In the intricate world of chemical synthesis, understanding the properties and applications of specialized compounds is crucial for researchers and industry professionals. Boc-L-3-Cyanophenylalanine, identified by its CAS number 131980-30-8, is a significant non-natural amino acid derivative widely used as a building block in peptide synthesis and related chemical research. This article provides a comprehensive overview of its key attributes, including its physical appearance, chemical characteristics, and primary uses.

Key Chemical and Physical Properties

Boc-L-3-Cyanophenylalanine is a derivative of the amino acid phenylalanine, featuring two critical modifications: a tert-butyloxycarbonyl (Boc) protecting group on the alpha-amino group and a cyano group attached to the meta position of the phenyl ring. These features dictate its behavior and utility:

  • Molecular Formula: C15H18N2O4
  • Molecular Weight: Approximately 290.31 g/mol
  • CAS Number: 131980-30-8
  • Physical Appearance: Typically described as a white to off-white solid or powder. This physical state is common for many protected amino acids used in synthesis.
  • Purity: Available from manufacturers and suppliers with high purity levels, often exceeding 97% or 98% (verified by HPLC), which is critical for reliable chemical reactions.
  • Solubility: Generally soluble in organic solvents commonly used in peptide synthesis, such as dimethylformamide (DMF) or dichloromethane (DCM), but less soluble in water.
  • Melting Point: Reports vary, but it generally falls within the range of 124-129°C, indicating a stable solid form.

The Boc group provides acid-labile protection, allowing for its facile removal under mild acidic conditions during peptide synthesis. The cyano group offers a polar functionality that can influence the solubility, electronic properties, and binding interactions of the final peptide molecule.

Primary Applications in Research and Industry

The primary application of Boc-L-3-Cyanophenylalanine lies in its role as a building block in peptide synthesis. This includes:

  • Peptide Chain Elongation: It is used in both solid-phase peptide synthesis (SPPS) and solution-phase synthesis to introduce a modified amino acid residue into a growing peptide chain. This is fundamental for creating synthetic peptides with specific biological functions or structural properties.
  • Drug Discovery and Development: As a non-natural amino acid, it enables the synthesis of novel peptides and peptidomimetics that can serve as potential drug candidates. Its unique side chain can offer advantages in stability, target affinity, or pharmacokinetic profiles.
  • Biochemical Research: Researchers may use it to study protein-ligand interactions, enzyme mechanisms, or to develop modified peptides for diagnostic or therapeutic purposes.

For professionals seeking to purchase Boc-L-3-Cyanophenylalanine, it is essential to source from reputable manufacturers and suppliers who can guarantee the specified quality and purity. Considering factors such as product appearance, purity levels, CAS number, and availability from reliable sources will ensure successful outcomes in research and synthetic applications.