Ac-Phe-NHMe is an N-acetylated phenylalanine amide derivative in which the phenylalanine α-amino group is converted to an acetamide (Ac-NH-) and the C-terminal carboxyl functionality is present as a methyl amide (-NHMe), yielding a peptide-like, non-free amino acid structure with a benzyl side chain. The molecule contains an aromatic side chain characteristic of phenylalanine, while the α-carboxyl group is masked as an amide and the α-amino group is protected as an acetamide, leaving no free amino or carboxyl groups for direct coupling. Ac-Phe-NHMe is used as a defined amino-acid amide building block or reference substrate in peptide chemistry, such as for preparing related amide-linked fragments, studying amide bond formation or cleavage in solution, or supporting analytical method development for phenylalanine-containing peptide motifs.
CAT No: CP26508
CAS No:17186-60-6
Synonyms/Alias:17186-60-6;Ac-Phe-NHMe;SCHEMBL13956933;CTK8F7543;Acetyl-L-phenylalaninemethylamide;ZINC2560838;AKOS022181253;AJ-40661;AK-60146;(S)-2-Acetamido-N-methyl-3-phenylpropanamide
Ac-Phe-NHMe is an N-acetylated phenylalaninamide derivative in which the carboxyl group is converted to an acetamide (Ac-) and the C-terminus is capped as a methylamide (-NHMe). This neutral, peptide-like building block preserves the phenylalanine side chain for hydrophobic and aromatic interaction studies while providing a defined, non-ionizable end-group pattern that is commonly used to model short peptide motifs in chemical biology and peptide chemistry workflows. Researchers use this compact substrate format to investigate sequence-dependent recognition, optimize peptide-like ligands, and generate well-defined standards for analytical characterization of amide-containing fragments.
1. Peptide Motif Modeling
Ac-Phe-NHMe is frequently used as a short, defined peptide-mimetic fragment to model the local physicochemical behavior of phenylalanine-containing motifs without introducing terminal charges that can complicate interpretation. Chemical biology and peptide research groups employ this type of capped amino acid amide to probe aromatic side-chain contributions in binding or recognition assays, to benchmark fragment behavior in solvent and aggregation studies, and to support structure-property analyses during peptidomimetic development. Because both termini are protected as amide caps, the compound offers a stable, reproducible reference fragment for comparing how phenylalanine substitutions affect downstream assay readouts.
2. Enzyme Substrate Studies
Ac-Phe-NHMe is also used as a defined amide-containing substrate or fragment in enzyme and protease research where the goal is to evaluate how an aromatic residue environment is processed in a controlled, minimal context. Protein chemistry laboratories and assay developers use capped phenylalanine amide derivatives to reduce ambiguity from variable end-group chemistry and to generate consistent kinetic or endpoint measurements when screening catalytic activity or inhibitor effects against peptide-like targets. The methylamide C-terminus provides a convenient, non-extendable endpoint that helps isolate the contribution of the phenylalanine side chain and the local amide pattern.
3. Analytical Fragment Standards
Ac-Phe-NHMe serves as a practical analytical standard for LC-MS and related characterization workflows that require reference material for phenylalanine-containing amide fragments. Analytical chemistry teams use this compound to confirm retention behavior, support method qualification for peptide fragment detection, and enable calibration or identity checks when monitoring degradation, synthesis, or enzymatic turnover products. The well-defined, capped structure reduces variability associated with free amino acids or ionizable termini, improving reproducibility when building internal reference sets for peptide chemistry and protein-chemistry studies.
4. Peptidomimetic Intermediate Building Block
Ac-Phe-NHMe is commonly incorporated as a building block in the preparation of larger peptide-like structures where a phenylalanine residue is required in a capped amide form. Medicinal chemistry and process development groups use such fragments to assemble defined amide linkages during the synthesis of peptidomimetics, to create reference compounds for SAR (structure-activity relationship) studies, or to generate fragment libraries for downstream coupling strategies. The presence of the N-acetyl and C-methylamide caps provides a controlled end-group identity that can be important for maintaining consistent fragment behavior across synthesis batches and analytical comparisons.
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