Boc-2-Cyano-L-Phenylalanine is a Boc-protected amino acid derivative of L-phenylalanine bearing a nitrile substituent at the 2-position of the side chain. The molecule contains a carbamate-protected α-amino group (Boc) and a free carboxylic acid, with the 2-cyano functionality providing a polar, electron-withdrawing nitrile handle that can influence peptide coupling and subsequent chemical transformations. It is used in peptide chemistry as a protected, structurally modified building block for incorporating a cyano-substituted phenylalanine residue into peptide chains for structure-activity studies, chemical biology labeling strategies, and preparation of more complex amino acid derivatives.
CAT No: CP11704
Boc-2-Cyano-L-Phenylalanine is a Boc-protected, L-configured phenylalanine derivative bearing a side-chain 2-cyano substituent, making it a structurally distinctive amino acid building block for peptide and peptidomimetic synthesis. The cyano functionality provides a strong nitrile handle that can be leveraged for downstream chemical modification or for introducing polarity and conformational constraints in synthetic sequences. As a protected amino acid, it is typically handled as a synthesis-ready intermediate in workflows where the N-terminus is protected for controlled coupling chemistry.
1. Peptide Building Block Use
Boc-2-Cyano-L-Phenylalanine is used by peptide synthesis groups to incorporate a nitrile-bearing phenylalanine analog into protected peptide sequences, enabling access to peptides with tailored side-chain electronics and polarity. Researchers developing peptidomimetics and structure-property libraries often select this building block when they want a phenylalanine-derived residue that differs from standard Phe at the 2-position, while retaining a Boc-protected amino functionality for routine coupling and subsequent segment assembly. The Boc protection supports compatibility with common protected-amino-acid handling practices used in custom peptide manufacturing and academic peptide chemistry.
2. Peptidomimetic SAR Development
Boc-2-Cyano-L-Phenylalanine supports medicinal chemistry and chemical biology teams building peptidomimetic scaffolds for structure-activity relationship studies, where side-chain modification is used to tune physicochemical behavior and interaction patterns without changing the peptide backbone framework. The nitrile group can serve as a functional motif to probe how increased dipole character and altered hydrogen-bonding patterns influence binding or stability trends in synthetic series. In practice, the reagent is commonly deployed as a defined, stereochemically consistent amino acid unit within analog panels, helping teams generate reproducible SAR datasets during lead optimization chemistry.
3. Nitrile-Functional Intermediate Synthesis
Boc-2-Cyano-L-Phenylalanine is also employed as a pharmaceutical intermediate building block when a protected amino acid framework is required alongside a nitrile-bearing aromatic side chain. Process development chemists and intermediate manufacturers use it to access downstream derivatives where the nitrile group is retained as a reactive or convertible functional element during later transformations, while the Boc group provides protection for the amine during multi-step synthesis. This makes the compound a practical choice for constructing specialty amino acid derivatives that are subsequently elaborated into more complex chemical entities for research-grade material production.
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