N-in-Boc-D-tryptophan is a protected amino acid derivative in which the indole-containing side chain of tryptophan is attached to a D-configured α-amino acid backbone, with the α-amino group masked as a Boc (tert-butoxycarbonyl) carbamate. The molecule bears a free carboxylic acid functional group while the Boc protecting group controls chemoselectivity by preventing unprotected amine participation in coupling or side reactions during stepwise synthesis. It is used as a precursor for peptide and peptide-mimetic assembly, where the protected α-amino functionality supports controlled formation of amide bonds and the indole side chain provides a heteroaromatic handle for subsequent derivatization or structure-activity studies.
CAT No: CP02023
CAS No:201290-11-1
Synonyms/Alias:201290-11-1;(R)-2-Amino-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)propanoicacid;H-D-Trp(Boc)-OH;N-in-Boc-D-tryptophan;H-D-TRP-OH;CTK8B7672;MolPort-020-004-700;ANW-58119;ZINC34369792;1-(tert-Butoxycarbonyl)-D-tryptophan;AJ-88195;AK-87743;RT-023598;B-7723
N-in-Boc-D-tryptophan is a D-configured tryptophan derivative in which the indole-containing side chain remains unmodified while the amino group is protected as a Boc carbamate and the carboxyl functionality is present for peptide-grade coupling chemistry. The stereogenic center at the alpha-carbon fixes the D-configuration, enabling enantiopure incorporation into peptide sequences and stereochemically defined analogs. The Boc group provides acid-labile protection for the N-terminus during synthesis, while the indole ring supports electrophilic substitution and can participate in noncovalent interactions such as π-stacking in molecular recognition studies. The compound's protected amine and chiral amino acid framework make it a practical chiral intermediate for protected amino acid synthesis, peptide building block preparation, and downstream functionalization of the tryptophan side chain.
1. Peptide Synthesis
N-in-Boc-D-tryptophan is used in peptide synthesis workflows where a D-tryptophan residue must be introduced with controlled N-protection. The Boc-protected amino group supports standard peptide coupling strategies after activation of the carboxyl group, while the indole side chain tolerates many coupling and purification conditions without requiring immediate side-chain protection. Boc deprotection can be applied selectively to generate a reactive amine for iterative chain elongation, enabling compatibility with stepwise solid-phase or solution-phase assembly of D-amino acid peptides. The resulting D-tryptophan-containing peptides can be used to probe stereochemical effects on folding, stability, and binding interactions in peptide science and chemical biology.
2. Peptidomimetics And SAR
N-in-Boc-D-tryptophan is applied in peptidomimetic and structure-activity relationship studies that require precise stereochemical placement of an indole-bearing residue. The D-configuration at the alpha-carbon and the intact indole ring allow systematic variation of spatial orientation and aromatic pharmacophore presentation within peptide analog scaffolds. Boc protection supports sequential synthesis of analog libraries, while indole reactivity can be leveraged for later derivatization steps such as electrophilic substitution or conjugation handles installation. The synthesized D-tryptophan analogs can serve as defined fragments for SAR mapping and molecular design efforts in drug discovery chemistry.
3. Side-Chain Functionalization
N-in-Boc-D-tryptophan is suitable for side-chain functionalization routes that exploit the indole's aromatic reactivity while maintaining orthogonal protection at the amino terminus. The Boc carbamate protects the alpha-amine during indole-directed transformations, helping prevent undesired amide or urea formation during electrophilic or oxidative functionalization chemistry. The indole can be converted into substituted derivatives that introduce functional groups for downstream conjugation, affinity labeling, or incorporation into larger molecular assemblies. The resulting functionalized D-tryptophan intermediates can be carried forward into labeled probes, receptor-binding motifs, or synthetic intermediates for complex molecule construction.
4. Chemical Biology Bioconjugation
N-in-Boc-D-tryptophan is used in chemical biology and bioconjugation programs where a chiral, indole-containing amino acid building block is required for defined labeling chemistry. The protected amine and carboxyl functionality support controlled incorporation into peptide linkers, and Boc deprotection can generate a coupling-ready amine for attachment to carriers, scaffolds, or affinity reagents. The indole ring can participate in noncovalent interactions that influence conjugate binding behavior, while its chemical reactivity can enable installation of conjugation motifs depending on the chosen derivatization strategy. D-tryptophan-containing conjugates prepared from this intermediate can be used to study biomolecular recognition, probe stability, and stereochemical effects in labeling and assay development.
5. Pharmaceutical Manufacturing Intermediates
N-in-Boc-D-tryptophan is relevant to pharmaceutical manufacturing and fine chemical synthesis as a chiral amino acid intermediate for producing D-tryptophan-containing drug candidates or process intermediates. The Boc-protected N-terminus provides a robust handle for protecting-group management during multi-step synthesis, while the indole side chain supports incorporation into peptide-like structures and heteroaromatic-containing intermediates. The defined stereochemistry at the alpha-carbon supports consistent downstream quality for stereochemically specified active pharmaceutical ingredient (API) intermediates and related process streams. The compound's role as a protected amino acid derivative makes it compatible with scalable synthetic planning where orthogonal protection and predictable coupling behavior are required for manufacturing route design.
6. Analytical Research Standards
N-in-Boc-D-tryptophan is applied in analytical research for generating stereochemically defined standards and reference materials used in method development and impurity profiling. The D-configuration and Boc-protected amino group provide a stable chemical identity that can be tracked by chromatographic and spectrometric techniques, supporting differentiation from L-tryptophan analogs and other protecting-group variants. The indole chromophore contributes to detectability in UV-based methods, while the protected functional groups can aid in constructing calibration sets for amino acid derivative quantitation. The compound can also serve as a starting point for preparing related standards and internal references used to verify peptide coupling outcomes and stereochemical integrity during analytical characterization.
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