24593-49-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-4-methoxyphenylglycine is used as a chiral building block for the production of certain drugs, leveraging its stereoselective properties to ensure the desired biological activity and efficacy.
Used in Chemical Synthesis:
(R)-4-methoxyphenylglycine is utilized as a building block in the synthesis of various chemicals, contributing to the development of novel compounds with potential applications in different industries.
Used in Biological Research:
(R)-4-methoxyphenylglycine is employed in biological research to study its potential role in the development of new drugs and treatments for various conditions, further expanding its applications in the scientific field.

InChI:InChI=1/C9H11NO3/c1-13-8-4-2-7(3-5-8)10-6-9(11)12/h2-5,10H,6H2,1H3,(H,11,12)

Upstream product

• 74273-47-5 methyl 2-amino-2-(4-methoxyphenyl)acetate 
• 67-66-3 chloroform 
• 123-11-5 4-methoxy-benzaldehyde 
• 24593-76-8 D-(-)-(chloroacetyl)-2-(4-methoxyphenyl)glycine 
• 129505-13-1 (2R,2'R)-N-<2'-amino-2'-(4''-methoxyphenyl)acetyl>bornane-10,2-sultam hydrochloride 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 42456-26-8 2-amino-2-(4-methoxyphenyl)acetonitrile 
• 20714-90-3 4-Methoxymandelic acid 
• 637-69-4 4-Methoxystyrene 
• 24593-47-3 DL-N-(chloroacetyl)-2-(4-methoxyphenyl)glycine 
• 2540-53-6 2-(4-methoxyphenyl)glycine 
• 129505-11-9 (2R,2'R)-N-<2'-(hydroxyamino)-2'-(4''-methoxyphenyl)acetyl>bornane-10,2-sultam 
• 129505-04-0 (2R)-N-<(4-methoxyphenyl)acetyl>bornane-10,2-sultam 
• 76986-15-7 2-amino-2-(4-methoxyphenyl)acetamide 

Downstream Products

• 2540-53-6 2-(4-methoxyphenyl)glycine 

Relevant academic research and scientific papers

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.).

Large α-aminonitrilase activity screening of nitrilase superfamily members: Access to conversion and enantiospecificity by LC-MS

A high-throughput screening for the identification of nitrilases demonstrating activity towards alpha-aminonitriles is reported. A LC-MS assay giving access to both conversion and enantiospecificity was developed. 588 candidate enzymes were screened as cell lysates against six alpha-aminonitriles in 96-well microplates. The candidate enzymes were selected following two criteria, their sequence identity with a set of known nitrilases or their phylogenetic position among the nitrilase superfamily. Five enzymes were identified and found to hydrolyse alpha-aminonitrile into the corresponding alpha-aminoacid. The substrate range was found to be very narrow as only two different alpha-aminonitriles, 2-aminovaleronitrile and 2-amino-2- phenylacetonitrile, were found to be substrates. The biocatalytic capabilities of three enzymes were further investigated and the best result was obtained with an enzyme from Burkholderia xenovorans catalysing the enantiospecific hydrolysis of 2-aminovaleronitrile into (S)-norvaline with excellent conversion and enantiomeric excess.

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.

Asymmetric Synthesis of α-Amino Acids and α-N-Hydroxyamino Acids from N-Acylbornane-10,2-sultams: 1-Chloro-1-nitrosocyclohexane as a Practical +> Equivalent

Successive treatment of N-acylsultams 3 with sodium hexamethyldisilazide, 1-chloro-1-nitrosocyclohexane (1), and aq.HCl gave diastereoisomerically pure, crystalline N-hydroxyamino-acid derivatives 5.These were converted into various amino acids 7, N-hydroxyamino acids 8, and an N-Boc-amino acid 9. (S,S)-Isoleucine (17) and (S,S)-2-acetamido-3-phenylbutyric acid (23) were obtained from N-crotonoylsultam 15 via 1,4-addition of an organomagnesium or organocopper reagent followed by enolate 'amination' with 1.

Synthesis of Optically Active Arylglycines by Photolysis of Optically Active (β-Hydroxyamino) Carbene-Chromium(0) Complexes

Photolysis of chromium complexes having the optically active amino alcohol (1R,2S)-(-)- or (1S,2R)-(+)-2-amino-1,2-diphenylethanol as the amino group produced aryl-substituted oxazinones in good yield with reasonable diastereoselectivity.Facile separation of diastereoisomers followed by mild reductive cleavage produced several arylglycines, having either electron-donating or withdrawing groups on the aromatic ring, in good overall yield and with excellent enantiomeric excess.

Asymmetric synthesis of α-amino acids and α-N-hydroxyamino acids via electrophilic amination of bornanesultam-derived enolates with 1-chloro-1-nitrosocyclohexane

Successive treatment of N-acylsultams 3 with NaN(TMS)2, 1-chloro-1-nitrosocyclohexane (1) and 1N aq. HCl gave diastereomerically pure, crystalline N-hydroxyamino acid derivatives 4. Products 4 were converted to various amino acids 6, an N-BOC-amino acid 8 and to N-hydroxyamino acids 9. (S,S)-Isoleucine (16) was obtained from N-crotonoylsultam 13 via an organomagnesium-1,4-addition/enolate trapping process generating two stereogenic centers.

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.