25698-37-7

Usage

Uses

Used in Organic Chemistry Research:
(R)-AMINO-(3-CHLORO-PHENYL)-ACETIC ACID is used as a research compound for investigating its chemical properties and potential reactions. Its unique structure, featuring both an amino group and a chlorine atom, makes it a subject of interest for studying its reactivity and possible applications in organic synthesis.
Used in Pharmaceutical Development:
As a derivative of phenylacetic acid, (R)-AMINO-(3-CHLORO-PHENYL)-ACETIC ACID is used as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its chirality and functional groups may contribute to the development of new drugs with specific therapeutic effects.
Used in Material Science:
(R)-AMINO-(3-CHLORO-PHENYL)-ACETIC ACID's structural features may also make it a candidate for use in the development of new materials, such as polymers or other advanced materials, where its reactivity and stereochemistry could play a role in determining the material's properties.
(Note: The uses listed are speculative based on the information provided and the general knowledge of similar compounds. The actual applications may vary and are subject to ongoing research and development.)

Upstream product

• 67-66-3 chloroform 
• 587-04-2 m-Chlorobenzaldehyde 
• 71737-94-5 5-(m-chlorophenyl)hydantoin 
• 7292-71-9 2-(3-chlorophenyl)glycine 
• 93554-79-1 alpha-amino-(3-chlorophenyl)acetonitrile 
• 16273-37-3 3-chloromandelic acid 
• 2039-85-2 3-Chlorostyrene 

Downstream Products

• 7292-71-9 2-(3-chlorophenyl)glycine 

Relevant academic research and scientific papers

Investigation of Taniaphos as a chiral selector in chiral extraction of amino acid enantiomers

Finding chiral selector with high stereoselectivity to a variety of amino acid enantiomers remains a challenge and warrants further research. In this work, Taniaphos, a chiral ligand with rotatable spatial configuration, was employed as a chiral extractant to enantioseparate various amino acid enantiomers. Phenylalanine (Phe), homophenylalanine (Hphe), 4-nitrophenylalanine (Nphe), and 3-chloro-phenylglycine (Cpheg) were used as substrates to evaluate the extraction efficiency. The results revealed that Taniaphos-Cu exhibited good abilities to enantioseparate Phe, Hphe, Nphe, and Cpheg with the highest separation factors (α) of 3.13, 2.10, 2.32, and 2.14, respectively. Taniaphos-Cu is more conducive to combine with D-amino acid in extraction. The influences of pH, Taniaphos-Cu, and concentration and extraction temperature on extraction were comprehensively evaluated. The highest performance factors (pf) for Phe, Hphe, Nphe, and Cpheg at optimal extraction conditions were 0.08892, 0.1250, 0.09621, and 0.08021, respectively. The recognition mechanism between Taniaphos-Cu and amino acid enantiomers was discussed. The coordination interaction between Taniaphos-Cu and -COO?, π-π interaction between Taniaphos-Cu and amino acid enantiomers are important acting forces in chiral extraction. The steric-hindrance between -NH2 and -OH lead to Taniaphos-Cu-D-Phe is more stable than Taniaphos-Cu-L-Phe. This work provided a chiral extractant that has good abilities to enantioseparate various amino acid enantiomers.

Method for splitting 3-chlorine-phenylglycine enantiomers

The invention relates to the technical field of medicinal chemistry, in particular to a method for splitting 3-chlorine-phenylglycine enantiomers. The method for splitting the 3-chlorine-phenylglycineenantiomers comprises the steps that a diphosphine liga

Enantioselective liquid-liquid extraction of 3-chloro-phenylglycine enantiomers using (S,S)-DIOP as extractant

(S,S)-DIOP, a common catalyst used in asymmetric reaction, was adopted as chiral extractant to separate 3-chloro-phenylglycine enantiomers in liquid-liquid extraction. The factors affecting extraction efficiency were studied, including metal precursors, o

One-Pot Enantioselective Synthesis of d-Phenylglycines from Racemic Mandelic Acids, Styrenes, or Biobased l-Phenylalanine via Cascade Biocatalysis

Enantiopure d-phenylglycine and its derivatives are an important group of chiral amino acids with broad applications in thepharmaceutical industry. However, the existing synthetic methods for d-phenylglycine mainly rely on toxic cyanide chemistry and multistep processes. To provide green and safe alternatives, we envisaged cascade biocatalysis for the one-pot synthesis of d-phenylglycine from racemic mandelic acid, styrene, and biobased l-phenylalanine, respectively. Recombinant Escherichia coli (LZ110) was engineered to coexpress four enzymes to catalyze a 3-step reaction in one pot, transforming mandelic acid (210 mM) to give enantiopure d-phenylglycine in 29.5 g L?1 (195 mM) with 93% conversion. Using the same whole-cell catalyst, twelve other d-phenylglycine derivatives were also produced from the corresponding mandelic acid derivatives in high conversion (58–94%) and very high ee (93–99%). E. coli (LZ116) expressing seven enzymes was constructed for the transformation of styrene to enantiopure d-phenylglycine in 80% conversion via a one-pot 6-step cascade biotransformation. Twelve substituted d-phenylglycines were also produced from the corresponding styrene derivatives in high conversion (45–90%) and very high ee (92–99%) via the same cascade reactions. A nine-enzymeexpressing E. coli (LZ143) was engineered to transform biobased l-phenylalanine to enantiopure d-phenylglycine in 83% conversion via a one-pot 8-step transformation. Preparative biotransformations were also demonstrated. The high-yielding synthetic methods use cheap and green reagents (ammonia, glucose, and/or oxygen), and E. coli whole-cell catalysts, thus providing green and useful alternative methods for manufacturing d-phenylglycine. (Figure presented.).

Practical and convenient enzymatic synthesis of enantiopure α-amino acids and amides

Catalyzed by the nitrile hydratase and the amidease in Rhodococcus sp. AJ270 cells under very mild conditions, a number of α-aryl- and α-alkyl-substituted DL-glycine nitriles 1 rapidly underwent a highly enantioselective hydrolysis to afford D-(-)-α-amino acid amides 2 and L-(+)-α-amino acids 3 in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the biotransformations of nitriles originated from the combined effects of a high L-enantioselective amidase and a low enantioselective nitrile hydratase. The influence of the substrates on both reaction efficiency and enantioselectivity was also discussed in terms of steric and electronic effects. Coupled with chemical hydrolysis of D-(-)-α-phenylglycine amide, biotransformation of DL-phenylglycine nitrile was applied in practical scale to produce both D- and L-phenylglycines in high optical purity.

Highly efficient and enantioselective synthesis of L-arylglycines and D-arylglycine amides from biotransformations of nitriles

Under very mild conditions, the Rhodococcus sp. AJ270-catalysed biotransformation of arylglycine nitriles 1, prepared easily from the reaction of substituted benzaldehydes, ammonium chloride and potassium cyanide, proceeded efficiently to produce optically active D-arylglycine amides 2 and L-arylglycines 3 in excellent yields with enantiomeric excesses higher than 99%.

Production of ring-substituted D-phenylglycines by microbial or enzymatic hydrolysis/deracemisation of the corresponding DL-hydantoins

A series of 17 ring-mono and -disubstituted D-phenylglycine derivatives was prepared in high enantiomeric purity by enzymatic hydrolysis and deracemisation of the corresponding DL-hydantoins, using D-hydantoinase activities of microorganisms or purified enzymes, followed by diazotation of the resulting N-carbamyl-D-amino acids. No significant L-hydantoinase activity was found to produce the corresponding L-enantiomers.

ASYMMETRIC INDUCTIVE SYNTHESIS OF α-AMINOARYLACETIC ACIDS IN CHIRAL MICELLAR SYSTEM

In the micellar solution of chiral surfactant N-hexadecyl-N-methylephedrine bromide, seven α-aminoarylacetic acids were synthesized from corresponding aldehydes, the e.e.percent being about 28percent.