73679-07-9

Basic information

• Product Name: Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2R)-
• Synonyms: D-glufosinate;D-phosphinothricin;(R)-2-Amino-4-(hydroxy-methyl-phosphinoyl)-butyric acid;(-)-phosphinothricin;D-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid
• CAS NO: 73679-07-9
• Molecular Formula: C5H12NO4P
• Molecular Weight: 181.128
• Mol File: 73679-07-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2R)-(73679-07-9)
• EPA Substance Registry System: Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2R)-(73679-07-9)

Safety Data

• Hazardous Substances Data: 73679-07-9(Hazardous Substances Data)

Upstream product

• 79778-02-2 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid 
• 1015254-38-2 L-2-benzylamino-4-(methoxymethylphosphinyl)-propionitrile 
• 63314-88-5 vinylmethylphosphinic acid methyl ester 
• 113890-30-5 2-((E)-((1S,2S,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylidene)amino) acetate 
• 127593-79-7 ethyl 2-((1R,2R,5R)-2-hydroxypinan-3-imino)glycinate 
• 90473-01-1 (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate 
• 90473-00-0 ethyl 2-((S,2S,5S)-2-hydroxypinan-3-imino)glybioncin C 
• 78342-42-4 (S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine 
• 109902-76-3 isobutyl 2-chloroethyl-methylphosphinate 
• 109838-85-9 (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine 

Relevant articles and documents

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 %).

Asymmetric Synthesis of (+)-Phosphinothricin and Related Compounds by the Michael Addition of Glycine Schiff Bases to Vinyl Compounds

(S)-(+)-Phosphinothricin was prepared in good optical yield by th Michael addition of chiral glycine Schiff base derived from (S)-2-hydroxy-3-pinanone to vinyl phosphorus compound. (R)-(-)-Phosphinothricin, an enantiomeric isomer, can also be prepared from the same chiral glycine Schiff base by choosing suitable reaction temperature.

ASYMMETRIC SYNTHESIS OF (+)-PHOSPHINOTHRICIN and (+)-2-AMINO-4-PHOSPHONOBUTYRIC ACID

Asymmetric synthesis of (+)-phosphinothricin, (+)-2-amino-4-phosphono-butyric acid, and their enantiomers has been achieved by the Michael addition of chiral glycine Schiff bases to vinyl phosphorus compounds.