Alloc-L-Lys(Fmoc)-OH

Product Overview

Alloc-L-Lys(Fmoc)-OH is a highly specialized protected amino acid derivative essential for modern solid-phase peptide synthesis (SPPS). This compound features a unique orthogonal protection scheme, utilizing an Allyloxycarbonyl (Alloc) group on the alpha-amino position and a 9-Fluorenylmethyloxycarbonyl (Fmoc) group on the epsilon-amino side chain of L-Lysine. This specific configuration allows chemists to selectively deprotect either the backbone or the side chain under distinct conditions, facilitating the construction of complex peptide architectures, cyclic peptides, and branched structures without compromising the integrity of the remaining molecule.

Chemical Properties And Structure

The molecular formula C25H28N2O6 reflects a robust structure designed for stability during rigorous synthesis cycles. The Alloc group is removable under mild palladium-catalyzed conditions, which are orthogonal to the base-labile Fmoc group. This orthogonality is critical for multi-step synthesis where specific functional groups must be exposed sequentially. The compound exhibits excellent solubility in common organic solvents such as DMF and DCM, ensuring efficient coupling reactions. Its high molecular weight of 452.50 g/mol is consistent with the dual protection strategy, providing the necessary steric and electronic properties for high-fidelity peptide assembly.

Industrial Applications

This building block is primarily utilized in the pharmaceutical and biotechnology sectors for the development of therapeutic peptides and diagnostic agents. It is particularly valuable in the synthesis of peptides requiring side-chain modifications or cyclization via the lysine epsilon-amino group. Researchers employ this reagent when standard Fmoc protection on the alpha-amine is not suitable for the specific synthetic route. Common applications include the production of peptide hormones, antimicrobial peptides, and custom research compounds where precise control over protecting group removal is paramount for yield and purity.

Quality Specifications

Our manufacturing process adheres to strict quality control standards to ensure batch-to-batch consistency. Each lot undergoes comprehensive analysis using High-Performance Liquid Chromatography (HPLC) and other analytical techniques. The following table outlines the key quality parameters verified for this product:

Storage And Handling

To maintain optimal stability and reactivity, Alloc-L-Lys(Fmoc)-OH should be stored in a cool, dry place away from direct light and moisture. It is recommended to keep the container tightly sealed under inert gas when not in use to prevent degradation of the protecting groups. Proper handling procedures include using appropriate personal protective equipment during weighing and transfer. When stored correctly at recommended temperatures, this product maintains its specified purity and physical characteristics for extended periods, ensuring reliability for long-term research projects and production scales.