3-Cyano-L-Phenylalanine is a non-proteinogenic, aromatic amino acid derivative featuring an L-configuration at the alpha carbon and a benzyl side chain bearing a nitrile substituent at the meta position relative to the benzylic carbon. The molecule contains a free alpha-amino group and a free carboxyl group, while the side chain nitrile provides a strongly electron-withdrawing functional handle that can participate in specific binding interactions and offers a chemically stable polarity element for structure-activity and labeling studies. It is used as a substrate or building block in peptide and amino-acid derivative synthesis to introduce a cyano-functional aromatic residue for conformational, electronic, and analytical property modulation in chemical biology and materials research.
3-Cyano-L-Phenylalanine is a cyano-substituted phenylalanine building block featuring the L-configuration and a nitrile side chain that functions as a chemically stable, electronically distinctive handle for downstream synthetic and analytical workflows. In peptide and peptidomimetic development, the cyano group provides a robust substituent that can be used to tune polarity and to support structure-property studies without introducing strongly reactive functionality. As a research-grade amino acid, it is commonly selected when a defined aromatic/cyano motif is required for labeling, affinity/interaction studies, or medicinal chemistry intermediate preparation.
1. Peptidomimetic Building Blocks
3-Cyano-L-Phenylalanine is used by peptide and peptidomimetic researchers to introduce a defined aromatic nitrile motif into short peptide analogs and SAR-focused analog series. The L-stereochemistry supports consistent incorporation into peptide-like structures during custom peptide synthesis, while the nitrile side chain offers a stable substituent that can influence local electronics and hydrogen-bonding patterns compared with unsubstituted phenylalanine. Medicinal chemistry groups often rely on this building block when designing constrained analogs where a persistent, non-hydrolyzable side-chain functionality is advantageous for maintaining structural integrity across lead-optimization campaigns.
2. Medicinal Chemistry Intermediates
3-Cyano-L-Phenylalanine is frequently employed in pharmaceutical intermediate development as a structurally defined precursor for downstream transformations that retain the amino acid backbone while converting the nitrile-bearing aromatic side chain into other functional motifs. Process and research chemists value the compound as a "ready-to-derive" chiral amino acid scaffold for preparing cyano-derived intermediates used in lead diversification, scaffold hopping, and late-stage functional group interconversion strategies. Because the nitrile is a chemically robust group, it can serve as a durable handle during multi-step synthesis planning where side-chain stability and predictable reactivity are important.
3. Isotope-Independent Analytical Standards
3-Cyano-L-Phenylalanine is used to support analytical method development and calibration workflows where a nitrile-bearing phenylalanine analog is required as a reference material. LC-MS and related analytical platforms often benefit from having an authentic, structurally matched standard to verify retention behavior and mass spectral features for amino acid profiling, impurity monitoring, or characterization of peptide/peptidomimetic intermediates. Analytical chemistry teams also use this compound when building internal quality controls for synthetic batches that include cyano-substituted aromatic amino acid derivatives, helping ensure consistent identification and quantitation during development and scale-up studies.
2. Emerging applications of nanotechnology for diagnosis and therapy of disease: a review
3. Myotropic activity of allatostatins in tenebrionid beetles
4. Low bone turnover and low BMD in Down syndrome: effect of intermittent PTH treatment
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