15/70C12Y305/01087C12Y305/02002C12Y501/99005
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Quick Facts
Patent No.
US 12,398,410
App. No.
18/846,061
Granted
Aug 26, 2025
Kind
B2
Abstract

A first enzymatic method for the production of an L-glufosinate P-ester includes reacting an L-glufosinate P-ester carbamoylate to give the corresponding L-glufosinate P-ester in the presence of a carbamoylase as a catalyzer. A second enzymatic method includes the enantioselective production of an L-glufosinate P-ester from a mixture M IIIA of L- and D-glufosinate P-ester hydantoins. The L-glufosinate P-ester obtained in the two methods may be saponified to give L-glufosinate.

Claims (31)

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

(c) reacting a compound according to formula L-(II) to give a compound according to formula L-(I)

wherein the reaction according to (c) is catalyzed by an L-carbamoylase E 1 categorized in EC class 3.5.1.87,

wherein R 1L and R 2L are radicals selected from the group consisting of formulae (VIII), (IX), and (X)

 and

wherein R 1L =R 2L .

2. The method according to claim 1 , wherein R 1L and R 2L are radicals that are each independently selected from the group consisting of formulae (IX) and (X).

3. The method according to claim 1 , wherein a polypeptide sequence of the L-carbamoylase E 1 is selected from the group consisting of SEQ ID NO: 1, SEQ ID NO: 2, SEQ ID NO: 3 SEQ ID NO: 4 SEQ ID NO: 5, SEQ ID NO: 6, SEQ ID NO: 7, SEQ ID NO: 8, SEQ ID NO: 9, and variant amino acid sequences having at least 90% sequence identity to one of SEQ ID NOS: 1-9.

4. The method according to claim 1 , wherein the compound according to formula L-(II) is obtained by (b) in which a compound according to formula L-(III) is reacted to give a compound according to formula L-(II):

wherein the reaction according to (b) is catalyzed by a hydantoinase E 2 categorized in EC class 3.5.2.2, and

wherein R 3L is a radical that is selected from the group consisting of formulae (VIII), (IX), and (X).

5. The method according to claim 4 , wherein R 3L is a radical of the formula (VIII).

6. The method according to claim 4 , wherein a polypeptide sequence of the hydantoinase E 2 is selected from the group consisting of SEQ ID NO: 10, SEQ ID NO: 11, SEQ ID NO: 12, SEQ ID NO: 13, SEQ ID NO: 14, SEQ ID NO: 16, and variant amino acid sequences having at least 90% sequence identity to one of SEQ ID NOS: 10-16.

7. The method according to claim 4 , wherein the hydantoinase E 2 is an L-hydantoinase E 2 .

8. The method according to claim 4 , wherein the compound according to formula L-(III) is obtained by (a) in which a compound according to formula D-(III) is reacted to give a compound according to formula L-(III):

 and

wherein R 3D is a radical that is selected from the group consisting of formulae (VIII), (IX), and (X).

9. The method according to claim 8 , wherein R 3D is a radical of the formula (VIII).

10. The method according to claim 8 , wherein the reaction according to (a) is catalyzed by a hydantoin racemase E 3 categorized in EC class 5.1.99.5.

11. The method according to claim 10 , wherein a polypeptide sequence of the hydantoin racemase E 3 is selected from the group consisting of SEQ ID NO: 17, SEQ ID NO: 18, SEQ ID NO: 19, SEQ ID NO: 20, SEQ ID NO: 21, SEQ ID NO: 22, SEQ ID NO: 23, SEQ ID NO: 24, SEQ ID NO: 25, SEQ ID NO: 26, and variant amino acid sequences having at least 90% sequence identity to one of SEQ ID NOS: 18-26.

12. The method according to claim 1 , wherein the compound according to formula L-(I) is saponified to give L-glufosinate.

13. A method for the production of an L-glufosinate P-ester according to formula L-(I):

the method comprising:

(i-A) providing a mixture MIIA comprising at least one compound L-(III) and at least one compound D-(III), wherein L-(III) and D-(III) have the following formulae:

(i-B) (a) reacting at least a part of the compounds according to formula D-(III) comprised by the mixture M IIIA into the compound according to formula L-(III) to form a composition M IIIB comprising compounds according to formula L-(III) and compounds according to formula D-(III), and

(ii) subjecting composition M IIIB to a reaction according to (b), giving a composition Mu comprising at least one compound according to formula L-(II) and at least one compound according to formula D-(II), wherein the reaction according to (b) is catalyzed by a hydantoinase E 2 categorized in EC class 3.5.2.2, wherein L-(II) and D-(II) have the following formulae:

 and

(iii) subjecting composition Mu to a reaction according to (c), wherein the reaction according to (c) is catalyzed by an L-carbamoylase E 1 , giving a composition M I comprising at least one compound according to formula L-(I) and at least one compound according to formula D-(I),

wherein a molar ratio of all compounds according to formula L-(I) in composition M 1 to all compounds according to formula D-(I) in composition M I is greater than a molar ratio of all compounds according to formula L-(III) in M IIIA to all compounds of formula D-(III) in M IIIA , wherein D-(I) has the following formula:

 and

wherein R 1L , R 1D , R 2L , R 2D , R 3L and R 3D are each the same radical selected from the group consisting of formulae (VIII), (IX), and (X) having the following formulae:

Continuity (1)
Related Publication 20250109417A1 · Apr 3, 2025
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