Ac-DL-Phe-beta-naphthyl ester is an amino acid ester derived from the racemic (DL) form of phenylalanine, featuring an N-acetylated amino functionality and a carboxyl group converted to a beta-naphthyl ester. The molecule contains an acetamide (Ac-NH-) on the alpha-amino position, an ester linkage to the beta-naphthol moiety, and a benzyl-like aromatic side chain characteristic of phenylalanine, with stereochemistry expressed as a DL mixture rather than a single enantiomer. As an activated amino acid ester, it is used as a substrate or building block in peptide-related synthesis and analytical method development where controlled reactivity of the ester and the aromatic naphthyl group can support derivatization, labeling, or monitoring of coupling steps.
CAT No: CP26763
CAS No:20874-31-1
Synonyms/Alias:APNE;20874-31-1;N-Acetyl-DL-phenylalaninebeta-naphthylester;l66jcovy1r&mv1;N-Acetylphenylalaninebeta-naphthylester;MLS002694779;N-Acetyl-dl-phenylalanine2-naphthylester;CHEBI:7219;naphthalen-2-ylN-acetylphenylalaninate;ST50828199;Phenylalanine,N-acetyl-,2-naphthalenylester;naphthalen-2-yl2-acetamido-3-phenylpropanoate;AC1L3ZXW;NCIOpen2_009434;A7512_SIGMA;AC1Q5L19;SCHEMBL1569237;CHEMBL1900052;CTK4E5360;BBXRRTJNJCPGBU-UHFFFAOYSA-N;MolPort-002-501-578;HMS3085B07;NSC87855;AC-DL-PHE-BETA-NAPHTHYLESTER;beta-naphthylN-acetylphenylalaninate
Ac-DL-Phe-beta-naphthyl ester is an acetylated, racemic phenylalanine beta-naphthyl ester derivative designed for chemical biology and enzyme-assay development where an aromatic, leaving-group ester is advantageous for monitoring ester cleavage or substrate turnover. Its DL stereochemical mixture and N-acetylated amino terminus make it a stable, non-proteinogenic substrate format for in vitro studies, while the beta-naphthyl ester functionality provides a convenient chromophore/fluorophore-compatible readout pathway in many assay designs.
1. Enzyme Substrate Assays
Ac-DL-Phe-beta-naphthyl ester is used as a defined small-molecule substrate in vitro to evaluate esterase or protease-related activities that accept amino-acid ester motifs. Researchers in enzymology and biochemical assay development typically select this format to ensure a consistent aromatic leaving group, enabling straightforward monitoring of reaction progress in screening workflows and method optimization. The N-acetylated amino terminus and esterified carboxylate reduce ambiguity from free amino acid reactivity, supporting reproducible substrate handling across plates and time-course experiments.
2. Chromogenic/Fluorogenic Readout Development
Ac-DL-Phe-beta-naphthyl ester is commonly incorporated into analytical assay systems that rely on beta-naphthol-type product formation for signal generation. Analytical chemists and chemical biology groups use this derivative when they want an aromatic ester that can translate enzymatic cleavage into a measurable spectroscopic or fluorescence response, facilitating kinetic measurements and comparative studies of substrate specificity. The beta-naphthyl ester group is the key structural feature enabling downstream detection without requiring additional derivatization steps in many established assay formats.
3. Racemate-Compatible Screening Reagents
Ac-DL-Phe-beta-naphthyl ester is frequently selected for exploratory screening where stereochemical purity is not required, such as early-stage substrate profiling or inhibitor/condition optimization. Because the material is supplied as a DL mixture, it supports robust, high-throughput comparisons of relative activity trends without the added cost and handling complexity of single-enantiomer substrates. This makes it practical for industrial and academic process-development contexts where assay throughput and reproducibility are prioritized over enantioselective interpretation.
4. Pharmaceutical Intermediate R&D
Ac-DL-Phe-beta-naphthyl ester is also used as a research-grade intermediate substrate in medicinal chemistry and pharmaceutical process R&D settings that require well-characterized amino-acid-derived ester functionality for method development. Teams developing ester-related analytical methods, reaction monitoring protocols, or substrate-based qualification tests may use this compound as a reference material because it combines a protected amino terminus (acetylated) with an aromatic ester handle. The acetylated, esterified structure provides a controlled chemical form that can be used to validate analytical workflows and reaction endpoints during derivative synthesis campaigns.
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