Norophthalamic acid presents an aromatic-modified amino acid derivative valuable for probing electronic distribution within peptide environments. Its functional groups support hydrogen-bonding analysis and synthetic diversification. Researchers examine its conformational effects when incorporated into larger frameworks. Uses include structural chemistry, peptide modification, and ligand-scaffold development.
CAT No: R2350
CAS No:16305-88-7
Synonyms/Alias:Norophthalamic acid;gamma-Glu-ala-gly;Norophthalmic acid;16305-88-7;gamma-Glutamyl-alanyl-glycine;L-gamma-glutamyl-L-alanylglycine;1116-21-8;(2S)-2-amino-5-[[(2S)-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid;gamma-glutamylalanylglycine;CHEBI:143251;DTXSID40167505;Glycine, N-(N-L-gamma-glutamyl-L-alanyl)-;(2S)-2-AMINO-4-[[(1S)-1-(CARBOXYMETHYLCARBAMOYL)ETHYL]CARBAMOYL]BUTANOIC ACID;(2S)-2-amino-4-{[(1S)-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid;(2S)-2-amino-4-(((1S)-1-((carboxymethyl)carbamoyl)ethyl)carbamoyl)butanoic acid;(2S)-2-amino-5-(((2S)-1-(carboxymethylamino)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid;g-Glu-ala-gly;(2S)-2-Amino-4-(((1S)-1-((carboxymethyl)-C-hydroxycarbonimidoyl)ethyl)-C-hydroxycarbonimidoyl)butanoate;(2S)-2-Amino-4-{[(1S)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoate;g-Glutamylalanylglycine;SCHEMBL2690973;DTXCID9089996;NS00125092;N5-((S)-1-((Carboxymethyl)amino)-1-oxopropan-2-yl)-L-glutamine;BWS;
Norophthalamic acid is a synthetic organic compound that belongs to the class of phthalamic acid derivatives, characterized by its unique aromatic structure and functional amide group. As a non-proteinogenic molecule, it is not naturally occurring in biological systems but is valued for its chemical versatility and structural features that make it an important tool in biochemical and analytical research. Its distinctive molecular framework allows for specific interactions in various chemical environments, lending itself to a range of applications in experimental and industrial contexts. Norophthalamic acid's relevance extends to studies of amide bond chemistry, molecular recognition, and the development of novel analytical methodologies, positioning it as a useful reagent for researchers seeking to explore the properties and behaviors of aromatic amide systems.
Analytical chemistry: Norophthalamic acid is frequently utilized as a reference compound or calibration standard in chromatographic and spectroscopic analyses. Its well-defined structure and stability enable precise quantification and validation of analytical methods, particularly in high-performance liquid chromatography (HPLC) and mass spectrometry. Researchers leverage its predictable retention behavior and ionization properties to optimize separation protocols and ensure data accuracy when evaluating structurally related analytes or developing new detection techniques.
Synthetic intermediate: Due to its functionalized aromatic core and accessible amide group, norophthalamic acid serves as a valuable intermediate in organic synthesis. It can be employed in the preparation of more complex phthalimide or phthalic acid derivatives, which are relevant in the synthesis of dyes, pharmaceuticals, and specialty polymers. The compound's reactivity facilitates the introduction of additional substituents or the construction of heterocyclic frameworks, supporting the development of novel molecules for diverse chemical applications.
Structure-activity relationship studies: Norophthalamic acid is often incorporated into structure-activity relationship (SAR) investigations to probe the influence of aromatic amide motifs on biological or physicochemical properties. By systematically modifying its core structure or substituents, scientists can elucidate the role of specific functional groups in molecular recognition, binding affinity, or solubility. Such studies provide foundational insights for the rational design of new compounds with tailored properties for research or industrial use.
Material science research: The compound's robust aromatic backbone and amide linkage make it a candidate for exploring supramolecular assembly and intermolecular interactions in material science. Norophthalamic acid can participate in hydrogen bonding, π-π stacking, and other non-covalent interactions, which are critical in the design of advanced materials such as organic semiconductors, molecular crystals, or self-assembled monolayers. Its integration into experimental systems aids in understanding the fundamental principles governing the organization and behavior of functional organic materials.
Chemical education and method development: Norophthalamic acid is also utilized in academic and industrial laboratories as a model compound for teaching and method development. Its straightforward synthesis and well-characterized properties make it suitable for demonstrations of amide bond formation, aromatic substitution reactions, and spectroscopic analysis. By providing a reliable platform for hands-on experimentation, it enhances the practical training of students and supports the refinement of laboratory protocols across various disciplines.
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