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 specialized carbohydrate compound recognized for its unique structural properties and versatile reactivity, making it a valuable tool in both academic and industrial research settings. As a derivative within the broader class of sugar acids, norophthalamic acid features distinct functional groups that allow for selective chemical modifications and interactions. Its stability under various laboratory conditions and compatibility with a range of solvents make it particularly attractive for synthetic applications. Researchers appreciate norophthalamic acid for its role as a building block in the design and synthesis of more complex carbohydrate-based molecules, providing a foundation for innovation in multiple scientific disciplines.
Carbohydrate Synthesis: Norophthalamic acid serves as an essential intermediate in the assembly of complex oligosaccharides and glycoconjugates. Its well-defined structure allows for precise glycosylation reactions, facilitating the stepwise construction of carbohydrate chains with controlled stereochemistry. The compound's reactivity enables chemists to introduce specific modifications, such as the installation of protective groups or the incorporation of isotopic labels, which are crucial for studying carbohydrate function and metabolism in various biological contexts. By leveraging norophthalamic acid in synthetic pathways, researchers can efficiently generate libraries of carbohydrate derivatives for further investigation.
Glycobiology Research: In the field of glycobiology, norophthalamic acid is employed as a model substrate for probing enzyme specificity and mechanism. Its structural resemblance to naturally occurring sugar acids makes it suitable for studying the activity of glycosidases, glycosyltransferases, and other carbohydrate-processing enzymes. By incorporating norophthalamic acid into enzymatic assays, scientists can elucidate the roles of these enzymes in cellular processes, map substrate recognition sites, and identify potential inhibitors. This application contributes to a deeper understanding of carbohydrate metabolism and the regulation of glycan-mediated biological events.
Analytical Chemistry: Norophthalamic acid is utilized as a reference standard and derivatization agent in analytical chemistry workflows. Its defined chemical properties facilitate the calibration of chromatographic and spectroscopic techniques, such as high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy. When used as a derivatizing agent, norophthalamic acid can enhance the detectability and resolution of target analytes, improving the sensitivity and accuracy of quantitative analyses. This capability is particularly valuable in the quality control of carbohydrate-based materials and the characterization of complex biological samples.
Material Science: In material science, norophthalamic acid contributes to the development of novel biomaterials and functional polymers. Its ability to participate in covalent coupling reactions enables the creation of carbohydrate-containing surfaces, hydrogels, and nanomaterials with tailored properties. These materials find applications in areas such as biosensing, tissue engineering, and drug delivery, where the presence of carbohydrate moieties can modulate biocompatibility, cellular interactions, and molecular recognition. By incorporating norophthalamic acid into polymer matrices, researchers can design advanced materials with enhanced performance and specificity.
Chemical Biology Probes: The compound is also valuable in the design of chemical biology probes for investigating carbohydrate-mediated interactions. Norophthalamic acid derivatives can be functionalized with fluorescent tags, affinity handles, or photoactivatable groups, enabling the visualization and manipulation of glycan-binding events in vitro and in vivo. These probes facilitate the mapping of carbohydrate recognition patterns on proteins, cells, and tissues, advancing the understanding of glycan-mediated signaling pathways and cellular communication. Through such applications, norophthalamic acid supports the development of innovative tools for dissecting the complex roles of carbohydrates in biological systems.
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