Fmoc-N-Me-Trp-OH is an Fmoc-protected amino acid derivative based on tryptophan bearing an N-methylated amide nitrogen (N-Me) and a free carboxylic acid, classifying it as a protected, non-native tryptophan analogue for peptide-related synthesis. The molecule contains the indole side chain of tryptophan, an N-methyl substituent that reduces the amino nitrogen's hydrogen-bonding and changes acylation behavior, and an Fmoc group that masks the amino functionality while leaving the carboxyl group available for coupling. In synthesis workflows such as stepwise solid-phase or solution-phase assembly of peptides, this protected building block is used to introduce N-methyl tryptophan residues and to support controlled chemoselectivity during sequential bond formation.
CAT No: CP26201
CAS No:112913-63-0
Synonyms/Alias:112913-63-0;Fmoc-MeTrp-OH;Fmoc-Nalpha-methyl-L-tryptophan;Fmoc-N-Me-Trp-OH;Na-Fmoc-Na-methyl-L-tryptophan;(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-(1H-indol-3-yl)propanoic acid;(s)-2-((((9h-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(1h-indol-3-yl)propanoic acid;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino}-3-(1H-indol-3-yl)propanoic acid;N-Fmoc-N-methyl-L-tryptophan;SCHEMBL3726968;L-Tryptophan, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-;Na-(((9H-fluoren-9-yl)methoxy)carbonyl)-Na-methyl-L-tryptophan;MFCD02682369;AKOS015837151;AS-83800;DB-234856;CS-0091374;D75117;L-Tryptophan,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-;
Fmoc-N-Me-Trp-OH is a chiral tryptophan-derived amino acid bearing an N-methylated amide nitrogen and a free carboxylic acid, with the indole side chain preserved for aromatic and heteroaromatic reactivity. The Fmoc group on the alpha-amino function provides a base-stable, peptide-synthesis-compatible protecting strategy, while N-methylation modulates amide acidity and peptide backbone conformational preferences during coupling and subsequent transformations. The molecule therefore functions as a protected, stereodefined amino acid building block in which the indole ring can participate in electrophilic substitution, oxidative chemistry, or orthogonal derivatization depending on conditions. The combination of Fmoc protection, an N-methylated backbone, and an unprotected side-chain indole makes it suitable as a chiral intermediate for peptide construction and as a downstream precursor for tryptophan-containing analogs used in biochemical and materials-oriented research.
1. Peptide Synthesis
Fmoc-N-Me-Trp-OH is applied in solid-phase peptide synthesis and related protected amino acid chemistry where the Fmoc carbamate enables controlled N-deprotection and iterative chain elongation. The alpha-carboxylic acid and Fmoc-protected, N-methylated amino functionality support standard peptide coupling logic while the N-methyl group can influence backbone hydrogen-bonding patterns and local conformational bias in the assembled sequence. The indole side chain remains available for incorporation into tryptophan-rich motifs without requiring side-chain protection for many coupling workflows, supporting downstream peptide analog generation. The resulting N-methylated tryptophan residues can be used to build peptide libraries, probe sequence-dependent folding, and generate chemically defined peptide standards for analytical and structure-function studies, aligning amino acid derivatization with peptide science needs.
2. Peptidomimetics And SAR Studies
Fmoc-N-Me-Trp-OH is used in peptidomimetic construction and structure-activity relationship studies where N-methylation of the tryptophan backbone provides a handle for tuning amide polarity and conformational behavior. The protected amino acid architecture allows incorporation of an N-methyl indole-containing residue into peptide-like scaffolds while maintaining compatibility with fragment assembly strategies that rely on protected amino acid intermediates. The indole ring can serve as a pharmacophore element for aromatic recognition and can be further modified to generate analogs for SAR mapping, including derivatives that alter electronic density or steric profile at the indole. The compound's stereodefined alpha center and protected amine functionality support systematic library synthesis and iterative analog preparation in medicinal chemistry and chemical biology programs focused on molecular recognition and binding-site interrogation.
3. Chemical Biology Labeling
Fmoc-N-Me-Trp-OH can be employed in chemical biology research to introduce indole-bearing, N-methylated tryptophan units into peptide probes and biomolecule conjugates. The preserved indole functionality enables selective derivatization routes such as electrophilic substitution or oxidative transformations under conditions that can be coordinated with orthogonal protecting-group strategies used for peptide fragments. The Fmoc-protected amino acid format supports building well-defined peptide handles that can subsequently be functionalized for tagging, affinity capture, or imaging reagent preparation. The resulting labeled or derivatized tryptophan-containing constructs can be used as molecular tools to study binding interactions, substrate recognition, or localization effects in biochemical assays, leveraging amino acid chemistry to create chemically addressable biomolecular probes.
4. Process Chemistry Intermediate
Fmoc-N-Me-Trp-OH is suitable for process chemistry intermediate preparation in fine chemical synthesis where protected amino acid handling, storage stability, and controlled deprotection are central to manufacturing workflows. The Fmoc group provides a robust protection strategy under many coupling and purification conditions, while the free carboxylic acid supports downstream conversion to activated esters or coupling reagents as part of scalable peptide-building operations. N-methylation of the alpha-amino nitrogen can reduce susceptibility to certain side reactions associated with unmodified amines, supporting reproducible incorporation of N-methylated residues into larger peptide intermediates. The indole side chain offers a predictable aromatic functionality for later derivatization steps when orthogonal protection and selective transformation planning are required, enabling reliable route design for tryptophan-containing intermediate production.
5. Analytical Standards and Method Development
Fmoc-N-Me-Trp-OH is used in analytical research and method development as a chemically defined reference material for monitoring protected amino acid incorporation, peptide coupling efficiency, and deprotection outcomes. The distinct combination of Fmoc chromophore, N-methylated backbone character, and indole aromaticity provides identifiable signals in common analytical platforms such as LC-MS and UV-based detection schemes. The free carboxylic acid and Fmoc-protected amine allow preparation of calibration standards, fragment standards, or peptide-derived benchmarks used to interpret reaction progress and characterize final products. The compound's stereochemical integrity and protected-group signature make it compatible with QA/QC-oriented characterization workflows in peptide science, supporting accurate structural verification and impurity tracking during amino acid derivative and peptide manufacturing development.
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