L-Aspartyl-L-phenylalanine is a dipeptide inhibitor of angiotensin-converting enzyme (ACE) and a metabolite of the synthetic non-caloric sweetener aspartame. It is formed from aspartame by intestinal intracellular esterases. L-Aspartyl-L-phenylalanine inhibits ACE with a Ki value of 11 µM for the rabbit enzyme. Serum levels of L-aspartyl-L-phenylalanine are positively associated with pancreatic ductal adenocarcinoma.
CAT No: 10-101-305
CAS No:13433-09-5
Synonyms/Alias:L-Aspartyl-L-phenylalanine;13433-09-5;H-ASP-PHE-OH;ASP-PHE;Aspartyl-phenylalanine;Aspartylphenylalanine;Demethylaspartame;l-a-aspartyl-l-phenylalanine;CHEBI:73830;L-alpha-Aspartyl-L-phenylalanine;(S)-3-Amino-4-(((S)-1-carboxy-2-phenylethyl)amino)-4-oxobutanoic acid;a-Aspartylphenylalanine;alpha-L-Aspartyl-L-phenylalanine;EINECS 236-557-3;(3S)-3-amino-4-[[(1S)-1-carboxy-2-phenylethyl]amino]-4-oxobutanoic acid;a-L-Aspartyl-L-phenylalanine;N-L-aspartyl-L-PhenylAlanine;CHEMBL170376;N-L-a-aspartyl-L-PhenylAlanine;N-L-alpha-aspartyl-L-PhenylAlanine;alpha-Aspartylphenylalanine;3-amino-N-(carboxyphenethyl)-Succinamic acid stereoisomer;3.Aspartame acid;3-amino-N-(a-carboxyphenethyl)-Succinamic acid stereoisomer;(S)-3-amino-4-((S)-1-carboxy-2-phenylethylamino)-4-oxobutanoic acid;MFCD00063155;.alpha.L-Aspartyl-L-phenylalanine;DF dipeptide;(3S)-3-amino-4-(((1S)-1-carboxy-2-phenylethyl)amino)-4-oxobutanoic acid;L-Aspartyl-L-phenylalanine; Aspartame Imp. B (EP); Aspartame Impurity B;alpha-Asp-Phe;D-F Dipeptide;L-a-Asp-L-phe;L-alpha-Asp-L-Phe;L-Asp-L-Phe;N-L-alpha-Aspartyl-3-phenyl-L-alanine;N-Aspartylphenylalanine;Asp-Phe, 96%;N-alpha-Aspartylphenylalanine;SCHEMBL135366;alphaL-Aspartyl-L-phenylalanine;N-L-alpha-Aspartylphenylalanine;Aspartate Phenylalanine dipeptide;Aspartate-Phenylalanine dipeptide;DTXSID20928570;YZQCXOFQZKCETR-UWVGGRQHSA-N;n-alpha-l-aspartyl-l-phenylalanine;13433-09-5 (free amine);Aspartic acid phenylalanine dipeptide;Aspartic acid-phenylalanine dipeptide;BDBM50049759;MSK001019;AKOS022180930;AS-46818;FA108005;1ST001019;CS-0044366;NS00014795;L-alpha-Aspartyl-L-phenylalanine Hydrochloride;F10617;N-L-alpha-Aspartyl-L-phenylalanine Hydrochloride;Q27144148;
Chemical Name:(3S)-3-amino-4-[[(1S)-1-carboxy-2-phenylethyl]amino]-4-oxobutanoic acid
Aspartylphenylalanine, commonly referred to as Asp-Phe, is a dipeptide composed of aspartic acid and phenylalanine linked by a peptide bond. As a member of the peptide compound category, Asp-Phe holds significant value in biochemical research due to its defined sequence and physicochemical properties. Its structure enables it to serve as a model substrate in enzymology, a building block in peptide synthesis, and a tool for probing protein-protein interactions. The presence of both acidic and aromatic side chains imparts unique characteristics that are exploited in various experimental and analytical contexts, making it a versatile reagent for laboratories focused on peptide science, analytical biochemistry, and molecular biology.
Peptide synthesis: Asp-Phe is widely employed as a reference dipeptide and intermediate in solid-phase peptide synthesis (SPPS) and solution-phase peptide assembly. Its well-characterized coupling and deprotection profiles make it an ideal candidate for optimizing synthetic protocols, validating reagent performance, and calibrating instrumentation. Researchers utilize this dipeptide to investigate coupling efficiencies, resin compatibility, and sequence-dependent side reactions, thereby enhancing the reliability and scalability of peptide production workflows.
Enzymatic specificity studies: As a defined dipeptide substrate, Asp-Phe is instrumental in assays evaluating the specificity and catalytic mechanisms of peptidases and proteases. By monitoring its hydrolysis, scientists can assess enzyme selectivity for aspartyl or phenylalanyl residues, elucidate substrate recognition motifs, and differentiate between exopeptidase and endopeptidase activities. These insights contribute to the broader understanding of proteolytic pathways, enzyme engineering, and inhibitor design.
Protein-protein interaction analysis: Due to its bifunctional side chains, Asp-Phe serves as a molecular probe in studies of non-covalent interactions, such as hydrogen bonding, π-π stacking, and electrostatic attraction. Its incorporation into model systems or peptide arrays allows researchers to dissect the contribution of specific dipeptide motifs to binding affinity, conformational stability, and molecular recognition events. Such investigations are critical for advancing knowledge of protein folding, signaling complexes, and ligand-receptor interactions.
Analytical method development: The unique physicochemical properties of Asp-Phe, including its solubility and chromatographic behavior, make it a valuable standard in the development and validation of analytical techniques. Laboratories utilize it to calibrate high-performance liquid chromatography (HPLC), capillary electrophoresis (CE), and mass spectrometry (MS) platforms for peptide detection, quantification, and purity assessment. Its defined retention time and fragmentation pattern facilitate method optimization and ensure reproducibility across analytical runs.
Structure-activity relationship (SAR) research: Incorporating Asp-Phe into peptide libraries or combinatorial arrays enables systematic exploration of how dipeptide sequences influence biological activity, stability, and molecular interactions. By substituting or modifying this motif, scientists can probe the structural determinants of bioactivity, optimize lead compounds, and map functional domains within larger peptides or proteins. These studies underpin rational design efforts in peptide-based research and biotechnological innovation.
2. Urinary Metabolites Associated with Blood Pressure on a Low-or High-Sodium Die
4. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes
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