Methyl L-alpha-aspartyl-D-phenylalanate joins acidic aspartate with aromatic D-phenylalanine through a methyl ester, creating a chiral dipeptidyl ester system. The molecule is widely examined as a taste-modulating and flavor chemistry standard. Researchers study its conformational preferences, hydrolysis kinetics, and receptor-binding characteristics. Applications include food biochemistry, stereochemistry investigations, and peptide-derivative design.
CAT No: R2343
CAS No:22839-65-2
Synonyms/Alias:L-alpha-Aspartyl-D-phenylalanine methyl ester;22839-65-2;83860AQE03;Methyl L-alpha-aspartyl-D-phenylalanate;UNII-83860AQE03;alpha-L-Aspartyl-D-phenylalanine methyl ester;(3S)-3-amino-4-[[(2R)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid;D-Phenylalanine, N-L-alpha-aspartyl-, 1-methyl ester;.ALPHA.-L-ASPARTYL-D-PHENYLALANINE METHYL ESTER;SCHEMBL8761655;CHEMBL2110238;
Methyl L-alpha-aspartyl-D-phenylalanate is a synthetic dipeptide ester featuring an aspartic acid and a phenylalanine residue linked via a peptide bond, with methyl esterification at the C-terminus. As a member of the peptide compound category, it offers a valuable model for studying peptide bond formation, stereochemistry, and ester functionalities within biochemical and pharmaceutical research. Its defined stereochemistry and modifiable functional groups make it particularly useful for investigations into peptide structure-activity relationships, enzymatic hydrolysis, and the development of peptide-based delivery systems. The compound's unique configuration also supports its application as a reference standard and as an intermediate in synthetic peptide chemistry.
Peptide synthesis research: Methyl L-alpha-aspartyl-D-phenylalanate serves as a model substrate in the development and optimization of peptide synthesis methodologies. The presence of both L- and D- amino acid residues provides a platform for evaluating stereoselectivity and racemization during coupling reactions. Researchers utilize this dipeptide ester to assess the efficiency of various peptide coupling reagents, protecting group strategies, and conditions for esterification or amidation, thereby informing best practices for assembling more complex peptide sequences.
Enzymatic hydrolysis studies: The compound's methyl ester moiety and defined dipeptide structure make it highly suitable for probing the specificity and kinetics of proteolytic enzymes and esterases. By monitoring the hydrolysis of the peptide bond or the ester group, scientists can characterize enzyme selectivity, determine substrate preferences, and elucidate catalytic mechanisms. Such studies are fundamental for advancing knowledge in enzymology, protein digestion, and the design of enzyme inhibitors or substrates.
Peptide structure-activity relationship analysis: The inclusion of both L- and D- amino acids in methyl L-alpha-aspartyl-D-phenylalanate enables researchers to investigate the impact of chirality on peptide conformation and biological recognition. This compound is commonly deployed in conformational studies, circular dichroism experiments, and molecular modeling to understand how stereochemistry influences peptide backbone flexibility, side-chain orientation, and interaction with biological targets. Insights gained from these analyses support rational design of bioactive peptides and peptidomimetics.
Analytical method development: As a well-characterized dipeptide ester, the compound is frequently employed as a reference standard or calibration material in chromatographic and spectrometric analyses. Its defined physicochemical properties facilitate the validation of analytical methods such as HPLC, LC-MS, and capillary electrophoresis for peptide quantification, purity assessment, and impurity profiling. The use of such standards is critical for ensuring accuracy and reproducibility in peptide analytics across research and quality control laboratories.
Peptide delivery system evaluation: The methyl ester functionality and small size of this dipeptide make it a useful model for investigating peptide transport, stability, and release profiles in various delivery matrices. Researchers utilize it to study ester hydrolysis rates, membrane permeability, and encapsulation efficiency within polymeric carriers or liposomal formulations. These experiments inform the design and optimization of peptide-based delivery technologies, advancing the field of targeted molecular delivery and controlled release systems.
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