53369-07-6Relevant academic research and scientific papers
Tuning amino acid dehydrogenases with featured sequences for L-phosphinothricin synthesis by reductive amination
Cheng, Feng,Li, Heng,Li, Qing-Hua,Xie, Dong,Xue, Ya-Ping,Zhang, Kai,Zheng, Yu-Guo
, p. 35 - 43 (2020)
Biosynthesizing unnatural chiral amino acids is challenging due to the limited reductive amination activity of amino acid dehydrogenase (AADH). Here, for the asymmetric synthesis of L-phosphinothricin from 2-oxo-4-[(hydroxy)(methyl)phosphinoyl]butyric acid (PPO), a glutamate dehydrogenase gene (named GluDH3) from Pseudomonas monteilii was selected, cloned and expressed in Escherichia coli (E. coli). To boost its activity, a “two-step”-based computational approach was developed and applied to select the potential beneficial amino acid positions on GluDH3. L-phosphinothricin was synthesized by GluDH-catalyzed asymmetric amination using the D-glucose dehydrogenase from Exiguobacterium sibiricum (EsGDH) for NADPH regeneration. Using lyophilized E. coli cells that co-expressed GluDH3_V375S and EsGDH, up to 89.04 g L?1 PPO loading was completely converted to L-phosphinothricin within 30 min at 35 °C with a space-time yield of up to 4.752 kg·L?1·d?1. The beneficial substitution V375S with increased polar interactions between K90, T193, and substrate PPO exhibited 168.2-fold improved catalytic efficiency (kcat/KM) and 344.8-fold enhanced specific activity. After the introduction of serine residues into other GluDHs at specific positions, forty engineered GluDHs exhibited the catalytic functions of “glufosinate dehydrogenase” towards PPO.
L-GLUFOSINATE INTERMEDIATE AND L-GLUFOSINATE PREPARATION METHOD
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Paragraph 0160-0162, (2022/02/05)
Provided are L-glufosinate intermediate preparation method or L-glufosinate preparation method, the method, for preparing L-glufosinate intermediate or L-glufosinate from an L-homoserine derivative, comprising a step of preparing a compound of Chemical Formula 2 from a compound of Chemical Formula 1.
A Single-Transaminase-Catalyzed Biocatalytic Cascade for Efficient Asymmetric Synthesis of l-Phosphinothricin
Cheng, Feng,Li, Ju-Mou,Zhou, Shi-Peng,Liu, Qi,Jin, Li-Qun,Xue, Ya-Ping,Zheng, Yu-Guo
, p. 345 - 348 (2020/10/02)
A single-transaminase-catalyzed biocatalytic cascade was developed by employing the desired biocatalyst, ATA-117-Rd11, that showed high activity toward 2-oxo-4-[(hydroxy)(methyl)phosphinoyl] butyric acid (PPO) and α-ketoglutarate, and low activity against pyruvate. The cascade successfully promotes a highly asymmetric amination reaction for the synthesis of l-phosphinothricin (l-PPT) with high conversion (>95 %) and>99 % ee. In a scale-up experiment, using 10 kg pre-frozen E. coli cells harboring ATA-117-Rd11 as catalyst, 80 kg PPO was converted to ≈70 kg l-PPT after 24 hours with a high ee value (>99 %).
Preparation method of glufosinate-ammonium
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Paragraph 0052-0053; 0055-0057; 0059-0061; 0063-0065, (2021/08/14)
The invention relates to a preparation method of glufosinate-ammonium (I). The method comprises the step of reacting an enantiomerically pure compound of formula (II) with a compound of formula (III) in the presence of a Lewis acid, wherein Hal is a halogen; PG is hydrogen or an amino protecting group; Z is OX or OY; R1 is a C1-C16 alkyl group, cyclohexyl group, cyclopentyl group or phenyl group, and each group can be substituted by hydrogen, a C1-C6 alkyl group, a C1-C6 alkoxy group or a dialkylamino group; R2 is a C1-C8 alkyl group, a C1-C8 ether group or a phenyl group; X and Y are respectively and independently alkyl, alkenyl or aryl; and chiral carbon atoms are marked with *. According to the method disclosed by the invention, high-purity glufosinate-ammonium can be obtained with high yield.
Development of a biocatalytic cascade for synthesis of 2-oxo-4-(hydroxymethylphosphinyl) butyric acid in one pot
Xu, Jianmiao,Zhang, Kai,Cao, Huiting,Li, Heng,Cheng, Feng,Cao, Chenghao,Xue, Ya-Ping,Zheng, Yu-Guo
, p. 190 - 197 (2020/07/30)
2-Oxo-4-(hydroxymethylphosphinyl) butyric acid (PPO) is an important precursor compound for the broad-spectrum herbicide l-glufosinate (L-PPT). In this study, the gene of d-amino acid oxidase (DAAO) was cloned and expressed in Escherichia coli. By coupling exogenous catalase (CAT), a biocatalytic cascade was constructed for synthesis of PPO in one pot. The bioprocess was optimized on a 300 mL scale reaction by one factor at a time optimization. The conversion of this biocatalytic cascade achieved 46.8% towards 400 mM DL-PPT within 4 h. These results indicated that DAAO could be applied to the large-scale bioproduction of PPO and provide a promising route for the asymmetric synthesis of L-PPT by bio-enzymatic methods using PPO as the substrate.
Method for preparing L-glufosinate-ammonium
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Paragraph 0033-0039, (2020/10/30)
The invention belongs to the field of organic synthesis, and particularly relates to a method for preparing L-glufosinate-ammonium (I) or salt thereof. A compound represented by formula (II) or a saltthereof reacts with a compound represented by formula (III), and no matter whether an intermediate is separated or not, a product obtained by the reaction is subjected to a hydrolysis reaction to obtain L-glufosinate-ammonium (I) or a salt thereof. Compared with an existing L-glufosinate-ammonium synthesis route, the method is a new chemical synthesis route, the steps are simple, the atom economyis high, an L-glufosinate-ammonium product with a high ee value can be obtained without chiral catalysis, and the method has a potential industrialization application value.
Preparation method of glufosinate-ammonium
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Paragraph 0034;0037-0038; 0042-0044; 0047-0048, (2020/06/30)
The invention discloses a preparation method of glufosinate-ammonium. The preparation method comprises the following steps that 1, in alkaline environment, 4-(hydroxymethyl phosphono)-2-carbonyl butyric acid (I) and a benzylamine solution react to produce 2-[( phenyl amino)-4-(methyl sodium phosphate)-sodium butyrate (II); 2, 2-[(phenyl amino)-4-(methyl sodium phosphate)-sodium butyrate (II) is subjected to acid hydrolysis to obtain glufosinate-ammonium (III). Compared with the prior art, the preparation method has the advantages that the conditions are mild; the yield of the glufosinate-ammonium is high; the purity is high.
Method for preparing L-glufosinate-ammonium
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Paragraph 0039; 0046-0047; 0050, (2020/09/23)
The invention relates to a method for preparing L-glufosinate-ammonium. Compared with an existing method, the method of the invention is a new chemical synthesis route, is simple in steps, easily available in raw materials and controllable in cost, can obtain the L-glufosinate-ammonium product with the high ee value without chiral catalysis, and has potential industrial application value.
Method for preparing L-glufosinate-ammonium
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Paragraph 0030; 0043-0045, (2020/09/23)
The invention relates to a method for preparing L-glufosinate-ammonium. Compared with an existing method, the method of the invention is a new chemical synthesis route, is simple in steps, easily available in raw materials and controllable in cost, can obtain the L-glufosinate-ammonium product with the high ee value without chiral catalysis, and has potential industrial application value.
Method for preparing L-glufosinate-ammonium
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Paragraph 0047; 0057-0059; 0065; 0075-0077, (2020/09/23)
The invention relates to a method for preparing L-glufosinate-ammonium. According to the method, cheap and easily available L-homoserine is used as an initial raw material, L-glufosinate-ammonium witha high ee value is prepared through a three-step reaction, chiral catalysis is not needed, the cost is low, and the method has a potential industrial application value.
