O-Benzyl-D-alanine toluene-p-sulphonate
O-Benzyl-D-alanine toluene-p-sulphonate, identified by CAS number 41036-32-2, is a specialized chemical derivative of the non-proteogenic amino acid D-alanine. This compound exists as a p-toluenesulfonate salt of the benzyl ester, a configuration that enhances its stability and solubility in organic solvents compared to the free base form. As a chiral building block, it plays a critical role in the synthesis of complex organic molecules, particularly where the D-configuration of the alanine residue is required to impart specific biological or structural properties. The benzyl ester group serves as a robust protecting group for the carboxylic acid moiety, allowing for selective reactions at the amino terminus or other functional sites during multi-step synthesis. In industrial and research settings, this material is valued for its high purity and predictable reactivity, facilitating the construction of peptides, peptidomimetics, and various pharmaceutical intermediates. Proper handling involves standard laboratory protocols for organic salts, ensuring protection from moisture to maintain its integrity as a high-quality reagent for precision chemical manufacturing.
• Peptide Synthesis and Chain Elongation: This compound serves as a vital intermediate in the synthesis of peptides and peptidomimetics. By utilizing the benzyl ester as a C-terminal protecting group, chemists can perform selective coupling reactions at the N-terminus. The D-alanine configuration is particularly useful for creating D-amino acid-containing peptides, which are often more resistant to enzymatic degradation by proteases than their L-counterparts, making them essential in the development of long-acting therapeutic agents and biochemical probes.
• Medicinal Chemistry and Drug Discovery: CAS 41036-32-2 is frequently employed in the design and synthesis of diverse pharmaceutical candidates. It acts as a chiral scaffold for producing enzyme inhibitors, receptor ligands, and other biologically active molecules. The tosylate salt form provides a stable, crystalline material that is easy to handle and dispense during the early stages of drug discovery, ensuring consistent stoichiometry in high-throughput screening libraries and lead optimization studies.
• Asymmetric Synthesis and Chiral Building Blocks: Beyond peptide chemistry, this material is utilized as a chiral auxiliary or building block in general organic synthesis. Its defined stereochemistry allows for the introduction of the D-alanine moiety into non-peptidic frameworks, supporting the construction of complex natural products and fine chemicals where precise spatial orientation is required for functional efficacy.
Product Name: O-Benzyl-D-alanine toluene-p-sulphonate
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