Ac-Trp-NHMe is an N-acetylated tryptophan amide derivative in which the tryptophan side chain (indole) is retained while the α-amino group is acylated and the carboxyl group is converted to a methylamide, yielding a peptide-like, non-zwitterionic structure. The molecule contains an acetyl (Ac) group on nitrogen, an indole aromatic system on the side chain, and a terminal methylamide (-NHMe) functionality, with stereochemistry not specified in the name. Ac-Trp-NHMe is used as a defined amino acid/peptide building block or reference substrate for peptide chemistry and analytical method development, including studies that require tryptophan-containing amide linkages or controlled reactivity relative to free amino acids.
CAT No: CP27311
CAS No:6367-17-5
Synonyms/Alias:AC-TYR-NHME;6367-14-2;Acetyl-L-tyrosinemethylamide;SCHEMBL12632559;CTK8F7547;ZINC2560842;6118AH
Ac-Trp-NHMe is an N-acetylated tryptophan amide featuring a tryptophan indole side chain and a C-terminal N-methylamide, forming a compact, peptide-like building block with reduced terminal reactivity. This structure is commonly used to model tryptophan-containing peptide motifs in chemical biology and peptide chemistry workflows where terminal groups are intentionally capped to control charge state and stability during downstream handling. Researchers leverage the indole functionality for studying tryptophan-specific behavior in peptide conformations, solvent effects, and analytical readouts, while the amide framework supports robust coupling into larger sequences or incorporation into reference materials.
1. Peptide Motif Building
Ac-Trp-NHMe is used as a tryptophan-containing peptide fragment for assembling short peptide sequences in solution-phase synthesis and for preparing defined tryptophan motifs used in structure-property studies. The N-acetyl and C-terminal N-methylamide capping pattern helps minimize side reactions associated with free termini, making it practical for constructing peptide analogs that retain the indole side chain as the primary functional element. Chemical biology groups and peptide synthesis teams commonly select this capped tryptophan amide when they want a consistent, peptide-like local environment rather than a free amino acid.
2. Chemical Biology Reference Peptides
Ac-Trp-NHMe is frequently employed to generate reference compounds that isolate tryptophan contributions in assays and analytical experiments, including studies that monitor indole-related signals in peptide contexts. Because the molecule is already terminally protected as an amide, it is well suited for preparing standards for method development and for benchmarking peptide behavior under controlled conditions such as pH, solvent composition, or thermal handling. Researchers in peptide analytics and chemical biology use Ac-Trp-NHMe as a defined tryptophan-bearing control when comparing more complex peptide systems where terminal chemistry could otherwise confound interpretation.
3. Analytical Standard and LC-MS Calibration
Ac-Trp-NHMe supports quantitative and qualitative analytical workflows as a small, well-defined tryptophan peptide-like standard for LC-MS method development, retention-time scouting, and response verification for tryptophan-containing analytes. The acetylated N-terminus and N-methylamide C-terminus produce a reproducible fragmentation and chromatographic profile relative to free tryptophan or partially capped analogs, improving consistency when validating sample preparation and instrument performance. Analytical chemistry teams use this compound to ensure that tryptophan-containing peptide signals can be reliably tracked across runs, especially during optimization of peptide-focused separations.
4. Peptidomimetic and SAR Prototypes
Ac-Trp-NHMe is used as a starting fragment for peptidomimetic design and structure-activity relationship (SAR) prototype generation where tryptophan is incorporated as a key side-chain element while terminal groups are tuned for chemical stability and handling. Medicinal chemistry and peptide drug discovery groups often rely on capped tryptophan amide motifs to create series of analogs that differ in neighboring residues or backbone modifications, enabling clearer attribution of observed trends to structural changes. This compound's peptide-like amide connectivity makes it a practical intermediate for building larger analogs that preserve the indole-bearing pharmacophore context.
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