33605-72-0

Basic information

• Product Name: 1-methyl 3-phenyl-N-[N-[(phenylmethoxy)carbonyl]-L-alpha-aspartyl]-L-alaninate
• Synonyms: 1-methyl 3-phenyl-N-[N-[(phenylmethoxy)carbonyl]-L-alpha-aspartyl]-L-alaninate;N-benzyloxycarbonyl-aspartylphenylalanine methyl ester;N-(N-Benzyloxycarbonyl-L-α-aspartyl)-L-phenylalanine 1-methyl ester;N-Carbobenzoxy-L-Asp-L-Phe-OMe;N-Cbz-Asp-Phe-OMe;ZAPM;L-Phenylalanine, N-[N-[(phenylMethoxy)carbonyl]-L-a-aspartyl]-, 1-Methyl ester
• CAS NO: 33605-72-0
• Molecular Formula: C₂₂H₂₄N₂O₇
• Molecular Weight: 428.43516
• EINECS: 251-588-2
• Mol File: 33605-72-0.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 686.7°Cat760mmHg
• Flash Point: 369.1°C
• Appearance: /
• Density: 1.29g/cm³
• CAS DataBase Reference: 1-methyl 3-phenyl-N-[N-[(phenylmethoxy)carbonyl]-L-alpha-aspartyl]-L-alaninate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl 3-phenyl-N-[N-[(phenylmethoxy)carbonyl]-L-alpha-aspartyl]-L-alaninate(33605-72-0)
• EPA Substance Registry System: 1-methyl 3-phenyl-N-[N-[(phenylmethoxy)carbonyl]-L-alpha-aspartyl]-L-alaninate(33605-72-0)

Safety Data

• Hazardous Substances Data: 33605-72-0(Hazardous Substances Data)

Usage

General Description

1-methyl 3-phenyl-N-[N-[(phenylmethoxy)carbonyl]-L-alpha-aspartyl]-L-alaninate is a chemical compound that is a derivative of L-alanine and L-alpha-aspartyl. It is often used as an intermediate in the synthesis of various drugs and pharmaceuticals. 1-methyl 3-phenyl-N-[N-[(phenylmethoxy)carbonyl]-L-alpha-aspartyl]-L-alaninate has potential applications in the pharmaceutical industry due to its ability to act as a building block for the production of novel drugs. Additionally, its unique structure and properties make it a valuable tool for research and development in the pharmaceutical and biotechnology fields.

Upstream product

• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 4515-23-5 N-benzyloxycarbonyl-L-aspartic acid anhydride 
• 1152-61-0 N-Cbz-L-Asp 
• 1154041-24-3 C₂₅H₂₈N₂O₇ 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 4515-21-3 N-benzyloxycarbonylaspartic acid 
• 27446-39-5 N-[N-[(phenylmethoxy)carbonyl]-L-α-aspartyl]-L-phenylalanine 4-(1,1-dimethylethyl) 1-methyl ester 
• 5619-07-8 methyl 2-amino-3-phenylpropanoate hydrochloride 
• 88966-25-0 N-benzyloxycarbonyl-L-aspartic anhydride 
• 100101-48-2 (S)-3-Benzyloxycarbonylamino-N-((Z)-1-methoxycarbonyl-2-phenyl-vinyl)-succinamic acid 
• 68802-01-7 N-benzyloxycarbonyl-L-aspartyl-L-phenylalanine methyl ester-L-phenylalanine methyl ester complex 
• 1152-61-0 2-Benzyloxycarbonylamino-succinic acid 
• 15028-44-1 DL-phenylalanine methyl ester 

Downstream Products

• 1154041-21-0 (Nα-benzyloxycarbonyl-Nγ-(β-D-glucopyranosyl)-L-asparaginyl)-L-phenylalanine methyl ester 
• 1154041-22-1 (Nα-benzyloxycarbonyl-Nγ-{4-(β-D-glucopyranosyl)-β-D-glucopyranosyl}-L-asparaginyl)-L-phenylalanine methyl ester 
• 1154041-23-2 (Nα-benzyloxycarbonyl-Nγ-{4-(α-D-glucopyranosyl)-β-D-glucopyranosyl}-L-asparaginyl)-L-phenylalanine methyl ester 
• 110622-44-1 L-Asp(L-Ala-OH)-L-Phe-OMe 
• 27446-39-5 N-[N-[(phenylmethoxy)carbonyl]-L-α-aspartyl]-L-phenylalanine 4-(1,1-dimethylethyl) 1-methyl ester 
• 22839-47-0 L-Asp-L-Phe-OMe 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 1152-61-0 N-Cbz-L-Asp 
• 130385-20-5 Z-L-Asp(L-Ala-OBzl)-L-Phe-OMe 

Relevant articles and documents

High isolated yields in thermolysin-catalysed synthesis of Z-L-aspartyl-L-phenylalanine methyl ester in toluene at controlled water activity

Z-L-Aspartyl-L-phenylalanine methyl and ethyl esters were synthesised enzymatically in toluene by means of the zinc protease thermolysin adsorbed onto Celite R-640, which is a porous support able to control the hydration of the protein. The conversion of the two derivatised amino acids into the desired products was complete, leading to >90% isolated yields. Moreover, working with equimolar concentrations of the reactants no purification steps were required. Thermolysin adsorbed onto Celite R-640 is shown to be a practical tool to synthesise biologically active peptides in organic media.

Enzymatic peptide synthesis in organic solvent with different zeolites as immobilization matrixes

A series of zeolite immobilized α-chymotrypsin and thermolysin with microporous Y zeolites (HY, NH4, NaY) and mesoporous dealuminized DAY zeolites (HDAY, HNH4DAY) as matrixes have been prepared to catalyze peptide bond formation in organic solvents for the first time. The results indicated that most zeolite immobilized enzymes were active for peptide syntheses in organic media, and still had catalytic activity to some extent after being reused five times. According to the results, the immobilization effect of microporous Y zeolite was better than that of mesoporous DAY zeolite, suggesting that microporous Y zeolite can form more powerful hydrogen bonds with enzyme molecules since there are more hydroxyl groups on the Y zeolite than on the DAY zeolite. In addition, the influences of some reaction conditions such as reaction time and water content of the solvent on the enzymatic peptide synthesis were also studied and optimized. For the two kinds of proteases, NH4Y zeolite did not show its advantages for thermolysin, but was more suitable for α-chymotrypsin as an immobilization matrix. 2000 Elsevier Science Ltd.

Papain-Catalyzed Synthesis of Aspartame Precursor in Biphasic System

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Functional Capsule Membranes. Part 29. Thermolysin-immobilized Capsule Membranes as Bioreactors in the Synthesis of a Dipeptide (Precursor of Aspartame) in an Organic Solvent

Thermolysin (TLN) was covalently immobilized onto a large, ultrathin nylon capsule membrane grafted with poly- using glutaraldehyde.When the TLN-immobilized capsule containing a buffer solution (pH 7) in the inner aqueous phase was immersed in a chloroform solution of N-benzyloxycarbonyl-L-aspartic acid (Z-L-Asp) and L-phenylalanine methyl ester (L-PheOMe) with shaking at 40 deg C, the dipeptide (Z-L-Asp-L-PheOMe) was produced efficiently in the outer chloroform solution.From the Lineweaver-Burk plot, condensation in the aqueous-organic solvent involves initial binding of Z-L-Asp to the enzyme to form the Z-L-Asp-enzyme complex and then attack by L-PheOMe on the complex as the rate-determining step to form the peptide linkage.The TLN-capsule system can be used repeatedly without denaturation of protein structures by organic solvents because the enzyme on the capsule membrane is protected by buffer solutions coming from the inside.The enzyme-immobilized capsule membrane is a new bioreactor in aqueous-organic heterophases.

Biocatalytic properties of thermolysin immobilized on polyvinyl alcohol cryogel

Preparations with different contents of thermolysin were obtained by the immobilization of the enzyme on granulated polyvinyl alcohol cryogel. Their activity and stability in an aqueous medium and in mixtures of polar organic solvents of different composition were investigated. The catalytic properties of the preparations in reactions of peptide bond formation were studied, and the optimal amount of the biocatalyst, the concentrations of initial reagents, and the ratios of organic solvents and water necessary for effective enzymatic peptide synthesis catalyzed by immobilized thermolysin were determined. A series of peptides of the general formula Z-Ala-Ala-Xaa-pNA, where Xaa = Leu, Ile, Phe, Val, or Ala, were synthesized, and the immobilized enzyme was shown to retain substrate specificity in an organic medium.

Bromelain catalyzed synthesis of peptides in organic solvent

For the first time, immobilized bromelain was shown to maintain high catalytic activity in organic solvent and to form peptide bonds. It requires only 7 hours to obtain Cbz-Gly-L-Leu-OMe in 85% yield. The precursor of aspartame (Cbz-L-Asp-L-Phe-OMe) and other dipeptides were also synthesized by this method.