2-Cyano-DL-Phenylalanine is a non-natural amino acid derivative featuring a phenylalanine backbone bearing a cyano substituent at the 2-position of the α-carbon (β-phenyl side chain) and existing as a DL stereochemical mixture. The molecule contains a free amino group and a free carboxyl group along with a nitrile side-chain functionality that provides a strongly electron-withdrawing handle for chemical characterization and derivatization. As a chemically defined phenylalanine analogue, it is used in peptide and amino-acid analogue synthesis and in structure-activity or labeling studies where the cyano-modified stereochemical mixture and nitrile group are relevant for analytical method development and comparative biochemical studies.
CAT No: CP11703
2-Cyano-DL-Phenylalanine is a cyano-substituted phenylalanine analog supplied as a DL mixture, providing both stereochemical forms for downstream synthesis and method development. The side-chain nitrile introduces a chemically robust functional handle that can be retained through peptide- and heterocycle-related workflows, while the amino acid backbone supports conversion into protected derivatives and activated intermediates. This reagent is frequently selected when a stable, non-hydrolyzable nitrile group is required to tune reactivity, polarity, or downstream derivatization without relying on side-chain oxidation or reduction.
1. Peptidomimetic Building Blocks
2-Cyano-DL-Phenylalanine supports the preparation of peptide-like structures and peptidomimetic scaffolds where a nitrile-bearing aromatic side chain is used to modulate shape and electronic character. Medicinal chemistry and chemical biology groups commonly incorporate this amino acid analog into custom peptide libraries and structure-activity relationship (SAR) studies, particularly when a stable nitrile substituent is desired as a conformationally and chemically persistent feature. Researchers also use it as a starting material for protected amino acid derivatives that can be assembled into short sequences for binding studies, protease substrate profiling, or inhibitor/ligand optimization workflows where conventional phenylalanine analogs would not provide the same side-chain functionality.
2. Pharmaceutical Intermediate Synthesis
2-Cyano-DL-Phenylalanine is widely used as a chiral-agnostic amino acid intermediate for routes that require a nitrile-functional aromatic side chain in the target scaffold. Process development and fine-chemical manufacturers select the DL form when separation is unnecessary for the next transformation step or when downstream resolution will be performed at a later stage. The nitrile group enables further synthetic diversification into amide, amidine, or other nitrogen-containing motifs under standard intermediate-manufacturing conditions, making this building block valuable for producing heterocycle precursors and specialty intermediates used across medicinal chemistry programs. Its amino acid backbone further supports conversion to activated forms for coupling into more complex structures.
3. Nitrile-Handle Derivatization Studies
2-Cyano-DL-Phenylalanine is frequently employed in chemical biology and analytical chemistry workflows that require a stable nitrile "handle" for controlled derivatization. Laboratories use the nitrile functionality to generate downstream derivatives for assay development, reference material preparation, and comparative studies of how a nitrile substituent influences physicochemical properties such as polarity and chromatographic behavior. Because the amino acid framework can be transformed into protected or activated derivatives, it is also used to benchmark labeling or coupling strategies where robust functional-group compatibility is needed, especially when side-chain nitriles must survive multiple synthetic or sample-preparation steps without rapid hydrolysis.
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