Cbz-4-Nitro-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing a para (4-) nitro substituent on the aromatic side chain. The molecule contains an amino group masked as a benzyloxycarbonyl (Cbz) carbamate and a free carboxyl group, with the nitro-functionalized phenyl ring providing an electron-withdrawing handle for chemical characterization and side-chain reactivity modulation. In peptide and peptidomimetic synthesis workflows, the Cbz protection supports controlled chemoselectivity during stepwise coupling while the 4-nitro aromatic motif enables incorporation into labeled or structure-activity study analogues and facilitates analytical differentiation of the resulting intermediates or products.
CAT No: CP16109
Cbz-4-Nitro-D-Phenylalanine is a Cbz-protected, D-configured phenylalanine derivative bearing a para-nitro substituent on the aromatic ring. The molecule contains a benzyloxycarbonyl (Cbz) carbamate at the α-amino position, a free carboxyl functionality or carboxyl-derived reactivity depending on the supplied form, and a strongly electron-withdrawing nitro group that modulates aromatic electronics and downstream derivatization. The D-stereocenter at the α-carbon enables incorporation into stereochemically defined peptide sequences and chiral structure motifs. The nitro-bearing phenyl side chain can participate in selective reduction, nucleophilic aromatic substitution after activation, or further functional group interconversions, while the Cbz group supports standard peptide coupling workflows and orthogonal deprotection strategies.
1. Peptide Synthesis
Cbz-4-Nitro-D-Phenylalanine supports peptide building-block preparation for solid-phase or solution-phase peptide coupling where an N-Cbz protected amino acid is required. The Cbz carbamate stabilizes the α-amino functionality during activation and coupling, while the D-configuration provides stereochemical control for generating peptide analogs with defined chiral backbones. The para-nitro phenyl side chain can be retained through coupling to preserve electronic character, or converted after chain assembly to access nitro-reduced or further functionalized residues. Downstream peptide fragments and longer peptidic constructs can be generated for method development, stereochemical studies, and scaffold diversification in amino acid chemistry.
2. Peptidomimetics And SAR Studies
Cbz-4-Nitro-D-Phenylalanine is suitable for peptidomimetic and SAR-oriented chemical biology programs that require aromatic side-chain tuning with a strong electron-withdrawing substituent. The nitro group on the para position can influence conformational preferences, hydrogen-bonding patterns at the aromatic periphery, and reactivity toward post-synthetic transformations, enabling systematic structure-activity relationship studies. The D-amino acid stereochemistry allows access to non-natural peptide-like frameworks that can be used to probe stereochemical determinants of binding or recognition in molecular design workflows. The Cbz-protected amino acid form also facilitates controlled incorporation into analog libraries followed by side-chain conversion to generate a set of chemically related derivatives for comparative evaluation.
3. Side-Chain Functionalization
Cbz-4-Nitro-D-Phenylalanine serves as a chiral intermediate for side-chain functionalization routes that start from a nitro-activated aromatic handle. The para-nitro substituent can be transformed into amino, hydroxylamine, or other reduced and functionalized aromatic motifs under appropriate conditions, enabling access to downstream derivatives used in medicinal chemistry and chemical biology tool development. The Cbz protecting group provides a stable nitrogen protection strategy during side-chain modification planning, allowing selective manipulation of the aromatic nitro functionality while maintaining the α-amino protection state. The resulting functionalized aromatic amino acid derivatives can then be carried forward into peptide coupling, conjugation, or heteroaromatic elaboration steps.
4. Chiral Building Block Development
Cbz-4-Nitro-D-Phenylalanine is applicable as a chiral amino acid intermediate for stereoselective synthesis planning where D-configuration is a defined design variable. The D stereocenter at the α-carbon, combined with the N-Cbz protection, supports predictable behavior in peptide coupling chemistry and enables reproducible generation of stereochemically pure peptide building blocks. The aromatic nitro group provides an additional stereochemically stable substituent that can be used as a chemical "tag" for later transformation, supporting iterative synthesis of chiral libraries. The compound can therefore function as a controlled starting point for chiral scaffold construction, protected amino acid chemistry, and downstream derivatization sequences in fine chemical synthesis.
5. Pharmaceutical And Fine Chemical Intermediates
Cbz-4-Nitro-D-Phenylalanine can be employed in pharmaceutical intermediate preparation and specialty chemical production where protected amino acids with functionalizable aromatic substituents are required. The Cbz carbamate enables compatibility with common peptide-coupling activation chemistries, supporting manufacturing-relevant workflows that require protected nitrogen stability during intermediate handling. The para-nitro phenyl group provides a process-friendly functional handle for conversion into other aromatic functionalities used in API-related synthesis, linker construction, or intermediate diversification. The compound's defined stereochemistry and orthogonal protection profile make it suitable for scalable intermediate routes that culminate in protected or deprotected amino acid derivatives for further industrial chemical manufacturing steps.
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