D-2-Hydroxy-5-nitro-Phenylalanine is a D-configured, non-proteinogenic aromatic amino acid featuring a benzyl side chain substituted with a hydroxyl group at the 2-position and a nitro group at the 5-position, while retaining the α-amino and α-carboxyl functionality. The molecule contains a primary amino group and a carboxylic acid that can form zwitterionic species, and the side-chain hydroxyl and nitro substituents provide hydrogen-bonding and strong electron-withdrawing character that can influence aromatic reactivity and peptide-coupling behavior. In synthetic and chemical biology workflows, this amino acid is used as a defined building block for preparing modified peptides and as a structural probe in structure-activity studies or labeling strategies where an aromatic hydroxyl/nitro motif is required.
CAT No: CP14903
D-2-Hydroxy-5-nitro-Phenylalanine is a chiral phenylalanine derivative bearing a D-configured stereocenter at the alpha carbon, a benzylic 2-hydroxy substituent on the aromatic ring, and a 5-nitro group that strongly modulates ring electronics and polarity. The amino acid framework presents a primary amino functionality and a carboxylic acid (or, depending on the supplied form, a protected/activated equivalent), enabling standard amino acid coupling chemistry while the phenolic-like hydroxyl and nitro substituents participate in hydrogen bonding, redox, and electrophile-stabilizing interactions. The nitro group can be used as a stable handle for controlled transformations, while the aromatic hydroxyl can be leveraged for selective derivatization and downstream functional group interconversion. As a chiral amino acid intermediate, D-2-Hydroxy-5-nitro-Phenylalanine can be incorporated into peptide-like scaffolds or used to build stereodefined aromatic amino acid analogs for structure-function investigations.
1. Peptide Synthesis
D-2-Hydroxy-5-nitro-Phenylalanine supports peptide building-block workflows in peptide synthesis and automated solid-phase or solution-phase coupling strategies. The protected amino acid derivative form can be acylated at the alpha-carboxylate while the aromatic 2-hydroxy and 5-nitro substituents remain compatible with amide bond formation when appropriate orthogonal protection is selected. Nitro and hydroxyl substituents provide additional sites for post-coupling modification, enabling access to nitro-reduced, hydroxyl-derivatized, or cyclized analogs that preserve the D-stereochemical integrity. Resulting D-configured peptide fragments can be used to probe aromatic electronics and hydrogen-bonding effects in peptide backbones and peptidomimetics.
2. Side-Chain Functionalization
D-2-Hydroxy-5-nitro-Phenylalanine is suited for side-chain functionalization and aromatic substitution chemistry where the nitro group and ring hydroxyl act as transformation handles. The nitro substituent can undergo controlled reduction to an aniline or further functionalization steps, while the ring hydroxyl can be converted into ethers, esters, or protected phenol derivatives to tune solubility and reactivity. The chiral amino acid scaffold maintains stereochemical definition during derivatization, supporting downstream synthesis of stereopure aromatic amino acid analogs for SAR studies. The resulting functionalized derivatives can serve as intermediates for complex heteroaromatic or conjugatable motifs used in chemical biology and synthetic organic chemistry.
3. Chiral Building Blocks
D-2-Hydroxy-5-nitro-Phenylalanine functions as a chiral amino acid intermediate for stereoselective synthesis of D-configured aromatic pharmacophores and peptide-like ligands. The D-configured alpha stereocenter enables incorporation into chiral sequences where stereochemical inversion or racemization control is required, and the aromatic substituents provide distinct electronic signatures that can influence binding and conformational preferences. Orthogonal protecting-group strategies for the amino and hydroxyl functionalities can be applied to manage chemoselectivity across multi-step syntheses, including coupling, deprotection, and selective functional group conversion. Chiral derivatives derived from this scaffold can be employed in fragment-based molecular design, stereochemical mapping, and the construction of stereodefined libraries.
4. Chemical Biology Probes
D-2-Hydroxy-5-nitro-Phenylalanine can be applied to chemical biology research as an amino acid-based probe for studying aromatic substituent effects in protein and peptide contexts. The nitro group and ring hydroxyl enable incorporation into labeled or reactive analogs that can participate in hydrogen bonding and polarity-driven recognition, while the amino acid backbone supports enzymatic or chemical incorporation into target biomolecule fragments when compatible protection strategies are used. Post-incorporation transformations, such as nitro-to-amino conversion or hydroxyl derivatization, can be used to generate reactive handles for subsequent conjugation or analytical readouts. The D-stereochemistry provides a means to evaluate stereochemical contributions to molecular recognition and to generate non-native aromatic amino acid variants for biochemical assays.
5. Pharmaceutical Intermediate Preparation
D-2-Hydroxy-5-nitro-Phenylalanine is relevant to pharmaceutical intermediate preparation within fine chemical synthesis routes that require stereopure aromatic amino acid building blocks. The compound's amino acid functionality supports conversion into activated coupling forms, while the nitro and hydroxyl substituents can be carried through intermediate stages and transformed under controlled conditions to access aniline, phenoxy, or further elaborated aromatic motifs. Protecting-group planning for the amino and hydroxyl groups can be integrated into process chemistry to maintain chemoselectivity across sequential steps that build complex drug-like scaffolds. D-configured derivatives generated from this intermediate can be used to assemble peptide-conjugated candidates, peptidomimetic fragments, or aromatic amino acid-containing intermediates used in downstream manufacturing workflows.
6. Analytical Standards
D-2-Hydroxy-5-nitro-Phenylalanine can serve as an analytical research standard and reference material for method development targeting nitro-substituted aromatic amino acids and their stereochemical variants. The defined D-configuration and presence of both nitro and hydroxyl functionalities provide characteristic chromatographic and spectroscopic signatures that support identification in LC-MS, HPLC, and related analytical workflows. Derivatization of the hydroxyl group or controlled transformation of the nitro group can generate additional reference species for confirming selectivity, stability, and conversion pathways during synthesis or quality control. Chiral amino acid analytics benefit from such reference compounds when monitoring protected amino acid synthesis, peptide coupling outcomes, and downstream functional group transformations.
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