Cbz-3-Nitro-D-Phenylalanine is a Cbz-protected, D-configured phenylalanine derivative bearing a 3-nitro substituent on the aromatic ring, placing it in the class of non-natural, ring-functionalized amino acids used for peptide building blocks. The molecule contains an N-terminal benzyloxycarbonyl (Cbz) carbamate that masks the α-amino group and a free α-carboxyl group, while the side chain features a nitro-functionalized benzyl moiety that can participate in electron-withdrawing interactions and provides a distinct handle for structure-property studies. In synthesis, it is employed as a protected amino acid for incorporation into peptides or peptide-like constructs where the aromatic 3-nitro group enables chemical labeling, conjugation planning, or analytical differentiation of the resulting sequence or derivative.
CAT No: CP16009
Cbz-3-Nitro-D-Phenylalanine is a D-configured phenylalanine derivative bearing a Cbz (benzyloxycarbonyl) carbamate on the amino group and a 3-nitro substituent on the aromatic ring. The molecule combines a stereogenic center at the amino acid alpha carbon with an electron-deficient nitroaryl side chain that can participate in redox and nucleophilic aromatic substitution chemistry under appropriate conditions. The Cbz-protected amine supports controlled peptide coupling and orthogonal deprotection strategies, while the aromatic nitro group provides a handle for downstream functional group interconversion. As a chiral amino acid intermediate, it is suited to building stereochemically defined peptide analogs and aryl-functionalized derivatives used in structure-focused synthetic and analytical workflows.
1. Protected Amino Acids
Cbz-3-Nitro-D-Phenylalanine is applied in protected amino acid synthesis workflows where carbamate protection enables reliable peptide coupling chemistry while maintaining the D-stereochemical configuration. The Cbz group stabilizes the amino functionality during activation and acyl transfer steps, and the nitro-substituted phenyl side chain remains a defined substituent for later transformation or incorporation into larger scaffolds. Orthogonal deprotection of the Cbz moiety can be used to generate a reactive amino terminus for sequential coupling, allowing controlled N-terminal elaboration in multi-step syntheses. The resulting protected amino acid intermediate supports stereodefined peptide building block preparation and downstream derivatization of the aromatic side chain.
2. Peptide Synthesis
Cbz-3-Nitro-D-Phenylalanine is suitable for peptide synthesis and peptide analog construction where a protected D-amino acid residue is required to introduce stereochemical diversity and aromatic electronic modulation. The Cbz-protected amine participates as the N-acylation partner after activation, while the carboxylate functionality of the amino acid framework enables amide bond formation to neighboring residues. The meta-nitro substituent on the phenyl side chain can influence local conformational preferences and can serve as a functional handle for later conversion to amino, hydroxylamino, or other aryl derivatives depending on the synthetic plan. Incorporation of this residue supports the preparation of D-containing peptides for biochemical research, SAR studies, and mechanistic investigations of peptide structure and side-chain electronics.
3. Side-Chain Functionalization
Cbz-3-Nitro-D-Phenylalanine is used in side-chain functionalization strategies that leverage the nitroaryl group as a reactive precursor for further chemical conversion. The nitro substituent can be transformed into alternative functional motifs while the Cbz-protected amino group helps preserve peptide-compatible functionality during the sequence. Aromatic nitro chemistry enables access to amine-bearing analogs and related derivatives that can be used to tune hydrogen-bonding patterns, polarity, and reactivity in subsequent coupling or conjugation steps. Downstream generation of aryl-functionalized amino acid derivatives supports fine chemical synthesis, peptidomimetic diversification, and the preparation of labeled or tagged analogs for analytical and molecular recognition studies.
4. Chemical Biology Probes
Cbz-3-Nitro-D-Phenylalanine is applied in chemical biology research where stereodefined, nitro-functionalized amino acid residues can be incorporated into peptide-based probes and molecular recognition elements. The D-configuration at the alpha carbon supports studies requiring non-proteinogenic stereochemistry to probe binding modes, protease resistance, or conformational effects in peptide scaffolds. The electron-deficient nitroaryl side chain can serve as a chemical handle for subsequent derivatization toward probe-ready functionalities, while the Cbz-protected amine supports controlled assembly of probe sequences. The resulting D-nitroaryl peptide components can be used to generate structure-focused reagent libraries for biochemical assays, imaging reagent development, and mechanistic interrogation of peptide interactions.
5. Process Chemistry Intermediate
Cbz-3-Nitro-D-Phenylalanine is relevant to process chemistry intermediate preparation where stable N-protection and a defined aromatic nitro substituent support scalable synthetic planning. The Cbz carbamate provides a robust protecting-group platform that can withstand common coupling and purification steps before targeted deprotection, supporting manufacturing-oriented route design for protected amino acid derivatives. The nitro group enables downstream conversion to other aryl functionalities without altering the core amino acid stereocenter, which is critical for consistent intermediate specifications. Utilization of this compound in intermediate synthesis supports specialty chemical production and provides a controlled chiral building block for downstream peptide construction and functional aryl derivative manufacturing.
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