Ac-L-Trp-OMe is an N-acetylated, L-tryptophan methyl ester amino acid derivative in which the indole-containing side chain of tryptophan is retained while the amino terminus is capped as an acetamide and the carboxyl group is esterified as a methyl ester. The molecule bears an indole aromatic system on the side chain and contains an acetamide carbonyl plus a methyl ester carbonyl, with the stereochemistry at the α-carbon specified as L. Ac-L-Trp-OMe is used as a protected/functionalized building block for peptide and amide bond formation in solution-phase or solid-phase synthesis workflows and as a substrate-like reagent in analytical or structure-reactivity studies where masking of the free amino and carboxyl groups is required.
CAT No: CP25704
CAS No:2824-57-9
Synonyms/Alias:MethylN-acetyl-L-tryptophanate;2824-57-9;AC-TRP-OME;Methylacetyltryptophanate;L-Tryptophan,N-acetyl-,methylester;UNII-MUP4Y18ZQ5;N-Acetyltryptophanmethylester;methyl(2S)-2-acetamido-3-(1H-indol-3-yl)propanoate;AmbotzAAA1943;AC1L2SM1;AC1Q41IM;Acetyltryptophanmethylester;MUP4Y18ZQ5;SCHEMBL468840;MethylL-N-acetyltryptophanate;CHEMBL1276128;CTK4G1077;MolPort-003-911-054;XZECNVJPYDPBAM-ZDUSSCGKSA-N;ZINC107108;N-Acetyl-L-tryptophanmethylester;ANW-60736;AR-1J3450;ZINC00107108;AJ-11254
Chemical Name:N-alpha-Acetyl-L-tryptophane methyl ester
Ac-L-Trp-OMe is an N-acetylated L-tryptophan methyl ester designed to serve as a protected, esterified indole-containing amino acid building block for peptide and amide assembly workflows. The indole side chain of tryptophan provides a chemically distinctive aromatic functionality, while the methyl ester and N-acetyl group suppress free carboxyl and amine reactivity, respectively, enabling controlled downstream coupling or transformation. In research and development settings, this form is commonly selected when a tryptophan residue must be introduced with minimal side reactions and with a defined terminal functional group for subsequent synthetic steps.
1. Peptide Fragment Coupling
Ac-L-Trp-OMe is used in peptide synthesis as a tryptophan-containing fragment where the N-acetyl group and methyl ester protect terminal functionality during segment assembly. Custom peptide synthesis groups and medicinal chemistry teams often rely on this type of protected amino acid derivative to prepare defined peptide intermediates that can be carried forward into amide bond formation at the next stage, including the construction of tryptophan-rich sequences used for structure-activity relationship studies. The indole side chain remains available for later derivatization or for maintaining aromatic character in the target peptide or peptidomimetic scaffold.
2. Amide-Linked Intermediate Preparation
Ac-L-Trp-OMe is frequently employed to generate well-defined acylated tryptophan intermediates for solution-phase or convergent synthesis strategies, particularly when controlling the reactivity of the terminal groups is important for reproducible coupling. Pharmaceutical intermediate developers use this derivative to build stepwise toward larger amide-containing molecules, including protected peptide fragments and tryptophan-containing peptidomimetics, where terminal group masking helps reduce undesired oligomerization or side reactions. The methyl ester functionality supports downstream conversion to other carboxyl-activated forms or controlled transformations depending on the chosen synthetic route.
3. Indole-Functional Derivatization Studies
Ac-L-Trp-OMe is also used in chemical biology and medicinal chemistry research where the tryptophan indole motif is intentionally retained for subsequent functionalization, labeling, or incorporation into aromatic interaction studies. Because the indole is a key structural element in many bioactive peptide-like scaffolds, maintaining it in a protected amino acid derivative format helps researchers prepare intermediates for indole-directed chemistry while keeping terminal amine and carboxyl reactivity suppressed. This makes Ac-L-Trp-OMe a practical starting material for developing tryptophan-bearing analogs used in binding studies, conformational probing, and SAR-focused library synthesis.
4. Analytical Reference Material Development
Ac-L-Trp-OMe can serve as a defined tryptophan-containing reference compound in analytical method development and characterization workflows for peptide intermediates and related derivatives. Analytical chemistry teams use methyl ester and N-acetylated forms to establish retention behavior and fragmentation patterns for tryptophan-containing species in LC-MS workflows, supporting identification and confirmation of synthetic intermediates during process development. In peptide and intermediate manufacturing research, having a stable, well-characterized derivative like Ac-L-Trp-OMe helps streamline verification of tryptophan-containing building blocks and their downstream conversion products.
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