1991-86-2

Basic information

• Product Name: α-Methyl-D-tyrosine
• Synonyms: α-Methyl-D-tyrosine;D-2-Me-Tyr-OH
• CAS NO: 1991-86-2
• Molecular Weight: 0
• Mol File: 1991-86-2.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: α-Methyl-D-tyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: α-Methyl-D-tyrosine(1991-86-2)
• EPA Substance Registry System: α-Methyl-D-tyrosine(1991-86-2)

Safety Data

• Hazardous Substances Data: 1991-86-2(Hazardous Substances Data)

Usage

Description

α-Methyl-D-tyrosine is a non-natural, optically active amino acid derivative derived from the naturally occurring amino acid tyrosine. It is characterized by the presence of a methyl group at the alpha position and exhibits a D-configuration, making it a valuable compound in various applications due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
α-Methyl-D-tyrosine is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those with enantioselective properties. Its unique structure allows for the development of drugs with targeted effects, reducing potential side effects and improving overall efficacy.
Used in Enantioselective Hydrolysis:
α-Methyl-D-tyrosine is used as a chiral auxiliary in enantioselective hydrolysis of amino acids. This application is crucial in the production of enantiomerically pure compounds, which are essential in the pharmaceutical, agrochemical, and fragrance industries. The use of α-Methyl-D-tyrosine in this process helps to achieve high levels of enantioselectivity, leading to more efficient and effective synthesis of desired enantiomers.
Used in Research and Development:
α-Methyl-D-tyrosine is also utilized in research and development for the study of enzyme specificity, protein structure, and function. Its unique properties make it a valuable tool in understanding the mechanisms of various biological processes and can contribute to the development of new therapeutic strategies and drug candidates.

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Relevant articles and documents

A novel phenylalanine ammonia-lyase from Pseudozyma antarctica for stereoselective biotransformations of unnatural amino acids

A novel phenylalanine ammonia-lyase of the psychrophilic yeast Pseudozyma antarctica (PzaPAL) was identified by screening microbial genomes against known PAL sequences. PzaPAL has a significantly different substrate binding pocket with an extended loop (26 aa long) connected to the aromatic ring binding region of the active site as compared to the known PALs from eukaryotes. The general properties of recombinant PzaPAL expressed in E. coli were characterized including kinetic features of this novel PAL with L-phenylalanine (S)-1a and further racemic substituted phenylalanines rac-1b-g,k. In most cases, PzaPAL revealed significantly higher turnover numbers than the PAL from Petroselinum crispum (PcPAL). Finally, the biocatalytic performance of PzaPAL and PcPAL was compared in the kinetic resolutions of racemic phenylalanine derivatives (rac-1a-s) by enzymatic ammonia elimination and also in the enantiotope selective ammonia addition reactions to cinnamic acid derivatives (2a-s). The enantiotope selectivity of PzaPAL with o-, m-, p-fluoro-, o-, p-chloro- and o-, m-bromo-substituted cinnamic acids proved to be higher than that of PcPAL.

Organocatalytic Enantioselective Addition of α-Aminoalkyl Radicals to Isoquinolines

With a dual organocatalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer and under the irradiation with visible light, an enantioselective Minisci-type addition of α-amino acid-derived redox-active esters (RAEs) to isoquinolines has been developed. A variety of prochiral α-aminoalkyl radicals generated from RAEs were successfully introduced on isoquinolines, providing a range of valuable α-isoquinoline-substituted chiral secondary amines in high yields with good to excellent enantioselectivities.

Engineered Aminotransferase for the Production of d-Phenylalanine Derivatives Using Biocatalytic Cascades

d-Phenylalanine derivatives are valuable chiral building blocks for a wide range of pharmaceuticals. Here, we developed stereoinversion and deracemization biocatalytic cascades to synthesize d-phenylalanine derivatives that contain electron-donating or -withdrawing substituents of various sizes and at different positions on the phenyl ring with a high enantiomeric excess (90 to >99 % ee) from commercially available racemic mixtures or l-amino acids. These whole-cell systems couple Proteus mirabilis l-amino acid deaminase with an engineered aminotransferase that displays native-like activity towards d-phenylalanine, which we generated from Bacillus sp. YM-1 d-amino acid aminotransferase. Our cascades are applicable to preparative-scale synthesis and do not require cofactor-regeneration systems or chemical reducing agents.