The utility of Boc-L-2-Cyanophenylalanine in modern chemical synthesis, particularly in peptide chemistry and drug discovery, stems from its distinct chemical properties and carefully designed synthesis routes. As a protected, non-natural amino acid, understanding its molecular structure and reactivity is key for researchers aiming to leverage its full potential.

Boc-L-2-Cyanophenylalanine, identified by CAS number 216312-53-7, is characterized by its molecular formula C15H18N2O4 and a molecular weight of approximately 290.31 g/mol. The defining features are the tert-butyloxycarbonyl (Boc) protecting group on the alpha-amino nitrogen and a cyano (-CN) group substituted at the ortho (2-) position of the phenyl ring of the phenylalanine side chain. This specific arrangement imparts unique electronic and steric properties.

The Boc group is a widely used amine protecting group in solid-phase peptide synthesis (SPPS) and solution-phase synthesis. Its stability under various reaction conditions, coupled with its facile removal under mild acidic conditions (e.g., trifluoroacetic acid), makes it ideal for stepwise peptide chain elongation. The presence of the cyano group on the aromatic ring influences the electron density distribution and can affect intermolecular interactions, making it a valuable modification for modulating peptide properties.

Synthesizing Boc-L-2-Cyanophenylalanine typically involves derivatizing phenylalanine or a precursor molecule. The process usually begins with the introduction of the cyano group onto the phenyl ring, often through electrophilic aromatic substitution or cross-coupling reactions with appropriate reagents. Following this, the alpha-amino group of the resulting 2-cyanophenylalanine is protected with the Boc group, commonly using di-tert-butyl dicarbonate (Boc anhydride) in the presence of a base. Careful control of stereochemistry is crucial to ensure the L-configuration is maintained, which is vital for biological activity in subsequent peptide applications.

For researchers and procurement specialists, specifying the purity and isomerism of Boc-L-2-Cyanophenylalanine is critical. Manufacturers who can demonstrate high enantiomeric purity (ee%) alongside chemical purity (e.g., ≥99% by HPLC) are preferred. Understanding the synthesis pathway helps in appreciating the quality and potential impurities associated with the product.

When you buy Boc-L-2-Cyanophenylalanine, partnering with a reliable Boc-L-2-Cyanophenylalanine manufacturer ensures you receive a product that has undergone rigorous synthesis and purification. This attention to detail in chemical properties and synthesis underpins its successful application in demanding research areas. We are committed to providing scientists with high-quality Boc-L-2-Cyanophenylalanine that meets the stringent demands of modern chemical research and development.