Ac-Met-alpha-naphthyl ester is an amino acid ester derivative of methionine in which the carboxyl group is converted to an alpha-naphthyl ester and the amino functionality is acetylated (Ac-), yielding a protected, non-zwitterionic form. The molecule contains a thioether side chain characteristic of methionine, while the ester linkage and N-acetyl group modulate polarity and chemoselectivity by masking the free amino and carboxyl groups. In peptide chemistry and chemical biology workflows, this ester form can function as a substrate-like building block or as a labeled/aryl-ester reagent for analytical method development, derivatization strategies, and the preparation of more complex methionine-containing intermediates.
CAT No: CP27373
CAS No:69975-69-5
Synonyms/Alias:69975-69-5;L-Methionine,N-acetyl-,1-naphthalenylester;naphthalen-1-yl(2S)-2-acetamido-4-(methylsulfanyl)butanoate;AC1L2P8N;Ac-Met-alpha-naphthylester;CTK7B5623;AC-MET-ALPHA-NAPHTHYLESTER;Ac-Methionine-alpha-naphthylester;ZINC2572076;AR-1J3344;N-Acetylmethioninealpha-naphthylester;AM001493;AM031166;ACETYL-L-METHIONINE1NAPHTHYLESTER;N-Acetyl-L-methioninealpha-naphthylester;3B3-056911;naphthalen-1-yl(2S)-2-acetamido-4-methylsulfanylbutanoate
Ac-Met-alpha-naphthyl ester is an acetyl-protected methionine derivative in which the amino acid carboxyl group is esterified with alpha-naphthol, providing a hydrophobic aromatic handle alongside the sulfur-containing methionine side chain. This structure is commonly used as a chemically defined substrate or building block in peptide/amide bond formation studies and in analytical or materials-related assays where controlled reactivity and a stable, ester-linked aromatic moiety are advantageous. The acetylated amino functionality reduces undesired side reactions, making the reagent practical for downstream derivatization and method development workflows that require a consistent methionine-containing motif.
1. Peptide Coupling Substrate
Ac-Met-alpha-naphthyl ester is used in peptide chemistry workflows as a methionine-containing, acetylated amino acid ester building block for evaluating coupling conditions and optimizing segment condensation or derivatization steps. Researchers in custom peptide synthesis and peptide process development often select this type of protected methionine ester when they want a defined, non-zwitterionic reagent that minimizes complications from free amino or carboxyl groups. The alpha-naphthyl ester functionality also supports monitoring or downstream tagging strategies in reaction screening contexts where an aromatic group improves handling and detectability.
2. Analytical Derivatization Reagent
Ac-Met-alpha-naphthyl ester is applied as a derivatization reagent for analytical method development that benefits from introducing a strongly absorbing aromatic moiety. Analytical chemistry groups use this reagent to generate methionine-related derivatives that can be separated and detected by common chromatographic systems, supporting assay development for reaction monitoring, impurity profiling, or substrate conversion studies. The acetyl protection and ester linkage help produce reproducible derivatives rather than heterogeneous mixtures that can arise from partially functionalized methionine materials.
3. Enzyme Assay Development
Ac-Met-alpha-naphthyl ester is frequently used in biochemical and chemical biology assay development as a defined methionine ester substrate for studying ester-cleaving activity or related enzymatic transformations under controlled in vitro conditions. Because the reagent contains a methionine side chain with a sulfur-containing thioether and an aromatic ester component, it can be incorporated into experimental designs where release or conversion of the naphthyl ester provides a measurable readout. This makes it useful for researchers developing substrate panels, screening conditions, or comparative studies of catalytic activity using chemically consistent inputs.
4. Pharmaceutical Intermediate Building Block
Ac-Met-alpha-naphthyl ester is also used as a pharmaceutical intermediate building block in synthetic development where a methionine-derived motif with an acetylated amino group and an activated ester handle is required for further functional group manipulation. Process chemistry teams and medicinal chemistry groups may employ this reagent to access methionine-based intermediates that can be carried forward into larger coupling sequences, protecting-group strategies, or derivatization steps toward target scaffolds. The aromatic alpha-naphthyl ester provides a convenient, stable intermediate form that can be transformed selectively in downstream synthetic planning.
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