35597-44-5

Usage

Uses

Used in Agriculture:
Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)is used as a herbicide for controlling annual weeds and grasses. Its application helps in managing unwanted plant growth, thereby improving crop yield and quality.

InChI:InChI=1/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)/t4-/m0/s1

Upstream product

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• 109902-76-3 isobutyl 2-chloroethyl-methylphosphinate 
• 63314-88-5 vinylmethylphosphinic acid methyl ester 
• 90473-00-0 ethyl 2-((S,2S,5S)-2-hydroxypinan-3-imino)glybioncin C 
• 90473-01-1 (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate 
• 113890-30-5 2-((E)-((1S,2S,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylidene)amino) acetate 
• 85178-62-7 L-Desmethylphosphinothricin 
• 51276-47-2 DL-homoalanin-4-yl(methyl)phosphinic acid 
• 56-86-0 L-glutamic acid 
• 79778-02-2 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid 

Relevant academic research and scientific papers

AN EFFICIENT ASYMMETRIC SYNTHESIS OF BOTH ENANTIOMERS OF PHOSPHINOTHRICIN

An efficient synthesis of both enantiomers of phosphinothricin 1 by alkylation of metalated chiral bis-lactim ethers is described.

Biocatalytic asymmetric synthesis of L-phosphinothricin using a one-pot three enzyme system and a continuous substrate fed-batch strategy

Transamination catalyzed by an aminotransferase is becoming a key tool for the production of chiral amine pharmaceuticals and agrochemicals owing to its excellent enantioselectivity and green credentials. To overcome the unfavorable thermodynamic equilibrium and the inhibition by the byproduct α-ketoglutaric acid in the transamination of 2-oxo-4-[(hydroxy)(methyl)phosphinoyl]butyric acid (PPO) to form the promising herbicide L-phosphinothricin (L-PPT), a tri-enzymatic cascade reaction system was developed by combining a robust glutamate dehydrogenase to recycle the byproduct to the amino donor L-glutamate in situ, together with a cofactor recycling process catalyzed by an alcohol dehydrogenase. Moreover, a continuous substrate fed-batch strategy was employed to alleviate the decomposition of PPO and applied to scale-up the cascade reaction to 90 L, yielding 111.4 g/L (615.4 mM) L-PPT in 99.7% yield and >99.9% ee with an productivity of 15.9 g/L?h. This combination of improved biocatalyst system and process engineering should prove to be economically competitive for industrial applications.

Efficient racemization of N-phenylacetyl-D-glufosinate for L-glufosinate production

Most amino acids contain chiral centres and exist as both D-enantiomer and L-enantiomer. The optically pure enantiomer is often more valuable than the racemate. Enzymatic resolution provides an effective strategy to obtain optically pure amino acids but often results in large amounts of unwanted isomer. In this study, optically pure L-glufosinate (L-PPT) was obtained by coupling amidase-mediated hydrolysis of N-phenylacetyl-D,L-glufosinate with racemization of N-phenylacetyl-D-glufosinate (NPDG), which exclusively exhibits effective herbicidal properties compared with its D-enantiomer. To improve the yield of L-PPT, the racemization reaction conditions were optimized, and through single-factor experiments, the optimal reaction temperature, reaction time, and mole ratio of phenylacetic acid to NPDG were determined to be 150°C, 30?minutes, and 1.5, respectively. The response surface methodology was applied to further optimize the racemization conditions, and the final yield of L-PPT reached 96.13% with optimum reaction temperature of 154°C, reaction time of 23?minutes, and phenylacetic acid/NPDG mole ratio of 1.7, respectively. Moreover, adding a small amount of acetic anhydride further raised the yield of L-PPT to 97.02%.

A Single-Transaminase-Catalyzed Biocatalytic Cascade for Efficient Asymmetric Synthesis of l-Phosphinothricin

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 %).

L-GLUFOSINATE INTERMEDIATE AND L-GLUFOSINATE PREPARATION METHOD

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.

Preparation method of glufosinate-ammonium

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

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

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.

Method for preparing L-glufosinate-ammonium

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

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.