Exploring the Chemistry of 4-[(2,4-Dimethoxyphenyl)(Fmoc-amino)methyl]phenoxyacetic Acid
The field of organic synthesis, particularly as it pertains to peptide chemistry, relies on a toolkit of specialized reagents, each with unique structural features and functional roles. Among these, linkers that facilitate peptide attachment to solid supports during Solid-Phase Peptide Synthesis (SPPS) are of paramount importance. This article explores the chemistry of 4-[(2,4-Dimethoxyphenyl)(Fmoc-amino)methyl]phenoxyacetic acid (CAS 145069-56-3), a compound that has proven invaluable to peptide chemists. Understanding its structure, properties, and applications is essential for researchers looking to buy high-quality materials from a trusted supplier.
The molecular structure of 4-[(2,4-Dimethoxyphenyl)(Fmoc-amino)methyl]phenoxyacetic acid is a testament to the precision required in modern chemical synthesis. It comprises several key functional groups: an Fmoc-protected amino group, a dimethoxyphenyl moiety, and a phenoxyacetic acid tail. The Fmoc group serves as the standard protecting group for the alpha-amino function of amino acids in SPPS. The dimethoxyphenyl unit, attached via a chiral center, and the phenoxyacetic acid tail connected to the central methylene group, are integral to the linker's attachment to the resin and its subsequent cleavage characteristics. This detailed chemical architecture is what makes it an attractive building block to purchase.
The typical appearance of this compound, as described by manufacturers, is a white to off-white powder, indicative of its purity. With a molecular weight of approximately 539.58 g/mol and the chemical formula C32H29NO7, it is a moderately complex organic molecule. Its primary role is in Fmoc-based SPPS, where it is attached to a suitable resin. The phenoxyacetic acid portion of the molecule typically reacts with functional groups on the resin, such as amine-functionalized resins, to create a stable linkage.
Researchers often choose this linker due to its ability to facilitate efficient coupling reactions and its compatibility with standard Fmoc deprotection and cleavage protocols. The specific electronic and steric properties conferred by the dimethoxyphenyl group can influence the reactivity and stability of the linker-peptide bond. When considering the price of such a specialized reagent, it reflects the intricate synthesis process and the guaranteed high purity (often 99% HPLC) that a reputable manufacturer provides.
Beyond its primary use in peptide synthesis, this compound can also serve as a versatile intermediate in other areas of organic synthesis and medicinal chemistry. Its multiple functional groups offer opportunities for further chemical modifications, making it a useful building block for constructing more complex molecular architectures. For laboratories involved in custom synthesis or drug discovery programs, securing a reliable supplier for such intermediates is crucial for project continuity.
In conclusion, understanding the chemical intricacies of reagents like 4-[(2,4-Dimethoxyphenyl)(Fmoc-amino)methyl]phenoxyacetic acid (CAS 145069-56-3) is fundamental for successful peptide synthesis and broader organic chemistry applications. Its carefully designed structure ensures its efficacy in Fmoc SPPS. We encourage researchers and procurement professionals to inquire about this product and consider our commitment as a quality-focused manufacturer and supplier for your laboratory's needs.
Perspectives & Insights
Logic Thinker AI
“The Fmoc group serves as the standard protecting group for the alpha-amino function of amino acids in SPPS.”
Molecule Spark 2025
“The dimethoxyphenyl unit, attached via a chiral center, and the phenoxyacetic acid tail connected to the central methylene group, are integral to the linker's attachment to the resin and its subsequent cleavage characteristics.”
Alpha Pioneer 01
“This detailed chemical architecture is what makes it an attractive building block to purchase.”