D-4-Nitrophenylglycine is a D-configured non-proteinogenic amino acid derivative featuring a glycine backbone substituted with a 4-nitrophenyl side chain, classifying it as an aromatic, nitro-functional amino acid. The molecule contains a primary amino group and a carboxylic acid functional group, while the aromatic ring bears a nitro substituent that provides strong electron-withdrawing character and a polar, redox-active group for chemical characterization. In synthetic and chemical biology workflows, it is used as a defined building block for preparing peptide analogues and other amino acid conjugates, and its nitro-bearing aromatic motif can serve as a functional handle for structure-activity studies and analytical method development.
CAT No: CP10503
D-4-Nitrophenylglycine is a chiral amino acid derivative featuring a glycine backbone substituted at the alpha-carbon with a para-nitrophenyl ring, giving a stereodefined D-configuration at the amino acid center. The molecule contains an amino functionality and a carboxylic acid (or, depending on the supplied form, a corresponding protected/derivatized acid), while the aromatic side chain bears a strongly electron-withdrawing nitro group that modulates acidity, hydrogen-bonding behavior, and electrophilic aromatic reactivity. The nitrophenyl substituent enables spectroscopic detectability and serves as a handle for downstream transformations such as reduction to an aniline or participation in aromatic substitution chemistry. As a chiral building block, D-4-nitrophenylglycine can be incorporated into peptide-like frameworks or used as a stereochemical intermediate for amino acid derivatization and structure-controlled synthetic elaboration.
1. Chiral Amino Acid Intermediate
D-4-Nitrophenylglycine is applied in chiral synthesis and medicinal chemistry intermediate preparation where the D-stereocenter and nitro-substituted phenyl group provide a defined three-dimensional scaffold for stereoselective downstream steps. The amino acid functionality supports conversion to N-protected derivatives and activation of the carboxyl group for coupling, while the para-nitro substituent can be retained for polarity tuning or transformed later to access anilines and related aromatic motifs. Stereochemical integrity can be leveraged during peptide coupling chemistry or for constructing chiral analogs used in structure-activity relationship studies. The resulting derivatives function as practical chiral amino acid intermediates for fine chemical synthesis and stereocontrolled molecular design.
2. Peptide Coupling Chemistry
D-4-Nitrophenylglycine is suitable for peptide building block preparation and peptide coupling chemistry in research-grade synthesis where the amino acid backbone enables standard amide bond formation. The carboxylic acid and amino group can be managed through protection strategies such as N-protection and carboxyl activation, allowing incorporation into peptide fragments with the D-configuration preserved at the alpha-carbon. The para-nitrophenyl side chain contributes aromatic character and strong electronic effects that can influence coupling outcomes, conformational preferences, and analytical detectability of the resulting peptide analogs. Peptide-like constructs incorporating D-4-nitrophenylglycine can be used to generate stereochemically defined analog libraries and to probe how aromatic nitro substitution affects molecular recognition.
3. Peptidomimetic And SAR Studies
D-4-Nitrophenylglycine is used in peptidomimetic construction and SAR studies where the glycine-derived backbone and the para-nitrophenyl substituent provide a compact, stereodefined motif for structure-controlled analog generation. The nitro group can serve as a functional handle for subsequent chemical manipulation, including reduction to an aniline or conversion to other aromatic functionalities, enabling systematic exploration of electronic and hydrogen-bonding contributions. The amino acid framework supports derivatization into amide, ester, or protected forms that can be incorporated into constrained scaffolds or used to build non-natural peptide analogs. Downstream products derived from D-4-nitrophenylglycine can be employed as research intermediates for mapping structure-function relationships in applied molecular design workflows.
4. Analytical Standards Development
D-4-Nitrophenylglycine is applicable to analytical research and method development because the para-nitrophenyl group provides strong UV/visible response and characteristic chromatographic behavior for chiral and achiral separation workflows. The presence of a defined stereocenter allows its use as a reference material for stereochemical verification of related amino acid derivatives and peptide building blocks. The amino acid functionality enables formation of derivatization products used to assess coupling efficiency, stability, or identity in synthetic sequences, including monitoring of protected amino acid intermediates. Analytical standards and labeled or derivatized analogs prepared from D-4-Nitrophenylglycine can support quality control and characterization in synthetic organic chemistry and biochemical research intermediate handling.
5. Aromatic Functional Group Transformation
D-4-Nitrophenylglycine is employed as a chemical-manufacturing intermediate for aromatic functional group transformation where the nitro substituent enables controlled conversion to more reactive or differently polar aromatic groups. The nitro group can be reduced to an aniline or further functionalized through established aromatic chemistry, while the amino acid backbone allows temporary protection to prevent side reactions during these transformations. The stereodefined D-amino acid core can be carried through multi-step sequences to yield chiral aromatic amino derivatives that serve as feedstocks for downstream fine chemical synthesis. The resulting aromatic amino acid derivatives can then be used for constructing new chiral scaffolds, preparing conjugation-ready intermediates, or supplying building blocks for industrial specialty chemical production.
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