N-[3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]-L-histidine contains a phthalimide-linked side chain that alters electronic and steric properties. Researchers explore its hydrogen-bond networks, aromatic interactions, and conformational constraints. The modified histidine supports synthetic diversification and mechanistic analysis.
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CAT No: R2497
CAS No:7389-97-1
Synonyms/Alias:L-Histidine, N-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxopropyl]- (Polaprezinc Impurity 8);7389-97-1;L-Histidine, N-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxopropyl]-;(2S)-2-[3-(1,3-dioxoisoindol-2-yl)propanoylamino]-3-(1H-imidazol-5-yl)propanoic acid;N-[3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]-L-histidine;(S)-2-(3-(1,3-Dioxoisoindolin-2-yl)propanamido)-3-(1H-imidazol-4-yl)propanoic acid;DTXSID60569325;(2S)-2-[3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanamido]-3-(1H-imidazol-4-yl)propanoic acid;
N-[3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]-L-histidine is a synthetic peptide derivative that incorporates a phthalimide-protected moiety conjugated to the side chain of L-histidine. As a structurally modified amino acid, it holds particular significance in peptide chemistry, enabling researchers to explore novel functionalities and protective strategies in peptide synthesis. The presence of both the phthalimide group and the histidine residue imparts unique chemical and physicochemical properties, making this compound relevant for advanced studies in peptide modification, structure-activity relationship analysis, and the development of specialized peptide-based tools for biochemical investigations.
Peptide synthesis: In solid-phase peptide synthesis (SPPS) and solution-phase peptide assembly, N-[3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]-L-histidine serves as a valuable building block for introducing protected histidine residues or for site-specific modifications. The phthalimide group acts as a temporary protecting group, safeguarding the amino functionality during chain elongation and preventing unwanted side reactions. Its use facilitates the construction of complex peptide sequences, especially when selective deprotection strategies are required to access free amine groups at precise stages of synthesis.
Peptide modification studies: The compound is instrumental in research focused on histidine side-chain derivatization and post-synthetic modification of peptides. By incorporating a phthalimide-protected propanoyl moiety onto histidine, researchers can investigate the effects of such modifications on peptide folding, stability, and biological recognition. This capability is particularly valuable when studying the structure-activity relationships of histidine-rich peptides or designing analogs with altered physicochemical or binding properties.
Chemical biology tool development: The unique structure of this histidine derivative makes it a useful component in the design of chemical probes and affinity tags. The protected amine functionality can be selectively revealed or further functionalized, enabling the creation of site-specific labels or reactive handles for conjugation to reporter groups, surfaces, or other biomolecules. Such applications are crucial in protein engineering, molecular labeling, and the development of peptide-based affinity reagents for use in biochemical assays.
Enzyme substrate design: Researchers utilize N-[3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]-L-histidine in the synthesis of tailored substrates for protease and peptidase studies. The presence of a modified histidine residue allows for the generation of substrates with altered cleavage profiles or resistance to enzymatic hydrolysis, thereby enabling the detailed investigation of enzyme specificity, catalytic mechanisms, and inhibition. These studies contribute to a deeper understanding of histidine-dependent enzymatic processes in biological systems.
Analytical method development: The compound's distinct chemical features make it suitable for use as a reference standard or internal control in chromatographic and mass spectrometric analyses of peptides and peptide derivatives. Its defined structure and modifiable functional groups facilitate method validation, instrument calibration, and the assessment of analytical sensitivity and specificity in complex peptide mixtures. Such applications are essential for ensuring robust and reliable results in peptide research and quality control environments.
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