5-Hydroxy-D-tryptophan is a non-proteinogenic tryptophan derivative featuring an indole ring bearing a 5-hydroxy substituent and a stereochemically specified D-configuration at the α-carbon. The molecule contains both an α-amino group and a carboxyl group, while the indole system provides aromatic character and the 5-hydroxy substituent introduces a phenolic functionality that can participate in hydrogen bonding and acid-base behavior. As a labeled amino acid analogue for structure-function and chemical biology studies, it is used in peptide-related synthesis and analytical method development to introduce a hydroxylated indole side chain and to support studies of how altered aromatic/phenolic properties affect peptide conformation and reactivity.
CAT No: CP24702
5-Hydroxy-D-tryptophan is a D-configured tryptophan analog featuring a phenolic 5-hydroxy substituent on the indole ring, providing an additional site for derivatization and analytical discrimination relative to standard tryptophan. This aromatic hydroxyl group enables downstream chemical modification and supports its use as a defined amino acid reference in chemical biology and analytical workflows. Researchers also rely on its stereochemical identity when preparing standards or constructing defined peptide/peptidomimetic segments where D-amino acid incorporation is required.
1. Peptidomimetic Building Blocks
5-Hydroxy-D-tryptophan is used as a D-amino acid building block for assembling defined peptide and peptidomimetic structures in solution-phase or solid-phase synthesis workflows. The indole-phenol functionality provides a chemically addressable handle for post-synthetic modification strategies, allowing researchers to tune aromatic reactivity, introduce additional functional groups, or generate site-specific analogs for structure-activity relationship studies. Medicinal chemistry and peptide chemistry groups commonly select this residue when they need a stereochemically defined tryptophan analog with an extra hydroxyl-bearing aromatic motif rather than relying on standard L-tryptophan.
2. Chemical Biology Reference Standards
5-Hydroxy-D-tryptophan serves as a chemically defined reference material for chemical biology experiments that track tryptophan-related motifs or quantify incorporation of aromatic amino acid analogs in synthetic or semi-synthetic systems. The D-configuration and 5-hydroxy substitution help distinguish it from endogenous tryptophan species during analytical readouts, supporting studies that require unambiguous identification of an analog residue in complex mixtures. Analytical method developers and research laboratories use it to validate derivatization-based workflows and to benchmark LC-MS or related detection strategies that resolve indole-containing amino acids.
3. LC-MS Quantification Support
5-Hydroxy-D-tryptophan is widely used in quantitative analytical method development as an external calibration or reference compound for indole/phenolic amino acid species. The distinct mass and aromatic hydroxyl functionality support robust chromatographic separation and targeted detection in LC-MS workflows aimed at measuring amino acid analogs, degradation products, or labeled/unlabeled mixtures containing tryptophan-derived motifs. This makes it a practical choice for laboratories performing routine characterization of synthetic intermediates, peptide fragments, or analytical standards where a stereochemically defined, 5-hydroxy-substituted indole amino acid is required.
4. Aromatic Derivatization Studies
5-Hydroxy-D-tryptophan is used as a substrate analog for derivatization and reactivity studies targeting indole phenolic chemistry. The 5-hydroxy group enables controlled functional group transformations that can be used to generate defined derivatives for downstream detection, immobilization, or comparative reactivity experiments. Chemical biology and materials-oriented research groups often select this compound when they want a tryptophan-based aromatic scaffold bearing a hydroxyl handle, while also maintaining D-stereochemical identity to ensure consistent behavior in stereospecific analytical or synthetic contexts.
1. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
4. Emerging applications of nanotechnology for diagnosis and therapy of disease: a review
5. Myotropic activity of allatostatins in tenebrionid beetles
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More