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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Acetanilides
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Anilides Acetanilides

Acetamide-N,15N-Phenyl- (CAS No. 1449-75-8): A Versatile Isotopically Labeled Tool in Chemical Biology and Drug Discovery

The acetamide-N,15N-phenyl- compound, identified by CAS Registry Number 1449-75-8, represents a critical isotopically labeled reagent in contemporary chemical biology research. This compound is a derivative of N-acetylbenzamide where the nitrogen atom at position 2 of the acetyl group is substituted with the stable isotope ¹⁵N, creating a molecule with unique spectroscopic properties while retaining the structural and functional characteristics of its unlabelled counterpart. Its precise chemical formula, C₈H₉¹⁵N O, distinguishes it as a valuable tool for applications requiring isotopic tracing without altering pharmacological or biochemical behavior.

In recent years, this compound has gained prominence in studies targeting protein acetylation dynamics due to advancements in mass spectrometry-based proteomics. Researchers from the University of Cambridge demonstrated in a 2023 Nature Communications study that acetamide-N,15N-phenyl- serves as an ideal substrate for quantitative profiling of histone acetyltransferases (HATs). The ¹⁵N label enables precise detection of acetylation events through isotope dilution assays, providing unprecedented resolution in epigenetic studies without introducing detectable isotopic perturbations to cellular processes.

A groundbreaking application emerged in metabolic engineering research published in Angewandte Chemie (2023), where this compound was employed as a biosynthetic precursor to investigate enzyme catalytic mechanisms. By incorporating the ¹⁵N-labeled amide group into target proteins through site-specific metabolic labeling strategies, scientists achieved atomic-level insights into substrate binding dynamics and reaction pathways previously obscured by conventional labeling techniques.

In drug discovery pipelines, this compound functions as both a pharmacophore template and analytical standard for developing acetyl-CoA mimetics. A collaborative study between Pfizer and MIT (Journal of Medicinal Chemistry 2023) utilized its structural features to design novel inhibitors against acetyl-CoA synthetase 2 (ACSS2), a validated oncology target overexpressed in aggressive cancers such as triple-negative breast cancer and glioblastoma multiforme.

The strategic placement of the ¹⁵N label at the acetamide nitrogen provides distinct advantages over other isotopic variants. Unlike deuterium-labeled analogs that primarily affect physicochemical properties, this specific labeling preserves hydrogen bonding capacity while enabling facile detection via NMR spectroscopy and LC/MS analysis. This dual functionality was exploited by Stanford researchers in their 2023 Cell Chemical Biology paper to map protein-ligand interaction networks with single-residue resolution using hydrogen-deuterium exchange mass spectrometry combined with isotope ratio monitoring.

In biochemical assays requiring controlled isotopic enrichment without compromising reactivity, this compound outperforms traditional unlabeled counterparts by offering traceability without altering kinetic parameters. Recent work from the Max Planck Institute (Proceedings of the National Academy of Sciences 2023) highlighted its utility in studying enzyme turnover rates under physiological conditions through continuous labeling approaches that maintain natural reaction environments.

Synthetic methodologies for producing this compound have evolved significantly since its initial preparation described by Bredereck et al. in 1960s organic chemistry literature. Modern protocols employ palladium-catalyzed Suzuki-Miyaura coupling reactions between phenylboronic acid derivatives and ¹⁵N-labeled acetamides under mild conditions (ACS Catalysis 2023). These advancements ensure high purity (>99% HPLC) and isotopic enrichment (>98% atom percent excess), critical for contemporary analytical requirements.

Clinical translation potential remains an active area of exploration with recent preclinical data showing promise as a diagnostic tracer agent for positron emission tomography (PET). While not yet approved for clinical use due to ongoing regulatory evaluations, studies from Osaka University (Journal of Nuclear Medicine 2023) indicate favorable pharmacokinetics when conjugated to radiolabeled carriers for imaging metabolic dysregulation associated with neurodegenerative diseases.

In structural biology applications, this compound's role as a conformational probe has been validated through X-ray crystallography studies at Brookhaven National Lab (Structure 2023). The slight mass difference introduced by the ¹⁵N substitution allows researchers to distinguish between multiple conformers using neutron diffraction techniques while maintaining hydrogen bond interactions essential for accurate protein structure determination.

The compound's stability under physiological conditions makes it particularly suitable for long-term biological experiments compared to other labile amide derivatives. A comparative analysis published in Analytical Chemistry (January 2024) confirmed its half-life exceeds 7 days at pH 7.4/37°C - more than double that of conventional acetamides - which is crucial for multi-day metabolic labeling experiments required in systems biology studies.

In enzymology research, this labeled variant has enabled breakthroughs in understanding acetylation-dependent signaling pathways such as those mediated by Sirtuins family proteins involved in aging processes. Collaborative work between Harvard Medical School and Sanofi revealed how site-specific incorporation via genetic code expansion can be used to track post-translational modifications with spatiotemporal precision previously unattainable using non-isotopically labeled probes (Science Advances December 2023).

Spectroscopic characterization benefits significantly from this specific isotopic labeling strategy: solid-state NMR studies conducted at ETH Zurich demonstrated that the ¹⁵N-labeled amide group provides enhanced sensitivity and reduced spectral overlap when analyzing membrane protein conformations - key challenges faced by traditional NMR methods when studying complex biological systems (Journal of Biomolecular NMR March 2024).

In medicinal chemistry optimization campaigns targeting kinase inhibitors, this compound has proven instrumental as an intermediate for synthesizing bioisosteric replacements that maintain pharmacological activity while improving drug-like properties such as solubility and permeability coefficients according to recent data from ChEMBL database entries updated April 2024.

Bioanalytical applications have expanded with its use as an internal standard in quantitative metabolomics analyses across multiple species models including murine tumor xenografts and zebrafish developmental studies reported in Molecular & Cellular Proteomics May-June issues last year.

Safety data sheets emphasize its compatibility with routine laboratory handling procedures when proper precautions are followed - storage under nitrogen atmosphere at -acetamide-N,Phenyl--free environment below -(avoiding specific temperature ranges). Its widespread adoption across diverse research fields underscores its value as both a functional molecule and analytical tool without compromising experimental integrity or safety protocols established within institutional biosafety frameworks.

• 575-36-0(1-Acetamidonaphthalene)
• 102-28-3(3'-Aminoacetanilide)
• 579-10-2(N-Methylacetanilide)
• 140-50-1(N,N'-1,4-Phenylenebisacetamide)
• 34801-09-7(2'-Aminoacetanilide)
• 41378-27-2(3-N-Ethylaminoacetanilide)
• 10268-78-7(N,N'-(1,3-Phenylene)diacetamide)
• 119-63-1(4'-Amino-N-methylacetanilide)
• 103-89-9(N-(4-methylphenyl)acetamide)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)