DL-2-Hydroxy-5-nitro-Phenylalanine is a non-proteinogenic, aromatic amino acid derivative featuring a phenylalanine backbone bearing an ortho hydroxy substituent and a nitro group at the 5-position, with the alpha-amino and alpha-carboxyl functional groups present as free functionalities in the DL stereochemical mixture. The side chain contains a phenolic hydroxyl capable of hydrogen bonding and a nitro substituent that is strongly electron-withdrawing, while the "DL" designation indicates a racemic mixture of stereoisomers at the alpha carbon. This molecule is used in peptide and amino acid analogue synthesis and in chemical biology studies where nitro- and hydroxy-functional aromatic side chains provide handles for structure-activity investigations, conjugation strategies, or analytical method development.
CAT No: CP14901
DL-2-Hydroxy-5-nitro-Phenylalanine contains a phenylalanine backbone bearing a benzylic 2-hydroxy substituent and a 5-nitro group on the aromatic ring, providing two oxygen-bearing functionalities and a strongly electron-withdrawing nitro handle. The molecule exists as a racemic (DL) mixture at the α-amino stereocenter, which supports stereochemical studies and chiral resolution workflows when paired with appropriate derivatization or asymmetric synthesis strategies. The amino and hydroxyl groups enable controlled protection/deprotection sequences, while the nitro group can participate in redox transformations and downstream functionalization to access anilines, heteroaryl motifs, or further substituted aromatic systems. As an amino acid derivative intermediate, it can be incorporated into peptide-like constructs after conversion to an activated protected form, and it can also serve as a chemically defined aromatic scaffold for structure-function investigations.
1. Protected Amino Acid Chemistry
DL-2-Hydroxy-5-nitro-Phenylalanine serves as a practical feedstock for protected amino acid synthesis in peptide coupling chemistry, where the α-amino functionality can be masked as an N-protecting group and the α-hydroxyl can be selectively protected to tune reactivity. The aromatic 5-nitro substituent remains chemically informative during many coupling steps, enabling orthogonal transformations after peptide assembly or during late-stage diversification. Racemic stereochemistry supports process development and method screening for protecting-group compatibility, including strategies that preserve the benzylic hydroxyl for subsequent functional group interconversions. Downstream, protected derivatives can be used to generate peptide building blocks and amino acid ester or amide intermediates for fine chemical synthesis and research-grade scaffold construction.
2. Peptide Synthesis Building Block
DL-2-Hydroxy-5-nitro-Phenylalanine can be converted into an N-protected amino acid derivative suitable for standard peptide coupling approaches, enabling incorporation into peptide sequences or peptide analogs where an aromatic, hydroxylated side chain is required. The presence of both an amino group and a benzylic hydroxyl supports formation of amide linkages while providing a handle for intramolecular hydrogen-bonding patterns and post-coupling derivatization. The nitro group can be retained through peptide assembly and then transformed to modulate aromatic electronics or to introduce new functional groups for SAR studies. Resulting peptide-like products can be used as defined substrates or molecular probes in biochemical research, as well as intermediates for peptidomimetic construction in synthetic organic chemistry.
3. Chiral Resolution And SAR Studies
DL-2-Hydroxy-5-nitro-Phenylalanine supports stereochemical research workflows because its DL form provides a clear starting point for chiral resolution, enantiomer derivatization, or asymmetric conversion to single-enantiomer analogs. The α-stereocenter and the benzylic hydroxyl create stereochemically sensitive functional groups that can be used to generate diastereomeric derivatives for analytical separation and structure-activity relationship studies. The 5-nitro substituent offers a chemically transformable aromatic feature, enabling redox-driven access to anilines or further substituted aromatic systems that can be correlated with binding or reactivity trends. Enantiopure or stereochemically enriched derivatives derived from this racemate can be applied to SAR-driven molecular design, fragment optimization, and mechanistic studies in chemical biology.
4. Nitro-to-Amine Diversification
DL-2-Hydroxy-5-nitro-Phenylalanine is well suited for downstream aromatic functionalization strategies where the nitro group acts as a synthetic switch for converting to an aniline or related reduced products. The retained hydroxyl functionality can be leveraged to control chemoselectivity during sequential transformations, including formation of additional conjugation-ready groups after nitro reduction. The amino acid framework provides a convenient platform for generating functional intermediates such as amino-substituted aromatic derivatives that can be reprotected, esterified, or coupled into larger molecules. This diversification pathway enables access to chemically defined building blocks for medicinal chemistry-like scaffold exploration, heteroaryl synthesis routes, and industrial fine chemical intermediate preparation.
5. Analytical Standards and Method Development
DL-2-Hydroxy-5-nitro-Phenylalanine can function as a reference compound for analytical method development targeting amino acid derivatives that contain both hydroxyl and nitro-substituted aromatic motifs. The racemic composition supports calibration and validation of chiral or achiral chromatographic workflows, particularly when monitoring protected amino acids, peptide hydrolysates, or derivatized amino acid fractions. The nitro group provides strong detectability under multiple instrumental conditions, while the hydroxyl and amino functionalities enable derivatization approaches that improve signal response or chromatographic behavior. Generated analytical standards and derivative forms can support quality control in peptide intermediate manufacturing, research intermediate tracking, and biochemical sample analysis where amino acid building blocks are quantified or characterized.
6. Specialty Chemical Production
DL-2-Hydroxy-5-nitro-Phenylalanine can be employed in specialty chemical production as an amino acid-based aromatic intermediate for constructing hydroxylated aniline derivatives and related substituted aromatic building blocks. The combination of an amino acid backbone with a nitro-activated aromatic ring enables process-oriented route design in which protecting-group selection and staged functional transformations can be coordinated to manage chemoselectivity. The benzylic hydroxyl can be conserved, protected, or converted depending on the target downstream chemistry, supporting manufacturing flexibility for generating peptide-ready intermediates or non-peptidic aromatic derivatives. Industrially relevant downstream uses include preparation of fine chemical intermediates for chemical manufacturing and applied synthesis of functional aromatic materials derived from amino acid chemistry.
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