DL-4-Nitrophenylglycine is a non-proteinogenic, aromatic amino acid derivative in which a glycine backbone bears a 4-nitrophenyl substituent at the alpha-carbon, forming a substituted phenylglycine scaffold. The molecule contains both an amino group and a carboxyl group while the side chain features a nitro-substituted phenyl ring that provides an electron-withdrawing aromatic functionality, and the "DL" designation indicates a racemic mixture of stereochemical forms at the chiral center. DL-4-Nitrophenylglycine is used in peptide and amide synthesis as a substituted amino acid building block for structure-activity studies, and the nitro-bearing aromatic moiety can serve as a spectroscopic handle in analytical method development and chemical biology labeling workflows where an aromatic nitro group is compatible.
CAT No: CP10501
DL-4-Nitrophenylglycine is a glycine-based amino acid derivative in which the side chain is a para-nitrophenyl substituent, yielding an aromatic, strongly electron-withdrawing nitro group that modulates both electrophilicity and hydrogen-bonding behavior. The molecule contains an amino functionality and a carboxylic acid (or acid-form equivalent) that support standard amino acid coupling chemistry, while the nitro-substituted phenyl ring provides a handle for redox transformations, nucleophilic aromatic substitution under activated conditions, and spectroscopically detectable aromatic chromophores. The DL designation indicates a racemic mixture at the glycine stereocenter, which is relevant for experiments where stereochemical effects are evaluated or where racemate processing is acceptable before chiral resolution or asymmetric conversion. Aromatic nitro functionality also enables downstream derivatization into amino, hydroxylamine, or substituted anilines that can be carried into peptide analogs, enzyme probes, and industrial fine-chemical intermediates.
1. Peptide Coupling
DL-4-Nitrophenylglycine is applied in peptide synthesis workflows as a glycine-derived, aromatic side-chain amino acid that can participate in amide bond formation through its carboxyl group using common peptide coupling strategies. The free amino and carboxylic acid functionalities can be managed via N-protection and, when required, temporary side-chain compatibility controls to prevent nitro-group side reactions during activation and coupling. The para-nitrophenyl motif can be retained through protected amino acid assembly to furnish peptide building blocks for structure-activity relationship studies and peptidomimetic scaffolds. The resulting nitro-bearing peptide analogs can then be converted to corresponding anilines or related derivatives for downstream library diversification in solid-phase or solution-phase synthesis.
2. Chiral Resolution Studies
DL-4-Nitrophenylglycine is suitable for stereochemical research and chiral building block development because the racemic mixture at the glycine stereocenter enables direct comparison of diastereomeric outcomes after resolution or stereoselective derivatization. The nitro-substituted phenyl ring provides an aromatic chromophore that can support analytical monitoring of stereochemical enrichment by UV-Vis and chromatographic methods, while the amino acid core supports formation of diastereomeric salts or derivatives. The compound can serve as a starting point for preparing enantiomerically enriched analogs that are then incorporated into peptide frameworks to probe stereochemical influence on binding, conformation, or enzymatic recognition. Downstream use commonly includes conversion of the nitro group to an aniline or other functionalized aromatic moieties while preserving the stereochemical information established during resolution.
3. Enzyme Probe Development
DL-4-Nitrophenylglycine is used in chemical biology and enzyme studies as an amino acid analog bearing a para-nitrophenyl group that can participate in substrate recognition and can undergo nitro-related redox or reduction pathways in mechanistic experiments. The amino acid backbone supports incorporation into substrate mimics, inhibitors, or mechanistic probes where the carboxylate and amino functionality contribute to binding orientation and key hydrogen-bonding interactions. The nitro group can function as a spectroscopic reporter or as a reactive handle for generating downstream aromatic amine derivatives that may alter enzyme affinity or enable derivatization for detection. The compound's racemic nature can be leveraged in preliminary mapping studies to identify whether stereochemical discrimination is required before advancing to enantiopure probe design.
4. Aromatic Nitro Derivatization
DL-4-Nitrophenylglycine is employed in synthetic organic chemistry and industrial fine chemical synthesis as a nitro-functionalized amino acid intermediate for functional group transformation. The para-nitrophenyl nitro group can be converted under controlled conditions into amino, hydroxylamine, or substituted aniline derivatives, enabling access to broader chemical space while retaining the amino acid core for further coupling or protection/deprotection sequences. The carboxylic acid and amino functionality facilitate conversion into activated esters, amides, or protected amino acid derivatives that can be carried into multi-step manufacturing routes. Downstream products derived from these transformations can serve as intermediates for peptidomimetics, heteroaryl-containing analogs, and other nitrogen-containing aromatic building blocks.
5. Analytical Standard And Method Development
DL-4-Nitrophenylglycine is applicable to analytical research and method development where an amino acid with a strongly absorbing nitroaromatic chromophore is needed as a reference material. The combination of an amino acid functional set and a para-nitrophenyl nitro group supports robust detection by UV-Vis and can improve signal-to-noise in chromatographic workflows designed for amino acid derivatization or peptide hydrolysate profiling. The racemic composition can be advantageous for calibrations that require total concentration measurement without enforcing enantiomeric separation, while the nitro group provides chemical stability under many analytical conditions. The compound can also be used to qualify derivatization reagents and detection schemes for amino acid esterification, N-protection checks, or peptide coupling monitoring in applied peptide science and process chemistry contexts.
6. Pharmaceutical Intermediate Preparation
DL-4-Nitrophenylglycine is relevant to pharmaceutical intermediate preparation and process chemistry because it combines an amino acid scaffold with an aromatic nitro handle that can be carried through protective group strategies into downstream drug-like fragments. The amino acid core supports conversion into N-protected derivatives and activated forms suitable for incorporation into larger molecules, while the nitro group provides a controlled transformation point toward anilines and related aromatic functionalities used in medicinal chemistry. The stereocenter racemate can be processed through resolution, stereoselective conversion, or parallel synthesis routes depending on the target's stereochemical requirements. The compound therefore functions as an amino acid-based intermediate enabling the construction of substituted aromatic motifs within peptide-like structures and other nitrogen-containing intermediates used in specialty chemical manufacturing.
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