2-Cyano-D-Phenylalanine is a non-proteinogenic, aromatic amino acid derivative bearing a phenyl side chain substituted with a cyano group at the 2-position relative to the alpha carbon, and it contains both an amino group and a carboxyl group as the free amino acid framework. The "D" designation specifies the stereochemical configuration at the alpha carbon, while the nitrile functionality provides a strongly electron-withdrawing handle that can influence side-chain polarity and participate in specific chemical interactions during synthesis or analytical characterization. In peptide chemistry and chemical biology, it is used as a structurally modified amino acid building block to introduce a nitrile-bearing aromatic residue for structure-activity studies, labeling strategies, and the preparation of peptides and peptide analogues with altered physicochemical properties.
CAT No: CP11702
CAS No:263396-41-4
Synonyms/Alias:263396-41-4;D-2-Cyanophenylalanine;(R)-2-Amino-3-(2-cyanophenyl)propanoicacid;2-Cyano-D-phenylalanine;D-2-Cyanophe;(2R)-2-amino-3-(2-cyanophenyl)propanoicAcid;D-2-Cyanophenylalarine;D-Phe(2-CN)-OH;SCHEMBL2030783;CTK8E3999;MolPort-003-793-969;ZINC2385768;AKOS006345216;AC-5871;AM82757;VC30896;AJ-35172;AK109493;AN-10521;BC227269;KB-49526;M236;AB0015130;RT-007716;TL8002101
2-Cyano-D-Phenylalanine is a D-configured phenylalanine analog bearing a cyano substituent on the aromatic ring, making it a rigid, electron-withdrawing side-chain variant used as a non-proteinogenic amino acid building block in chemical biology and medicinal chemistry workflows. Its distinctive nitrile functionality supports downstream derivatization and structure-property studies, while the D-stereochemistry helps researchers probe stereochemical effects in peptide and peptidomimetic design. Because it is not a canonical proteinogenic residue, it is typically employed to introduce controlled chemical functionality into synthetic peptides and related research materials.
1. Peptidomimetic Building Blocks
2-Cyano-D-Phenylalanine is used by peptide chemists to incorporate a non-natural, stereochemically defined aromatic residue into peptidomimetic scaffolds and modified peptide analogs. Researchers commonly select this cyano-substituted phenylalanine variant to tune local electronics, aromatic character, and conformational preferences in structure-activity relationship (SAR) studies, particularly when stereochemistry (D-configuration) is used as a design variable. In custom peptide synthesis workflows, it serves as a defined amino acid building block for generating analog series where the nitrile-bearing aromatic side chain provides a chemically distinct handle and a consistent residue identity for downstream characterization.
2. Structure-Activity Relationship Studies
2-Cyano-D-Phenylalanine supports medicinal chemistry programs that evaluate how aromatic ring substitution and D-amino acid stereochemistry influence binding-site interactions and overall molecular behavior in synthetic lead optimization. By using a residue that contains an electron-withdrawing nitrile group, researchers can systematically compare analogs that differ in side-chain electronic properties while keeping the backbone and stereochemical context controlled. This makes the compound a practical tool for SAR campaigns, where defined incorporation of a non-natural residue helps separate effects from general hydrophobicity and supports more interpretable structure-property trends across peptide-like candidates.
3. Chemical Biology Probe Design
2-Cyano-D-Phenylalanine is applied in chemical biology for constructing peptide-based probes and affinity reagents that require a non-proteinogenic aromatic residue with a nitrile substituent for controlled chemical derivatization. The cyano group provides a stable, chemically informative motif that can be leveraged during probe development to introduce or modulate functional features without relying on canonical amino acid side chains. Teams developing labeling-ready peptide constructs use this building block to maintain stereochemical definition while enabling consistent probe synthesis and subsequent analytical verification of residue identity in complex probe formats.
4. Pharmaceutical Intermediate Development
2-Cyano-D-Phenylalanine is also used as a defined intermediate building block in the preparation of specialized amino acid derivatives and peptide-related intermediates for research and industrial development. Process development groups and specialty chemical manufacturers incorporate this cyano-bearing D-amino acid into downstream synthetic sequences where the nitrile functionality and stereochemical integrity are required in the target intermediate. This positioning is particularly relevant when the final material depends on maintaining a specific substituted aromatic side chain identity for later coupling, derivatization, or incorporation into larger chemical frameworks.
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