D-2-Hydroxykynurenine is a non-proteinogenic hydroxylated kynurenine derivative, featuring an aromatic heterocycle linked to a side chain that bears a carboxylic acid and a stereogenic center designated as D. The molecule contains both amino and carboxyl functional groups along with a phenolic hydroxyl at the 2-position, enabling hydrogen-bonding and acid-base behavior that can influence its incorporation into peptide-like constructs or its performance in analytical separations. As a chemically defined amino acid analogue, it is used in chemical biology and biochemical research contexts such as enzyme-substrate studies, isotopic labeling workflows, and method development for monitoring kynurenine-pathway related metabolites or hydroxylated aromatic amino acid derivatives.
CAT No: CP22005
D-2-Hydroxykynurenine is a D-configured hydroxylated kynurenine derivative that retains the aromatic heteroaryl scaffold of the kynurenine family while introducing a secondary alcohol at the 2-position relative to the ring system. The molecule bears multiple hydrogen-bonding functionalities, including a phenolic or heteroaryl-compatible hydroxyl motif and an amino acid-like side-chain pattern that can be handled as a polar chiral intermediate in synthetic and biochemical workflows. The defined stereochemistry at the hydroxyl-bearing center governs conformational preferences and can influence reactivity in derivatization, oxidation/reduction, and protecting-group installation. As a chiral amino acid-derived metabolite analog, D-2-hydroxykynurenine can function as a chemically tractable intermediate for building labeled standards, enzyme probes, and downstream heterocycle or side-chain modified kynurenine derivatives.
1. Enzyme Mechanism Studies
D-2-Hydroxykynurenine is applied in biochemical research focused on enzyme mechanism elucidation within kynurenine-pathway chemistry, where stereochemical fidelity at the hydroxyl-bearing carbon is essential for meaningful substrate recognition. The chiral secondary alcohol and adjacent functional groups can participate in hydrogen-bonding networks that mimic natural metabolite binding modes in vitro. The compound can be derivatized to support kinetic studies, affinity reagent preparation, or mechanistic trapping strategies that rely on controlled functional group reactivity. Downstream use frequently includes generating metabolite analogs and reference materials that support interpretation of enzyme-catalyzed transformations in amino acid-derived pathways.
2. Chemical Biology Probes
D-2-Hydroxykynurenine serves chemical biology workflows that require chiral metabolite probes for target engagement studies and pathway mapping in vitro. The polar hydroxyl functionality and aromatic heterocycle enable selective chemical modification routes, including protected hydroxyl strategies for sequential functionalization and conjugation handle installation. The compound's stereochemistry can be preserved during derivatization to maintain biologically relevant recognition features when used as a probe scaffold. Resulting derivatives can be employed as binding reagents, pull-down-compatible analogs, or competition standards for studies of amino acid metabolite recognition and transport.
3. Analytical Standards And Labeling
D-2-Hydroxykynurenine is suitable for analytical research as a chiral reference standard for chromatographic separation and method validation in metabolomics and targeted quantification of kynurenine-related species. The defined D-configuration and hydroxyl-bearing stereocenter support reproducible retention behavior and enable discrimination from epimers or positional isomers when derivatized or analyzed under chiral conditions. The functional groups can be used to prepare derivatized standards for MS detection, including workflows that enhance ionization or stabilize the alcohol during sample handling. Downstream applications include isotope-labeling-compatible intermediate preparation and calibration material generation for routine analytical measurement of amino acid derivative metabolites.
4. Peptidomimetic And SAR Building
D-2-Hydroxykynurenine is used in medicinal chemistry and SAR studies as a chiral fragment that can be incorporated into peptidomimetic or metabolite-inspired scaffolds. The aromatic heterocycle provides a rigid recognition element, while the secondary alcohol enables stereocontrolled substitution patterns that can be carried into side-chain functionalization strategies. Protecting-group logic for the hydroxyl group can support selective coupling to electrophiles or coupling partners without perturbing the aromatic core. Downstream utility includes producing analog libraries where stereochemistry and hydroxyl placement are systematically varied to probe molecular recognition in amino acid-derived chemical space.
5. Chiral Intermediate For Derivatization
D-2-Hydroxykynurenine functions as a chiral amino acid-derived intermediate for synthetic organic chemistry routes that require stereodefined hydroxylated kynurenine derivatives. The secondary alcohol can be protected for orthogonal reactivity, enabling selective transformations at other functional sites while maintaining the D-configuration through multi-step sequences. The heteroaryl framework can support further functional group interconversions, including oxidation-state adjustments and side-chain elaboration to access additional metabolite analogs. Downstream manufacture-oriented use includes preparing fine chemical intermediates for specialty synthesis programs and supporting process chemistry development where chiral control and functional group compatibility govern route design.
6. Pharmaceutical Intermediate Development
D-2-Hydroxykynurenine is applicable to pharmaceutical intermediate preparation for programs that require metabolite-like chiral scaffolds and hydroxyl-bearing stereocenters for downstream medicinal chemistry. The molecule's polar functionality and aromatic heterocycle can be leveraged to install protected groups that enable subsequent coupling, salt formation, or conversion into more stable derivatives suitable for synthetic continuation. The D-stereochemistry provides a defined starting point for generating stereopure analogs used in structure-activity relationship exploration and lead optimization chemistry. Broader downstream relevance includes supporting specialty chemical production of chiral intermediates used across amino acid derivative synthesis and applied peptide-science adjacent scaffold construction.
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