Cbz-3-Nitro-L-Phenylalanine is a Cbz-protected, L-configured aromatic amino acid derivative in which the phenyl side chain bears a 3-nitro substituent, classifying it as a nitro-substituted phenylalanine analogue for peptide chemistry. The molecule contains a free carboxyl group and an N-terminus protected by a benzyloxycarbonyl (Cbz) carbamate, while the side chain features an electron-withdrawing nitro group that can influence aromatic reactivity and noncovalent interactions during synthesis. In research workflows, this protected amino acid is employed as a building block for controlled incorporation of 3-nitro phenylalanine residues into peptides and peptide-related intermediates, including solid-phase or solution-phase assembly where the Cbz group helps manage chemoselectivity of the amino functionality.
CAT No: CP16008
Cbz-3-Nitro-L-Phenylalanine is an N-Cbz protected L-phenylalanine derivative bearing a nitro group at the meta position of the aromatic ring, giving a chiral amino acid framework with a benzylic carbamate and a side-chain aryl nitro functionality. The stereogenic center at the alpha carbon is fixed as the L-configuration, supporting stereochemically defined peptide coupling and downstream transformations. The carbamate-protected amine reduces undesired side reactions during acylation chemistry, while the aromatic nitro group provides an electronically activated handle for reductive, oxidative, and substitution-based derivatization. As an amino acid building block and chiral intermediate, it can be incorporated into peptide sequences or converted into functional aromatic derivatives used in synthetic organic chemistry and biochemical research workflows.
1. Protected Amino Acid Synthesis
Cbz-3-Nitro-L-Phenylalanine is applied in protected amino acid synthesis and chiral intermediate preparation where an N-protected amino group is required for controlled peptide coupling chemistry. The Cbz carbamate protects the alpha-amino functionality during activation of the carboxyl group, while the meta-nitro substituted phenyl side chain remains intact for later functional group manipulation. Nitro-bearing aromatic side chains can be carried through coupling steps and then selectively transformed after deprotection, enabling staged synthesis of amino acid derivatives and peptidomimetic scaffolds. The L-stereocenter supports stereochemically consistent incorporation into growing peptide chains, aligning with synthetic strategies for protected amino acids used in fine chemical production and research-grade intermediate supply.
2. Peptide Synthesis
Cbz-3-Nitro-L-Phenylalanine is suitable for peptide synthesis workflows that require an N-protected, stereodefined amino acid building block with an aromatic functional handle. The Cbz-protected amine and carboxylic acid functionality enable standard peptide coupling approaches while minimizing side reactions from the amino group, and the aromatic nitro substituent can influence reactivity and solubility of the resulting peptide fragments. Post-coupling deprotection strategies can unmask the amine for sequential chain extension, while the nitro group can serve as a latent functionality for later reduction to an aniline or for other aromatic modifications. The resulting nitro-containing peptide analogs can be used as defined substrates or structural probes in peptide chemistry, supporting downstream derivative generation and structure-function studies.
3. Side-Chain Functionalization
Cbz-3-Nitro-L-Phenylalanine is employed for side-chain functionalization in synthetic organic chemistry where the meta-nitro aromatic group functions as a versatile transformation handle. The nitro substituent can undergo controlled reductive conversion to corresponding amino derivatives or can be leveraged for electrophilic aromatic substitution patterns that depend on the aromatic activation state, enabling access to multiple functionalized phenylalanine analogs. The Cbz-protected amino group allows orthogonal chemistry planning, separating manipulations of the aromatic nitro functionality from amino deprotection and subsequent coupling steps. The chiral alpha-carbon stereochemistry is retained through these transformations when appropriate conditions are used, providing stereochemically consistent intermediates for peptidomimetic construction, medicinal chemistry fragment elaboration, and process chemistry intermediate preparation.
4. Chemical Biology Probes
Cbz-3-Nitro-L-Phenylalanine is utilized in chemical biology research to generate aromatic nitro-containing amino acid derivatives that can serve as structural probes or reactive handles in biomolecule modification studies. The combination of an L-phenylalanine backbone and an electronically defined nitro group supports the preparation of labeled or modified peptide motifs where side-chain electronics and polarity are relevant to molecular recognition. The Cbz protection strategy enables incorporation into peptide sequences or peptide-like constructs while maintaining compatibility with sequential synthesis and controlled deprotection schedules. Downstream conversion of the nitro functionality can provide access to functional aromatic groups suitable for conjugation chemistry, enabling defined biomolecule modification workflows and analytical reference material generation.
5. SAR Studies
Cbz-3-Nitro-L-Phenylalanine is applied in structure-activity relationship studies and molecular design efforts that require systematic variation of aromatic side-chain electronics and functional group identity. The meta-nitro substituted phenyl ring introduces a defined electron-withdrawing substituent that can be retained during early scaffold assembly or transformed into alternative aromatic functionalities for comparative SAR panels. The protected amino acid format supports consistent peptide coupling and stereochemical control, allowing researchers to build libraries of peptide analogs or peptidomimetic fragments with matched stereochemistry. Nitro-to-amino or other aromatic conversions enable generation of closely related analogs differing primarily in side-chain functionality, supporting iterative SAR refinement in research and fine chemical synthesis programs.
1. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
4. Myotropic activity of allatostatins in tenebrionid beetles
5. Cationic cell-penetrating peptides are potent furin inhibitors
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More