Boc-Phenylalanine

Updated: 2026-08-02

Overview

Boc-L-phenylalanine is a tert-butoxycarbonyl (Boc) protected derivative of the essential amino acid L-phenylalanine. It serves as a crucial building block in solid-phase peptide synthesis (SPPS) and other organic synthetic processes. The Boc group protects the amino functionality during peptide chain assembly, enabling selective deprotection under mild acidic conditions. This compound is widely utilized in pharmaceutical research for constructing peptide-based drugs and bioactive molecules. Its chiral purity and stability make it a preferred choice for controlled synthesis. The global demand for Boc-L-phenylalanine has grown steadily due to increasing applications in drug discovery and biotechnology.

Physical and Chemical Properties

Boc-L-phenylalanine presents as a white crystalline solid with a molecular weight of 265.31 g/mol. It exhibits moderate solubility in polar organic solvents like dimethylformamide (DMF) and dimethyl sulfoxide (DMSO), but limited solubility in water. The melting point typically ranges between 85-88°C, though this may vary slightly depending on purity and crystalline form. The compound demonstrates stability under standard storage conditions but may degrade upon prolonged exposure to moisture or strong acids/bases. Its chiral center at the α-carbon maintains the L-configuration, critical for biological activity in peptide synthesis. The Boc protecting group is stable to base but can be cleaved by trifluoroacetic acid (TFA) or hydrogen chloride in organic solvents.

Main Applications

In peptide synthesis, Boc-L-phenylalanine serves as a key intermediate for introducing phenylalanine residues while preventing unwanted side reactions. Pharmaceutical researchers employ it in developing peptide hormones, enzyme inhibitors, and receptor-targeting compounds. The compound's aromatic side chain contributes to hydrophobic interactions in peptide structures. Beyond pharmaceuticals, this protected amino acid finds use in biochemical research for studying protein-protein interactions and enzyme mechanisms. Some specialty chemical manufacturers incorporate it into custom peptide sequences for diagnostic reagents and research tools. The compound's consistent quality and reliable reactivity profile make it valuable for high-throughput combinatorial chemistry applications.

Safety and Storage

While Boc-L-phenylalanine is not classified as highly hazardous, appropriate safety measures should be observed. Laboratory personnel should wear nitrile gloves, safety goggles, and protective clothing when handling the powder to prevent skin/eye contact. Inhalation of dust should be avoided through use of fume hoods or particulate respirators. The material should be stored in tightly sealed containers under cool (2-8°C), dry conditions, protected from light and moisture. Under proper storage, the compound typically maintains stability for several years. Opened containers should be flushed with inert gas before resealing to minimize moisture absorption and oxidative degradation.

B2B Procurement Guide

When sourcing Boc-L-phenylalanine commercially, buyers should prioritize suppliers with ISO-certified manufacturing facilities and comprehensive analytical documentation. Key specifications to verify include: HPLC purity (typically ≥98%), enantiomeric excess (≥99%), residual solvent levels, and endotoxin content for sensitive applications. Bulk purchasers should request certificates of analysis (CoA) for each batch and consider arranging for third-party testing when establishing new supplier relationships. Lead times may vary from 2-8 weeks depending on quantity and customization requirements. Many suppliers offer technical support for specialized applications, which can be valuable for process development teams.