3235-14-1

Basic information

• Product Name: Z-ALA-PHE-OME
• Synonyms: Z-ALA-PHE-OME;2-[2-(benzyloxycarbonylamino)propanoylamino]-3-phenyl-propionic acid methyl ester;methyl 3-phenyl-2-[2-(phenylmethoxycarbonylamino)propanoylamino]propanoate
• CAS NO: 3235-14-1
• Molecular Formula: C₂₁H₂₄N₂O₅
• Molecular Weight: 384.43
• Mol File: 3235-14-1.mol
• Article Data: 39

Chemical Properties

• Melting Point: 99-102 °C
• Boiling Point: 597°Cat760mmHg
• Flash Point: 314.9°C
• Appearance: /
• Density: 1.197g/cm³
• Vapor Pressure: 3.23E-14mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: -15°C
• PKA: 11.13±0.46(Predicted)
• CAS DataBase Reference: Z-ALA-PHE-OME(CAS DataBase Reference)
• NIST Chemistry Reference: Z-ALA-PHE-OME(3235-14-1)
• EPA Substance Registry System: Z-ALA-PHE-OME(3235-14-1)

Safety Data

• Hazardous Substances Data: 3235-14-1(Hazardous Substances Data)

Usage

General Description

Z-ALA-PHE-OME is a chemical compound that is composed of three amino acids - alanine, phenylalanine, and omega-methyl ester. It has the molecular formula C20H22N2O4 and a molecular weight of 350.39 g/mol. Z-ALA-PHE-OME is primarily used in the research and development of peptide synthesis and pharmaceuticals. It is also of interest in the study of biochemistry and the structure-function relationships of proteins. Additionally, Z-ALA-PHE-OME has potential applications in the field of drug design and medicinal chemistry, where it may be utilized as a precursor or building block in the creation of new therapeutic agents.

InChI:InChI=1/C21H24N2O5/c1-15(22-21(26)28-14-17-11-7-4-8-12-17)19(24)23-18(20(25)27-2)13-16-9-5-3-6-10-16/h3-12,15,18H,13-14H2,1-2H3,(H,22,26)(H,23,24)

Upstream product

• 1142-20-7 N-Cbz-Ala 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 76413-56-4 3-(N-benzyloxycarbonyl-L-alanyl)-1,3-thiazolidine-2-thione 
• 122751-37-5 Z-Ala-OPyCl 
• 112695-90-6 Z-Ala-OH 2,6-dichloro-4-sulfenyl ester potassium salt 
• 112695-89-3 Z-Ala-OH 2,6-dibromo-4-sulfenyl ester sodium salt 
• 112695-91-7 Z-Ala-OH 2-nitro-4-sulfenyl ester sodium salt 
• 26607-52-3 Cbz-Ala-OH*DCHA 
• 134303-58-5 3-(Z-Ala)-methylpyridinium iodide ester 
• 100445-34-9 (S)-2-Benzyloxycarbonylamino-propionic acid 6-trifluoromethyl-benzotriazol-1-yl ester 
• 2768-53-8 N-benzyloxycarbonyl-L-alanyl-L-phenylalanine 
• 159390-21-3 1,3-Bis-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-2-methyl-isourea 
• 125814-23-5 Z-L-Ala-NCA 

Downstream Products

• 65356-79-8 Cbz-Ala-Phe-Ala-NH₂ 
• 65118-56-1 Cbz-Ala-Phe-Leu-NH₂ 
• 79113-78-3 Z-Ala-Phe-Leu-OH 
• 145126-32-5 Cbz-Ala-Phe-Ala-pNA 
• 87023-74-3 Z-Ala-Phe-Val-NH₂ 
• 87831-90-1 Z-Ala-Phe-Gly-Ala-NH₂ 
• 87831-92-3 Z-Ala-Phe-Leu-Ala-NH₂ 
• 87831-91-2 Z-Ala-Phe-Ala-Ala-NH₂ 
• 87831-93-4 Z-Ala-Phe-Ile-Ala-NH₂ 
• 2768-53-8 N-benzyloxycarbonyl-L-alanyl-L-phenylalanine 
• 95617-89-3 Z-(S)-Ala-(S)-Phe-NH₂ 
• 40298-89-3 L-alanyl-L-phenylalanine methyl ester 
• 3235-15-2 N-benzyloxycarbonyl-L-alanyl-L-phenylalanyl hydrazide 
• 15180-22-0 (3S,6S)-3-methyl-6-(phenylmethyl)piperazine-2,5-dione 

Relevant articles and documents

Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow

Phosphine-mediated deoxygenative nucleophilic substitutions, such as the Mitsunobu reaction, are of great importance in organic synthesis. However, the conventional protocols require stoichiometric oxidants to trigger the formation of the oxyphosphonium i

Engineered Substrate for Cyclooxygenase-2: A Pentapeptide Isoconformational to Arachidonic Acid for Managing Inflammation

Beyond the conventional mode of working of anti-inflammatory agents through enzyme inhibition, herein, COX-2 was provided with an alternate substrate. A proline-centered pentapeptide isoconformational to arachidonic acid, which exhibited appreciable selectivity for COX-2, overcoming acetic acid- and formalin-induced pain in rats to almost 80%, was treated as a substrate by the enzyme. Remarkably, COX-2 metabolized the pentapeptide into small fragments consisting mainly of di- and tripeptides that ensured the safe breakdown of the peptide under in vivo conditions. The kinetic parameter Kcat/Km for COX-2-mediated metabolism of the peptide (6.3 × 105 M-1 s-1) was quite similar to 9.5 × 105 M-1 s-1 for arachidonic acid. Evidenced by the molecular dynamic studies and the use of Y385F COX-2, it was observed that the breakage of the pentapeptide has probably been taken place through H-bond activation of the peptide bond by the side chains of Y385 and S530.

Tandem deprotection/coupling for peptide synthesis in water at room temperature

A tandem deprotection/coupling sequence is reported for solution-phase peptide synthesis in water under micellar catalysis conditions using the designer surfactant TPGS-750-M. Cbz deprotection followed by peptide coupling in the presence of COMU and 2,6-lutidine afforded polypeptides containing up to 10 amino acid residues. A broad scope characterizes this new technology. No epimerization has been detected. The associated E Factors, as a measure of "greenness" and known to be extremely high for peptide couplings, have been reduced to less than 10 due to the step-economy and minimal amounts of organic solvent needed for product extraction.