49759-61-7

Basic information

• Product Name: 4-Methyl-D-phenylalanine
• Synonyms: (R)-2-AMINO-3-P-TOLYL-PROPIONIC ACID;RARECHEM BK PT 0070;D-4-METHYLPHE;D-4-METHYLPHENYLALANINE;H-P-ME-D-PHENYLALANINE;H-P-ME-D-PHE-OH;H-D-PHE(P-ME)-OH;H-D-PHE(4-ME)-OH
• CAS NO: 49759-61-7
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Phenylalanine [Phe, F];Unusual Amino Acids;Amino acids methyl、ethyl、t-butyl series;a-amino
• Mol File: 49759-61-7.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 323.5 °C at 760 mmHg
• Flash Point: 149.5 °C
• Appearance: /
• Density: 1.165 g/cm³
• Storage Temp.: Store at RT.
• CAS DataBase Reference: 4-Methyl-D-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyl-D-phenylalanine(49759-61-7)
• EPA Substance Registry System: 4-Methyl-D-phenylalanine(49759-61-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 49759-61-7(Hazardous Substances Data)

Usage

Uses

4-Methyl-D-phenylalanine is a derivative of D-Phenylalanine (P319410) and is used as a reagent in the synthesis of aminophenylpropanyl phosphate derivatives which can exhibit pin1 inhibitory activity.

Upstream product

• 1866-39-3 trans-p-methylcinnamic acid 
• 683809-83-8 2-amino-3-(4-fluoromethylphenyl)propionic acid 
• 1866-39-3 4-methylcinnamic acid 
• 4599-47-7 p-methylphenylalanine 
• 104-87-0 4-methyl-benzaldehyde 
• 38335-22-7 2-oxo-3-(p-tolyl)propanoic acid 
• 624-31-7 4-tolyl iodide 
• 3060-50-2 2,2-diphenylglycine 
• 6955-13-1 N-acetyl-4-methyl-phenylalanine 
• 49759-46-8 2-Benzyloxycarbonylamino-2-(4-methyl-benzyl)-malonic acid diethyl ester 
• 49759-54-8 2-Benzyloxycarbonylamino-3-p-tolyl-propionic acid ethyl ester 
• 49864-40-6 2-Benzyloxycarbonylamino-2-(4-methyl-benzyl)-malonic acid monoethyl ester 
• 104-81-4 4-Methylbenzyl bromide 
• 93634-54-9 (Z)-2-methyl-4-(4-methylbenzylidene)oxazol-5(4H)-one 

Downstream Products

• 923276-08-8 (S)-tert-butyl 2-amino-3-(p-tolyl)propanoate 
• 204260-38-8 (2S)-2-(9H-fluorene-9-ylmethoxycarbonylamino)-3-(4-methylphenyl)propanoic acid 
• 98698-22-7 (S)-7-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 39260-86-1 p-Methylphenethylamine hydrochloride 
• 1866-39-3 trans-p-methylcinnamic acid 
• 479064-87-4 (R)-3-amino-3-(4-methyl-phenyl)-propionic acid 
• 4599-47-7 p-methylphenylalanine 

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.

Ligand-Enabled β-C–H Arylation of α-Amino Acids Without Installing Exogenous Directing Groups

Herein we report acid-directed β-C(sp3)-H arylation of α-amino acids enabled by pyridine-type ligands. This reaction does not require the installation of an exogenous directing group, is scalable, and enables the preparation of Fmoc-protected unnatural amino acids in three steps. The pyridine-type ligands are crucial for the development of this new C(sp3)-H arylation.

A new type of chiral-pyridoxamines for catalytic asymmetric transamination of α-keto acids

A new type of chiral pyridoxamines bearing an adjacent chiral stereocenter has been developed via multi-step synthesis. The pyridoxamines displayed catalytic activity in asymmetric transamination of α-keto acids to give a variety of optically active amino acids in 27–78% yields with 34–62% ee's under very mild conditions. This work provides a synthetic strategy to construct new chiral pyridoxamines using bromopyridine 7 as a key synthon and also represents an early example of the applications of chiral pyridoxamines in asymmetric catalysis.