Fmoc-2-Cyano-D-Phenylalanine is an Fmoc-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing a 2-cyano substituent on the alpha-carbon and a benzyl side chain with a phenyl group. The molecule contains a free carboxyl group and an amino functionality masked as an Fmoc carbamate, while the cyano group provides a strongly electron-withdrawing nitrile handle that can influence polarity and hydrogen-bonding behavior during peptide assembly and subsequent transformations. In peptide chemistry, it is used as a protected building block for introducing the 2-cyano modified phenylalanine residue into peptides via stepwise coupling strategies, and the nitrile functionality is commonly leveraged for structure-activity studies, chemical labeling, or downstream derivatization to generate further amino acid and peptide derivatives.
CAT No: CP11707
Fmoc-2-Cyano-D-Phenylalanine is an Fmoc-protected D-phenylalanine derivative bearing a side-chain cyano substituent at the alpha-position relative to the aromatic ring (2-cyano functionality). The molecule combines a chiral amino acid stereocenter with an Fmoc carbamate that supports solid-phase peptide synthesis, while the cyano group introduces a strongly electron-withdrawing nitrile handle for further functional group transformation. The aromatic phenyl ring and the nitrile together modulate polarity and can influence conformational preferences and hydrogen-bonding patterns in peptide backbones and peptidomimetics. As an amino acid building block, it is engineered for controlled peptide coupling after Fmoc removal, with the nitrile remaining stable under many standard peptide-protection conditions and serving as a downstream synthetic handle.
1. Peptide Synthesis
Fmoc-2-Cyano-D-Phenylalanine is used in peptide building block preparation for Fmoc-based peptide synthesis where the Fmoc group enables orthogonal N-deprotection and subsequent amide bond formation at the alpha-amino functionality. The D-configuration provides stereochemical control for incorporating D-amino acid residues into peptide sequences, supporting studies of protease resistance and backbone stereochemical effects. The side-chain nitrile can remain intact through peptide coupling and deprotection cycles, allowing nitrile-bearing peptide analogs to be generated for structure-activity relationship studies and binding assays. Downstream, the nitrile-functionalized residue can be converted into amines, amides, or heterocycles, enabling late-stage diversification of peptide scaffolds from a single chiral precursor.
2. Peptidomimetics Design
Fmoc-2-Cyano-D-Phenylalanine supports peptidomimetic construction by providing a chiral, aromatic amino acid framework with a nitrile substituent that can act as a polarity modulator and a synthetic convergence point. The nitrile group enables subsequent derivatization to generate amide or amidine-like functionalities, or to feed heterocycle-forming routes while maintaining the stereochemical information encoded by the D-phenylalanine center. The Fmoc-protected amine allows incorporation into short peptide-like sequences or constrained scaffolds where side-chain electronics and dipole character influence molecular recognition. The resulting nitrile-containing peptidomimetics can be used as chemical probes and SAR intermediates in medicinal chemistry workflows focused on backbone and side-chain tuning.
3. Side-Chain Functionalization
Fmoc-2-Cyano-D-Phenylalanine is applied as an amino acid derivatization intermediate for introducing a nitrile functional handle into chiral molecules that require controlled post-coupling transformations. The cyano group provides a robust electrophilic site for conversion into nucleophilic nitrogen-containing motifs under appropriate conditions, enabling access to substituted amines, carboxamide analogs, and nitrile-derived heterocycles. The protected amino acid form allows nitrile-bearing intermediates to be assembled into peptides or protected fragments before functional group conversion, supporting modular synthesis strategies. Downstream functionalization of the nitrile-bearing residue supports generation of diversified libraries and process-oriented intermediate preparation for fine chemical synthesis.
4. Chemical Biology Probes
Fmoc-2-Cyano-D-Phenylalanine is suitable for chemical biology research where D-amino acid incorporation and nitrile-bearing side chains help create stable peptide analogs for target engagement and pathway mapping. The Fmoc group supports controlled assembly of labeled or affinity-tagged constructs, while the D-stereochemistry can reduce susceptibility to proteolysis and preserve probe integrity during experimental timeframes. The nitrile functionality can be used as a handle for subsequent conjugation-adjacent transformations, including conversion to reactive nitrogen functionalities that enable attachment to biomolecular partners. The product therefore functions as a chiral amino acid intermediate for generating peptide-based probes, mechanistic tool compounds, and biochemical research reagents that rely on stereodefined backbone chemistry.
5. Pharmaceutical Intermediate Preparation
Fmoc-2-Cyano-D-Phenylalanine is relevant to pharmaceutical intermediate preparation and process chemistry as a protected amino acid building block that can be scaled into nitrile-containing chiral fragments used in medicinal chemistry programs. The Fmoc-protected N-terminus supports standardized peptide coupling operations during route development, while the D-configuration supports stereochemically defined analog synthesis for SAR studies and scaffold refinement. The nitrile group serves as a manufacturing-compatible functional handle that can be carried through protected steps and then converted into downstream functional groups required for active-ingredient-like motifs. The compound's structure aligns with industrial workflows that require chiral amino acid intermediates capable of supporting both peptide-derived and non-peptidic derivative synthesis from a common intermediate.
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