2439-60-3

Basic information

• Product Name: N-methyl phenylalanine methyl ester
• Synonyms: N-methyl phenylalanine methyl ester
• CAS NO: 2439-60-3
• Molecular Weight: 193.246
• Mol File: 2439-60-3.mol
• Article Data: 23

Chemical Properties

• CAS DataBase Reference: N-methyl phenylalanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyl phenylalanine methyl ester(2439-60-3)
• EPA Substance Registry System: N-methyl phenylalanine methyl ester(2439-60-3)

Safety Data

• Hazardous Substances Data: 2439-60-3(Hazardous Substances Data)

Upstream product

• 195719-56-3 2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionic acid methyl ester 
• 19460-86-7 (N-methyl)-L-phenylalanine methyl ester hydrochloride 
• 100-52-7 benzaldehyde 
• 50-00-0 formaldehyd 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 203873-67-0 (S)-methyl 2-(2-nitrophenylsulfonamido)-3-phenylpropanoate 
• 108-98-5 thiophenol 
• 283611-40-5 N-methyl-N-(o-nitrobenzenesulfonyl)-L-phenylalanine methyl ester 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 2311-21-9 N-formyl-L-phenylalanine-methylester 
• 159090-52-5 (S)-methyl 2-[benzyl(methyl)amino]-3-phenylpropanoate 
• 1010385-04-2 C₁₈H₂₀ClNO₂ 
• 1010385-02-0 C₁₉H₂₃NO₃ 
• 1010385-00-8 C₁₉H₂₃NO₃ 

Downstream Products

• 94779-17-6 N-Boc-Phe-(N-Me)Phe-OMe 
• 74085-36-2 (S)-2-{[2-((R)-2-Benzyloxycarbonylamino-propionylamino)-acetyl]-methyl-amino}-3-phenyl-propionic acid methyl ester 
• 74085-21-5 Z-Tyr-D-Ala-Gly-MePhe-OMe 
• 139657-22-0 N-methyl-N-3,7>dec-2-yloxy)carbonyl>-(R)-tryptophyl>-(S)-phenylalanine methyl ester 
• 338462-77-4 (S)-N-(2-chloroethyl)-N-methylphenylalanine methyl ester 
• 463945-40-6 (S)-1-(3-Amino-propyl)-3-benzyl-4-methyl-piperazine-2,5-dione 
• 909108-78-7 (S)-2-{[(S)-2-((S)-2-{[(S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoyl]-methyl-amino}-3-methyl-butyrylamino)-4-methyl-pentanoyl]-methyl-amino}-3-phenyl-propionic acid methyl ester 
• 909109-71-3 (S)-2-[((S)-2-{(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 
• 909108-93-6 (S)-2-{[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-4-methyl-pentanoyl]-methyl-amino}-3-phenyl-propionic acid methyl ester 
• 909108-94-7 (S)-2-({(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-butyrylamino]-4-methyl-pentanoyl}-methyl-amino)-3-phenyl-propionic acid methyl ester 
• 915374-29-7 (S)-2-[((S)-2-Amino-4-methyl-pentanoyl)-methyl-amino]-3-phenyl-propionic acid methyl ester 

Relevant articles and documents

Toward the synthesis and improved biopotential of an n-methylated analog of a proline-rich cyclic tetrapeptide from marine bacteria

An N-methylated analog of a marine bacteria-derived natural proline-rich tetracyclopeptide was synthesized by coupling the deprotected dipeptide fragments Boc-L-prolyl-L-N-methylleucine-OH and L-prolyl-L-N-methylphenylalanine-OMe. A coupling reaction was accomplished utilizing N,N0-Dicyclohexylcarbodidimde (DCC) and 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC·HCl) as coupling agents and Triethylamine (TEA) or N-methylmorpholine (NMM) as the base in the presence of the racemization suppressing agent. This was followed by the cyclization of the linear tetrapeptide fragment under alkaline conditions. The structure of the synthesized cyclooligopeptide was confirmed using quantitative elemental analysis, FTIR (Fourier-transform infrared spectroscopy),1H NMR (Nuclear magnetic resonance spectroscopy),13C NMR, and mass spectrometry. From the bioactivity results, it was clear that the newly synthesized proline-rich tetracyclopeptide exhibited better anthelmintic potential against Megascoplex konkanensis, Pontoscotex corethruses, and Eudrilus eugeniae at a concentration of 2 mg/mL as well as improved antifungal activity against pathogenic dermatophytes Trichophyton mentagrophytes and Microsporum audouinii at a concentration of 6 μg/mL, as compared to non-methylated tetracyclopeptide. Moreover, N-methylated tetracyclopeptide displayed significant activity against pathogenic Candida albicans.

Postsynthetic Modification of Phenylalanine Containing Peptides by C-H Functionalization

New methods for peptide modification are in high demand in drug discovery, chemical biology, and materials chemistry; methods that modify natural peptides are particularly attractive. A Pd-catalyzed, C-H functionalization protocol for the olefination of phenylalanine residues in peptides is reported, which is compatible with common amino acid protecting groups, and the scope of the styrene reaction partner is broad. Bidentate coordination of the peptide to the catalyst appears crucial for the success of the reaction.

Preparation of the optically pure N-methyl amino ester method and product

The invention belongs to the field of organic synthesis of amino acids and discloses a method for preparing optically pure N-methyl amino-acid ester. The method comprises the following steps of carrying out esterification reaction on amino acid as a starting raw material and aldehyde to form an imine intermediate, carrying out reductive amination in the presence of palladium carbon, and carrying out hydrogenation and debenzylation to finally synthesize optically pure N-methyl amino-acid ester. The method has the advantages of simplicity in method, mild reaction conditions and good adaptability and side chains of D-type or L-type amino acid do not need to be protected.