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    METHODS FOR IMPROVING YIELDS OF L-GLUFOSINATE
    11.
    发明申请
    METHODS FOR IMPROVING YIELDS OF L-GLUFOSINATE 有权

    公开(公告)号：US20210214754A1

    公开(公告)日：2021-07-15

    申请号：US17272803

    申请日：2019-09-04

    Applicant: BASF SE

    Inventor： Brian Michael Green ,  Danielle Marie Estridge

    IPC: C12P7/52

    Abstract: Compositions and methods for the production of L-glufosinate are provided. The method involves converting racemic glufosinate to the L-glufosinate enantiomer or converting PPO to L-glufosinate in an efficient manner. In particular, the method involves the specific amination of PPO to L-glufosinate, using L-glutamate, racemic glutamate, or another amine source as an amine donor. PPO can be obtained by the oxidative deamination of D-glufosinate to PRO (2-oxo-4-(hydroxy(methyl)phosphinoyl)butyric acid) or generated via chemical synthesis. PPO is then converted to L-glufosinate using a transaminase in the presence of an amine donor. When the amine donor donates an amine to PPO, L-glufosinate and a reaction by product are formed. Because the PPO remaining represents a yield loss of L-glufosinate, it is desirable to minimize the amount of PPO remaining in the reaction mixture. Degradation, other chemical modification, extraction, sequestration, binding, or other methods to reduce the effective concentration of the by-product, i.e., the corresponding alpha ketoacid or ketone to the chosen amine donor will shift the reaction equilibrium toward L-glufosinate, thereby reducing the amount of PPO and increasing the yield of L-glufosinate. Therefore, the methods described herein involve the conversion or elimination of the alpha ketoacid or ketone by-product to another product to shift the equilibrium towards L-glufosinate.

    METHODS FOR THE PURIFICATION OF L-GLUFOSINATE
    12.
    发明公开
    METHODS FOR THE PURIFICATION OF L-GLUFOSINATE 审中-公开

    公开(公告)号：US20240270770A1

    公开(公告)日：2024-08-15

    申请号：US18628186

    申请日：2024-04-05

    Applicant: BASF SE

    Inventor： Stephen Craig Fields ,  Matthew Richard Oberholzer ,  Brian Michael Green ,  Samir Kulkarni ,  Jennifer Nelson ,  Patricia Andres

    IPC: C07F9/535 ,  C07F9/30

    CPC classification number: C07F9/535 ,  C07F9/301

    Abstract: Compositions and methods for isolating L-glufosinate from a composition comprising L-glufosinate and glutamate are provided. The method comprises converting the glutamate to pyroglutamate followed by the isolation of L-glufosinate from the pyroglutamate and other components of the composition to obtain substantially purified L-glufosinate. The composition comprising L-glufosinate and glutamate is subjected to an elevated temperature for a sufficient time to allow for the conversion of glutamate to pyroglutamate, followed by the isolation of L-glufosinate from the pyroglutamate and other components of the composition to obtain substantially purified L-glufosinate. The glutamate alternatively may be converted to pyroglutamate by enzymatic conversion. The purified L-glufosinate is present in a final composition at a concentration of 90% or greater of the sum of L-glufosinate, glutamate, and pyroglutamate. In some embodiments, a portion of the glutamate in the starting composition may be separated from the L-glufosinate using a crystallization step. Solid forms of L-glufosinate materials, including crystalline L-glufosinate ammonium, are also described.

    METHODS FOR THE PURIFICATION OF L-GLUFOSINATE
    15.
    发明公开
    METHODS FOR THE PURIFICATION OF L-GLUFOSINATE 审中-公开

    公开(公告)号：US20230331749A1

    公开(公告)日：2023-10-19

    申请号：US18180701

    申请日：2023-03-08

    Applicant: BASF SE

    Inventor： Stephen Craig Fields ,  Matthew Richard Oberholzer ,  Brian Michael Green ,  Samir Kulkarni ,  Jennifer Nelson ,  Patricia Andres

    IPC: C07F9/535 ,  C07F9/30

    CPC classification number: C07F9/535 ,  C07F9/301

    Abstract: Compositions and methods for isolating L-glufosinate from a composition comprising L-glufosinate and glutamate are provided. The method comprises converting the glutamate to pyroglutamate followed by the isolation of L-glufosinate from the pyroglutamate and other components of the composition to obtain substantially purified L-glufosinate. The composition comprising L-glufosinate and glutamate is subjected to an elevated temperature for a sufficient time to allow for the conversion of glutamate to pyroglutamate, followed by the isolation of L-glufosinate from the pyroglutamate and other components of the composition to obtain substantially purified L-glufosinate. The glutamate alternatively may be converted to pyroglutamate by enzymatic conversion. The purified L-glufosinate is present in a final composition at a concentration of 90% or greater of the sum of L-glufosinate, glutamate, and pyroglutamate. In some embodiments, a portion of the glutamate in the starting composition may be separated from the L-glufosinate using a crystallization step. Solid forms of L-glufosinate materials, including crystalline L-glufosinate ammonium, are also described.

    METHODS FOR MAKING L-GLUFOSINATE
    17.
    发明申请
    METHODS FOR MAKING L-GLUFOSINATE 有权

    公开(公告)号：US20210395790A1

    公开(公告)日：2021-12-23

    申请号：US17464887

    申请日：2021-09-02

    Applicant: BASF SE

    Inventor： Brian Michael Green ,  Michelle Lorraine Gradley

    IPC: C12P13/02 ,  C12P41/00 ,  C12P9/00 ,  C12P13/04 ,  A01N25/30 ,  A01N57/20 ,  C12N1/20 ,  C12N9/10

    Abstract: Methods for the production of L-glufosinate (also known as phosphinothricin or (S)-2-amino-4-(hydroxy(methyl)phosphonoyl)butanoic acid) are provided. The methods comprise a two-step process. The first step involves the oxidative deamination of D-glufosinate to PPO (2-oxo-4-(hydroxy(methyl)phosphinoyl)butyric acid). The second step involves the specific amination of PPO to L-glufosinate, using an amine group from one or more amine donors. By combining these two reactions, the proportion of L-glufosinate in a mixture of L-glufosinate and D-glufosinate can be substantially increased.

    Methods for the purification of L-glufosinate
    20.
    发明授权
    Methods for the purification of L-glufosinate 有权

    公开(公告)号：US11634442B2

    公开(公告)日：2023-04-25

    申请号：US16631963

    申请日：2018-07-17

    Applicant: BASF SE

    Inventor： Stephen Craig Fields ,  Matthew Richard Oberholzer ,  Brian Michael Green ,  Samir Kulkarni ,  Jennifer Nelson ,  Patricia Andres

    IPC: C07F9/535 ,  C07F9/30

    Abstract: Compositions and methods for isolating L-glufosinate from a composition comprising L-glufosinate and glutamate are provided. The method comprises converting the glutamate to pyroglutamate followed by the isolation of L-glufosinate from the pyroglutamate and other components of the composition to obtain substantially purified L-glufosinate. The composition comprising L-glufosinate and glutamate is subjected to an elevated temperature for a sufficient time to allow for the conversion of glutamate to pyroglutamate, followed by the isolation of L-glufosinate from the pyroglutamate and other components of the composition to obtain substantially purified L-glufosinate. The glutamate alternatively may be converted to pyroglutamate by enzymatic conversion. The purified L-glufosinate is present in a final composition at a concentration of 90% or greater of the sum of L-glufosinate, glutamate, and pyroglutamate. In some embodiments, a portion of the glutamate in the starting composition may be separated from the L-glufosinate using a crystallization step. Solid forms of L-glufosinate materials, including crystalline L-glufosinate ammonium, are also described.

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