2-Hydroxy-L-tryptophan is an L-tryptophan derivative bearing an additional hydroxyl substituent at the 2-position of the indole ring, making it a hydroxyindole amino acid within the tryptophan family. The molecule contains a free α-amino group and a free carboxyl group alongside the indole nitrogen and the phenolic hydroxyl, and its side chain retains the aromatic indole framework that can participate in hydrogen bonding and aromatic interactions. As a structurally modified amino acid, it is used as a defined building block for peptide and amino acid derivative synthesis and for structure-property studies in which indole hydroxylation is used to probe effects on conformation, labeling chemistry, or analytical behavior.
CAT No: CP24801
2-Hydroxy-L-tryptophan is a stereochemically defined L-tryptophan derivative bearing an additional hydroxyl substituent on the indole ring, providing a phenolic handle that can influence reactivity and downstream derivatization. As an amino acid building block, it is used in peptide and chemical biology workflows where indole-functionalized tryptophan analogs are required for structure-property studies, site-specific labeling strategies, or preparation of specialized standards. Its aromatic indole system and phenolic functionality make it particularly relevant for analytical method development and for constructing modified peptide motifs that probe tryptophan-centered chemistry.
1. Indole-Modified Peptide Synthesis
2-Hydroxy-L-tryptophan is used as an indole-functionalized tryptophan building block for preparing peptides that incorporate an extra hydroxyl group on the indole ring. Researchers in peptide chemistry and protein engineering use this analog to study how indole substitution affects peptide conformation, chemical stability under oxidative or derivatization conditions, and reactivity patterns at tryptophan-like sites. In custom peptide synthesis workflows, the amino acid is selected when a tryptophan surrogate with a phenolic indole substituent is needed to model or interrogate tryptophan-dependent chemical behavior in a controlled, sequence-defined context.
2. Chemical Biology Probe And Derivatization
2-Hydroxy-L-tryptophan supports chemical biology experiments that rely on indole/phenol chemistry for probe construction and downstream functionalization. Chemical biology groups use the phenolic hydroxyl on the indole scaffold as a reactive feature for preparing specialized derivatives that can be attached to biomolecular scaffolds, used as labeling precursors, or incorporated into peptide-based probes to report on local microenvironments through chemistry at the indole site. The defined L-stereochemistry and amino acid functionality also make it practical for building probe-containing peptide conjugates where site-specific placement of an indole analog is required rather than relying on non-specific aromatic modifications.
3. Analytical Standards For Indole Chemistry
2-Hydroxy-L-tryptophan is widely used as a reference material for analytical method development and targeted quantification involving indole-substituted amino acids and tryptophan-like motifs. Analytical chemists employ it to validate LC-MS workflows, calibrate response for indole/phenolic species, and support identification strategies for hydroxylated tryptophan derivatives formed during sample processing, derivatization, or chemical treatment. In metabolomics and chemical stability studies, the compound's distinct mass and functional-group pattern help distinguish hydroxylated indole species from native tryptophan and other closely related analogs, improving confidence in peak assignment and quantitation.
4. Pharmaceutical Intermediate Development
2-Hydroxy-L-tryptophan is also used as a specialty intermediate for medicinal chemistry and pharmaceutical research programs that require indole-functionalized amino acid precursors. Process development and synthetic chemistry teams incorporate this scaffold into downstream routes where an indole bearing a phenolic hydroxyl must be carried through key steps to enable further functional-group transformations. Because the molecule already contains both amino acid functionality and an activated aromatic hydroxyl on the indole ring, it is often selected when the target intermediate design benefits from retaining the indole substitution pattern early in the synthesis plan.
2. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
5. Emu oil in combination with other active ingredients for treating skin imperfections
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