Product Description:
BOC-Ala-OtBu, with the CAS number 58177-77-8, is a protected derivative of the amino acid L-alanine. Its chemical structure features two orthogonal protecting groups: the tert-butoxycarbonyl (Boc) group on the amine nitrogen and the tert-butyl (OtBu) ester on the carboxylic acid. This dual protection renders the molecule stable under a wide range of reaction conditions, making it a versatile and crucial building block.
This compound is primarily employed in the field of peptide synthesis, particularly in solid-phase peptide synthesis (SPPS) and solution-phase methods. The Boc group is a standard amine-protecting group that can be selectively removed under acidic conditions (e.g., with trifluoroacetic acid) without affecting the tert-butyl ester. Conversely, the OtBu ester can be cleaved under strong acidic conditions (e.g., with hydrogen fluoride or trifluoromethanesulfonic acid) while the Boc group remains intact under basic conditions. This orthogonality allows for the sequential and controlled assembly of complex peptide chains.
As a derivative of L-alanine, a proteinogenic amino acid, BOC-Ala-OtBu is fundamental for introducing alanine residues into synthetic peptides and peptidomimetics. These synthetic targets are essential in pharmaceutical research for drug discovery, the development of bioactive probes, and the study of protein-protein interactions. Its high purity and reliable deprotection protocols make it a staple reagent in both academic and industrial laboratories focused on medicinal chemistry and biochemistry.