Enzymatic method for the production of L-glufosinate P-esters
AssigneeEvonik Operations GmbH
InventorsLudger Lautenschütz, Steffen Oßwald, Markus Pötter, Jakob Müller
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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 MIIIA 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.
Claims13
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 E1 categorized in EC class 3.5.1.87,
- wherein R1L and R2L are radicals selected from the group consisting of formulae (VIII), (IX), and (X)
- and
- wherein R1L=R2L.
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 MIIIA into the compound according to formula L-(III) to form a composition MIIIB comprising compounds according to formula L-(III) and compounds according to formula D-(III), and
- (ii) subjecting composition MIIIB 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 E2 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 E1, giving a composition MI 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 M1 to all compounds according to formula D-(I) in composition MI is greater than a molar ratio of all compounds according to formula L-(III) in MIIIA to all compounds of formula D-(III) in MIIIA, wherein D-(I) has the following formula:
- and
- wherein R1L, R1D, R2L, R2D, R3L and R3D are each the same radical selected from the group consisting of formulae (VIII), (IX), and (X) having the following formulae:
Dependencies are inferred from the claim text.