Fmoc-3-Nitro-L-Phenylalanine is an Fmoc-protected amino acid derivative bearing a phenylalanine backbone with a nitro substituent at the 3-position of the aromatic ring, classifying it as an aromatic, non-proteinogenic substitution pattern suitable for peptide chemistry. The molecule contains both an Fmoc-protected α-amino group and a free carboxylic acid, with the side chain presenting a nitro-functionalized benzyl group that can participate in electron-withdrawing and polarity-modulating interactions while maintaining the L-configuration indicated in the name. In synthesis, it is employed as a protected building block for stepwise peptide assembly, where the Fmoc group controls chemoselectivity during coupling and the aromatic nitro handle supports structure-activity studies, labeling strategies, or analytical differentiation of nitro-substituted peptide analogues.
CAT No: CP16006
CAS No:206060-42-6
Synonyms/Alias:206060-42-6;Fmoc-Phe(3-NO2)-OH;Fmoc-L-3-Nitrophenylalanine;Fmoc-3-Nitro-L-Phenylalanine;L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-nitro-;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-nitrophenyl)propanoic acid;Fmoc-L-3-Nitrophe;MFCD01317718;(2S)-2-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)-3-(3-NITROPHENYL)PROPANOIC ACID;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(3-nitrophenyl)propanoic acid;MFCD01317715;AKOS024464828;FF50058;AC-25335;AS-54556;CS-0149878;S12019;EN300-7377722;Fmoc-L-Phe(3-NO2)-OH;Fmoc-m-nitro-L-Phe-OH;N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-nitro-L-phenylalanine;N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-3-nitrophenylalanine (Fmoc-D-Phe(3-NO2)-OH);
Fmoc-3-Nitro-L-Phenylalanine is an Fmoc-protected L-phenylalanine derivative bearing a nitro group at the 3-position of the aromatic ring, combining a chiral amino acid core with an electronically activated side chain. The molecule contains an N-Fmoc carbamate that supports standard solid-phase or solution-phase peptide assembly, along with a free carboxyl functionality suitable for conversion to peptide-coupling intermediates. The aromatic nitro substituent introduces strong electron-withdrawing character and a polar handle that can participate in further derivatization, including reduction to an aniline or transformation to other nitrogen-containing substituents. The stereodefined L-configuration at the alpha carbon and the stable aromatic substitution pattern make the compound a targeted chiral building block for preparing nitro-phenylalanine-containing peptides and related research intermediates.
1. Peptide Synthesis
Fmoc-3-Nitro-L-Phenylalanine is used in peptide synthesis workflows for incorporating nitro-substituted phenylalanine residues into peptide chains. The Fmoc-protected amine enables controlled N-deprotection strategies under base-mediated conditions, while the amino acid backbone supports coupling chemistry to form amide bonds at the alpha-carboxylate. The 3-nitro aromatic side chain can be retained through peptide assembly to yield nitro-bearing peptide analogs for downstream functional studies. The resulting peptides serve as defined substrates for biochemical assays, as molecular probes in chemical biology, and as sequence-specific building blocks for peptidomimetic construction.
2. Side-Chain Functionalization
Fmoc-3-Nitro-L-Phenylalanine is applied to side-chain functionalization strategies where the nitro group functions as a chemically transformable aromatic handle. The electron-withdrawing nitro substituent can undergo selective reduction to an aniline, enabling subsequent coupling reactions such as diazo-related transformations or formation of substituted aromatic motifs. The presence of the Fmoc group allows the compound to be handled as a protected amino acid intermediate during synthesis, with deprotection enabling conversion into peptide-bound or free amino acid derivatives. Downstream transformations can generate nitro-to-amino conversion products, enabling access to new aromatic substitution patterns for SAR studies and synthetic organic chemistry campaigns.
3. Chemical Biology Probes
Fmoc-3-Nitro-L-Phenylalanine is used in chemical biology and molecular recognition research to install a defined nitro-phenylalanine residue into peptide scaffolds. The stereochemically defined L-amino acid and the rigid phenyl side chain support consistent conformational behavior in peptide contexts, while the nitro group provides a polar, electron-deficient aromatic feature that can influence binding interactions and spectroscopic properties. The Fmoc-protected form supports incorporation into longer sequences via peptide coupling, enabling generation of sequence-defined probes for studying substrate recognition, binding-site preferences, or interaction networks. The resulting nitro-containing peptides can be further derivatized after assembly to produce amino-functional analogs for conjugation or labeling chemistry.
4. SAR Studies
Fmoc-3-Nitro-L-Phenylalanine is suitable for structure-activity relationship studies in medicinal chemistry and peptidomimetic design where aromatic electronics and side-chain polarity are systematically varied. The 3-nitro substitution pattern provides a specific electronic perturbation relative to unsubstituted phenylalanine, while the L-configuration maintains stereochemical consistency across analog series. Fmoc-based peptide building block preparation enables parallel synthesis of nitro-bearing variants and comparative evaluation of how side-chain substitution affects molecular recognition. Downstream conversion of the nitro group to other functional aromatic groups can support iterative SAR cycles that map electronic and hydrogen-bonding contributions within peptide-like scaffolds.
5. Pharmaceutical Intermediate Preparation
Fmoc-3-Nitro-L-Phenylalanine is employed as a chiral, protected amino acid intermediate for manufacturing-related fine chemical synthesis of nitro-phenylalanine-containing peptide fragments. The N-Fmoc carbamate supports robust handling and controlled deprotection during intermediate stage processing, while the amino acid framework can be converted into coupling-ready forms for fragment assembly. The nitro aromatic functionality can be carried through protected stages and then transformed in later steps to access downstream arylamine or substituted aromatic intermediates used in broader synthesis programs. Process chemistry teams can leverage the defined stereochemistry and protected-group strategy to design scalable routes to peptide intermediates and related chiral building blocks.
6. Analytical Research Standards
Fmoc-3-Nitro-L-Phenylalanine is used in analytical research and method development as a structurally defined reference material for peptide and amino acid analysis. The combination of Fmoc protection and the nitro-substituted aromatic side chain provides distinct chromatographic and spectrometric signatures that can support identification and quantitation of nitro-phenylalanine-containing species. The stereodefined L-amino acid structure enables consistent behavior in derivatization and detection workflows, including monitoring of peptide coupling outcomes and impurity profiling. The compound can also serve as a starting point for generating labeled or transformed standards derived from nitro-to-amino conversion, supporting robust analytical coverage across synthetic and downstream processing steps.
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