Methyl 2-(2-amino-3-phenylpropanamido)acetate is a small phenylalanine-derived amide ester useful as a chiral building block. The molecule retains an amino group for further coupling and an ester for hydrolysis or derivatization. Researchers examine its conformational preferences and reactivity in peptide or peptidomimetic synthesis. Applications include fragment-based design, stereochemical probes, and linker development.
CAT No: R2377
CAS No:186432-27-9
Synonyms/Alias:186432-27-9;methyl 2-(2-amino-3-phenylpropanamido)acetate;NSC522620;SCHEMBL6162382;LMMCSPQKCDZVTC-UHFFFAOYSA-N;AKOS005948752;NSC-522620;methyl2-(2-amino-3-phenylpropanamido)acetate;EN300-296242;(2-amino-3-phenyl-propionylamino)-acetic acid methyl ester;
Methyl 2-(2-amino-3-phenylpropanamido)acetate, also known by its systematic name or as a methyl ester derivative of a phenylalanine-based dipeptide, is a versatile carbohydrate compound frequently employed in biochemical and pharmaceutical research. Characterized by the presence of both amino and ester functional groups, this molecule serves as a valuable synthetic intermediate due to its structural features, which allow for further chemical modifications. The phenylalanine moiety confers unique chiral properties, making the compound particularly useful in stereoselective synthesis and studies involving peptide analogues. Its solubility and reactivity under mild conditions further enhance its applicability in various laboratory settings, supporting a wide range of scientific investigations.
Peptide Synthesis: Methyl 2-(2-amino-3-phenylpropanamido)acetate is widely utilized as a building block in the synthesis of custom peptides and peptide mimetics. Its structure, featuring both an amide and a protected carboxyl group (as the methyl ester), facilitates stepwise elongation of peptide chains during solid-phase or solution-phase peptide synthesis. Researchers leverage this compound to introduce phenylalanine residues into peptide sequences, enabling the investigation of structure-activity relationships, protein-protein interactions, and the development of novel bioactive peptides for research applications.
Pharmaceutical Research: The methyl ester derivative is frequently employed as an intermediate in the design and synthesis of small-molecule drug candidates. Its chemical backbone, which incorporates both aromatic and amino acid functionalities, allows medicinal chemists to explore new scaffolds for enzyme inhibitors, receptor ligands, or molecular probes. By modifying the ester or amide groups, researchers can generate analogues with tailored pharmacokinetic or pharmacodynamic profiles, supporting the discovery and optimization of potential therapeutic agents in preclinical studies.
Chiral Synthesis: As a chiral compound derived from phenylalanine, methyl 2-(2-amino-3-phenylpropanamido)acetate plays a significant role in asymmetric synthesis. Its enantiomerically pure form is often used as a chiral auxiliary or starting material in the preparation of optically active molecules. This application is particularly important in the synthesis of pharmaceuticals and natural products, where stereochemistry can drastically influence biological activity. The compound's unique configuration enables the development of synthetic methodologies that yield products with high enantiomeric excess, thereby advancing the field of stereoselective organic chemistry.
Analytical Chemistry: In analytical laboratories, methyl 2-(2-amino-3-phenylpropanamido)acetate serves as a reference standard or derivatization agent for the qualitative and quantitative analysis of amino acids and peptides. Its distinctive structure and functional groups facilitate its detection by chromatographic and spectrometric techniques, aiding in the identification and characterization of related compounds in complex mixtures. This application supports the validation of synthetic routes, quality control of peptide products, and the elucidation of metabolic pathways in biochemical research.
Material Science: Researchers in material science employ this compound to design and synthesize novel polymeric materials with tailored properties. The presence of both aromatic and amino acid-derived functionalities enables the formation of functionalized polymers and hydrogels, which can be further modified for specific applications such as biosensors, drug delivery systems, or biocompatible coatings. By incorporating methyl 2-(2-amino-3-phenylpropanamido)acetate into polymer backbones, scientists can modulate physical, chemical, and biological properties, expanding the utility of these materials in advanced technological applications.
Chemical Biology: In the field of chemical biology, this methyl ester derivative is instrumental for the development of molecular probes and labeling reagents. Its reactivity and compatibility with peptide chemistry allow for the incorporation of bioorthogonal handles or reporter groups, facilitating the study of biological processes at the molecular level. Researchers utilize such modified compounds to investigate protein function, cellular pathways, and biomolecular interactions, thereby contributing to a deeper understanding of complex biological systems and the advancement of molecular life sciences.
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