2-Cyano-L-Phenylalanine is an L-configured, non-proteinogenic phenylalanine derivative in which the side chain bears a cyano substituent at the 2-position relative to the α-amino acid backbone. The molecule contains an α-amino group and a carboxyl group along with a nitrile functional group on the aromatic side chain, providing a strongly electron-withdrawing handle that can influence hydrogen bonding patterns and side-chain polarity in peptide contexts. It is used in peptide chemistry and chemical biology as a substituted amino acid for structure-activity studies, incorporation into synthetic peptides to probe effects of nitrile-bearing aromatic residues, and analytical method development where the distinct nitrile functionality supports targeted detection or derivatization.
CAT No: CP11701
CAS No:263396-42-5
Synonyms/Alias:263396-42-5;L-2-Cyanophenylalanine;(S)-2-Amino-3-(2-cyanophenyl)propanoicacid;2-Cyano-L-Phenylalanine;(2S)-2-amino-3-(2-cyanophenyl)propanoicacid;L-2-Cyanophe;D-2-Cyanophenylalarine;L-2-Cyanophenylalarine;Phenylalanine,2-cyano-;L-Phe(2-CN)-OH;AC1MC53J;SCHEMBL42647;CTK1A1445;MolPort-003-793-968;ZINC2385773;ANW-60600;SBB063700;AC-5870;AL232-1;AM82756;AJ-35176;AK-89322;AM000148;AN-10520;KB-50219
2-Cyano-L-Phenylalanine is a non-proteinogenic L-amino acid analog bearing a cyano substituent on the aromatic ring, which makes it a useful electrophile handle and a distinctive aromatic motif for downstream synthetic and structure-driven studies. Its amino acid functionality supports incorporation into peptide-like frameworks and derivatization workflows, while the aromatic nitrile provides a chemically robust site for further functional transformation and analytical tagging. Researchers commonly select this building block when they need a phenylalanine-derived scaffold with a defined electronic/steric signature that is not found in the standard proteinogenic amino acids.
1. Peptide Building Block Use
2-Cyano-L-Phenylalanine is used as a specialized amino acid building block for custom peptide synthesis where a phenylalanine-like residue with an aromatic nitrile is required for SAR (structure-activity relationship) studies, probe generation, or mechanistic peptide analogs. Peptide chemists incorporate this residue into solution-phase or solid-phase peptide assemblies to introduce a non-natural aromatic functionality without changing the overall amino acid backbone identity. The nitrile-bearing phenyl side chain is particularly valuable for creating peptides with a chemically addressable substituent that can be retained for stability or converted downstream into alternative functional groups for iterative medicinal chemistry campaigns.
2. Medicinal Chemistry Intermediate
2-Cyano-L-Phenylalanine serves as a practical pharmaceutical intermediate for medicinal chemistry programs that require access to nitrile-functionalized aromatic motifs derived from an amino acid scaffold. Process and synthesis teams often use it to build libraries of substituted analogs where the aromatic cyano group is leveraged as a stable, structurally informative substituent and as a precursor for further derivatization. Because the compound maintains the amino acid core, it can be carried through multi-step sequences that convert the side-chain nitrile into new chemical features while preserving stereochemical definition from the L-configuration.
3. Chemical Biology Probe Design
2-Cyano-L-Phenylalanine is applied in chemical biology workflows to create site-specific aromatic nitrile-containing probes and labeling reagents where a non-natural phenylalanine analog is needed. Researchers use this building block to generate peptide-based or amino-acid-derived probes that contain a defined, non-native aromatic handle for subsequent conjugation or transformation steps, enabling controlled probe architectures for studying binding interactions, substrate recognition, or biomolecular labeling strategies. The cyano substituent provides an orthogonal chemical feature that can be used to tune probe properties and to support downstream functionalization while keeping the probe's amino acid-derived geometry consistent with phenylalanine-based designs.
4. Analytical Reference Standards
2-Cyano-L-Phenylalanine is also used for analytical reference and method-development work where a nitrile-substituted phenylalanine analog is required as a calibration component, internal standard candidate, or structural comparator. LC-MS and related analytical platforms benefit from having well-defined, stereochemically specified amino acid standards that reflect the exact mass and fragmentation behavior of the nitrile-bearing aromatic side chain. In practice, analytical teams employ it to validate chromatographic separation, confirm identity in complex matrices, and support quantitative workflows that track nitrile-containing amino acid derivatives during synthetic development or stability studies.
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