3235-14-1

Usage

Uses

Used in Pharmaceutical Research and Development:
Z-ALA-PHE-OME is used as a precursor in the synthesis of peptides and pharmaceuticals for its ability to contribute to the development of novel therapeutic agents.
Used in Biochemistry and Protein Structure-Function Studies:
Z-ALA-PHE-OME is utilized as a model compound in the study of biochemistry and the structure-function relationships of proteins, providing insights into the behavior and interactions of amino acids within biological systems.
Used in Drug Design and Medicinal Chemistry:
In the field of drug design and medicinal chemistry, Z-ALA-PHE-OME is used as a building block for the creation of new therapeutic agents, leveraging its structural properties to enhance the efficacy and specificity of drug candidates.

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 
• 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 
• 63-91-2 L-phenylalanine 
• 4132-86-9 N-benzyloxycarbonylalanine 

Downstream Products

• 65356-79-8 Cbz-Ala-Phe-Ala-NH₂ 
• 65118-56-1 Cbz-Ala-Phe-Leu-NH₂ 
• 1142-20-7 N-Cbz-Ala 
• 1639120-78-7 Cbz-Ala-Phe-His-OMe 
• 6769-85-3 Z-Ala-Phe-Met-OMe 
• 76146-32-2 Z--Ala--Phe--Val-OMe 
• 244206-40-4 C₂₅H₃₁N₃O₆ 
• 1639120-77-6 Cbz-Ala-Phe-Gly-OMe 
• 1639120-80-1 Cbz-Ala-Phe-Val-Leu-OMe 
• 1639120-91-4 Cbz-Ala-Phe-D-Val-Leu-OMe 
• 76146-33-3 Z--Ala--Phe--Val-OMe 

Relevant academic research and scientific papers

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

Synthesis of Dipeptide, Amide, and Ester without Racemization by Oxalyl Chloride and Catalytic Triphenylphosphine Oxide

An efficient triphenylphosphine oxide-catalyzed amidation and esterification for the rapid synthesis of a series of dipeptides, amides, and esters is described. This reaction is applicable to challenging couplings of hindered carboxylic acids with weakly

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.

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Toluene-4-sulfonate (DMT/NMM/TsO?) Universal Coupling Reagent for Synthesis in Solution

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO?), a representative member of the inexpensive and environmentally-friendly N-triazinylammonium family of sulfonates, has been found to be a very effective coupling reagent for the synthesis of amides, esters and peptides in solution. This study confirms the usefulness of DMT/NMM/TsO? for peptide synthesis in solution, starting from Z-, Fmoc-, and Boc-protected substrates as well as unnatural building blocks. Peptide synthesis with DMT/NMM/TsO? produced high yields, with high crude product purity and low risk of racemization. In all cases, stoichiometric amounts of reagents were used and the standard synthetic procedure, without the need for time-consuming optimization stages or expensive chromatographic purification. DMT/NMM/TsO? was also found to be very useful for the synthesis of oligopeptides using a fragment coupling strategy.

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.

9-Silafluorenyl Dichlorides as Chemically Ligating Coupling Agents and Their Application in Peptide Synthesis

A fundamentally simple, mild, and practical procedure for peptide bond formation is reported that employs a stoichiometric amount of easy-to-access 9-silafluorenyl dichlorides as the coupling agent. Without initial preactivation or elaboration of the carboxylic acid or amine termini of the amino acids, the developed reagent is proposed to act through an unprecedented chemical ligation mechanism, bringing the two coupling partners together before being subsequently eliminated. The desired amides or peptide bonds are thus furnished in good yields and with low to no epimerization.

A green route for the synthesis of a bitter-taste dipeptide combining biocatalysis, heterogeneous metal catalysis and magnetic nanoparticles

There is increasing demand for green technologies to produce high-solubility and low-toxicity compounds with potential application in the food industry. This study aimed to establish a clean, synthetic route for preparing the bitter-taste dipeptide Ala-Phe, a potential substitute for caffeine as a food additive. Synthesis of Z-Ala-Phe-OMe starting from Z-Ala-OH and HCl·Phe-OMe was catalysed by thermolysin at 50 °C in buffer (step 1). Z-Ala-Phe-OMe ester hydrolysis to give Z-Ala-Phe-OH at 37 °C in 30% acetonitrile/buffer was catalysed by α-bovine chymotrypsin (αCT), protease with esterase activity (step 2). Hydrogenation of Z-Ala-Phe to give the desired Ala-Phe was catalysed by C/Pd in methanol (step 3). Steps 2 and 3 were optimized by using the magnetically recoverable recycling enzyme Fe3O4@silica-αCT and the magnetically recoverable metal nanocatalyst Fe3O4@silica-Pd, respectively. This inspiring combination of technologies and the original results demonstrate the suitability of using enzymes, metal catalyst and magnetic nanoparticles for easy, economical, stereoselective, clean production of an important target compound. Besides, they add to the development of peptide chemistry and catalysis.

A one-pot saponification-coupling sequence suitable for C-terminus peptide elongation using lithium carboxylates

An efficient procedure has been developed for the saponification of common peptide esters, followed by straightforward coupling of the lithium carboxylate. Adding some water to the reaction medium gave faster saponification and did not interfere with the coupling reagent. As peptide chemistry constitutes a major application of the amidation reaction, amino acid substrates were chosen for this study, monitoring both yields and epimerization of the peptides obtained. Georg Thieme Verlag Stuttgart New York.

N-Triazinylammonium salts, a method of preparation and uses thereof

The invention provides inner quaternary N-triazinyl- ammonium salts of sulphonic acids, of the Formula 1, a method of preparation thereof and a use thereof as condensation reagents in condensation reactions.

The method of preparation of enantiomerically enriched products of condensation from racemic acids or acids of the low enentiomeric purity

The method of obtaining enantiomerically enriched condensation products consists of subjecting a racemic acid or an acid of low enantiomeric purity to the action of a condensing reagent - a chiral N-triazinylammonium tetrafluoroborate (formula 1), a chira