N-in-formyl-D-tryptophan hydrochloride is an N-formylated derivative of the amino acid tryptophan in the D stereochemical configuration, bearing an indole-containing aromatic side chain and a free carboxylic acid functionality. The molecule features an N-formyl amide at the amino terminus, a carboxyl group, and is present as a hydrochloride salt, which together modulate hydrogen-bonding and chemoselectivity by reducing the nucleophilicity of the amino group while maintaining an ionizable carboxyl. This compound is used as a chemically defined tryptophan building block for peptide- and amide-bond synthesis workflows and for analytical or labeling contexts where indole-bearing, N-protected amino acid substrates are required.
CAT No: CP02025
N-in-formyl-D-tryptophan hydrochloride is a D-configuration tryptophan derivative in which the amino group is converted to an N-formyl (formamide) functionality and the compound is provided as the hydrochloride salt, improving handling for peptide-coupling workflows. The indole side chain retains aromatic π-systems and can participate in electrophilic aromatic substitution, π-stacking interactions, and oxidative transformations typical of tryptophan chemistry. The carboxylic acid and N-formyl group create a protected amino acid framework that can be carried through coupling steps while maintaining stereochemical integrity at the α-carbon. The salt form modulates basicity and solubility, supporting downstream conversion into peptide building blocks, chiral intermediates, and analytical standards for amino acid derivatization studies.
1. Peptide Synthesis
N-in-formyl-D-tryptophan hydrochloride is applied in peptide synthesis as a chiral tryptophan building block where the N-formyl group functions as an amino-protecting strategy compatible with common peptide coupling conditions. The indole side chain remains chemically addressable for later functionalization, while the α-carboxyl group can be activated for amide bond formation to install D-tryptophan stereochemistry into growing sequences. Hydrochloride salt formation can aid in controlled handling and conversion to activated intermediates, supporting reproducible peptide assembly for research-grade and process-oriented workflows. Incorporation of D-tryptophan enables access to D-amino acid-containing peptides used in stability studies and stereochemical mapping of peptide recognition.
2. Chemical Biology Probes
N-in-formyl-D-tryptophan hydrochloride supports chemical biology research by providing a protected D-tryptophan scaffold that can be incorporated into peptide probes for studying receptor binding, protease selectivity, and stereochemical effects on molecular recognition. The indole moiety can serve as a functional handle for downstream conjugation or for spectroscopic readouts through indole-specific derivatization and oxidative chemistry, while the N-formyl protection helps maintain the amino functionality during probe construction. Hydrochloride salt behavior can facilitate formulation into coupling-ready solutions, enabling consistent probe synthesis for biochemical assays. The resulting D-tryptophan-containing probe derivatives can be used to interrogate binding-site preferences and to generate stereochemically defined peptide analogs for mechanistic studies.
3. Peptidomimetics And SAR
N-in-formyl-D-tryptophan hydrochloride is suitable for peptidomimetic and structure-activity relationship (SAR) studies where D-amino acid incorporation is used to tune conformational preferences and proteolytic stability in peptide-like scaffolds. The protected amino acid framework allows sequential assembly into analog series, with the indole side chain contributing aromatic interactions that often correlate with target affinity and selectivity. The N-formyl group can be managed through deprotection or conversion to alternative amine-protection states during synthetic route design, supporting iterative medicinal chemistry workflows. D-tryptophan analogs generated from this intermediate can be used to build SAR libraries that probe how stereochemistry and side-chain electronics influence binding and activity trends.
4. Analytical Derivatization Standards
N-in-formyl-D-tryptophan hydrochloride functions as an analytical reference material for amino acid derivatization, stereochemical verification, and method development in analytical chemistry. The combination of an indole side chain and an N-formyl protected amino group creates a defined chemical signature that can be tracked by chromatographic and spectrometric methods after conversion to appropriate derivatives. Hydrochloride salt form can improve reproducibility in sample preparation by stabilizing the protonation state during derivatization workflows. Stereochemically defined D-tryptophan standards derived from this compound can support quality control of peptide hydrolysates and verification of D-amino acid incorporation in synthetic materials.
5. Industrial Fine Chemical Synthesis
N-in-formyl-D-tryptophan hydrochloride is applicable to industrial fine chemical synthesis as a chiral amino acid intermediate for manufacturing D-tryptophan-containing peptide fragments and protected amino acid derivatives. The N-formyl protection strategy provides a controlled amino functionality that can be transformed into alternative protecting-group states or directly leveraged in coupling sequences, supporting scalable synthetic planning. The indole side chain is retained without altering stereochemistry, enabling downstream conversion into higher-value intermediates for peptide building blocks and specialty chemical production. Salt formation supports practical handling and can be integrated into process chemistry routes where consistent material transfer and defined protonation states are beneficial for reproducible intermediate generation.
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