BASIC STUDY OF THE AMINO ACID RESIDUE IN PROTEIN. THE ROLE OF HYDROCARBON GROUPS IN ENANTIOMER-DIFFERENTIATING ACYLATION.

Article abstract of DOI:10.1246/bcsj.57.1570

The enantiomer-differentiation acylation (kinetic resolution) of 1-phenylalkylamines and their derivatives was carried out with (S)-2-phenylbutyric anhydride and its derivatives in aqueous and nonaqueous media. On the basis of the distributions of the two diastereomeric products, the molecular interactions between hydrocarbon residues responsible for the structural recognition of the reacting molecules were studied. In nonpolar media, the (R,S)-isomer was predominantly formed over the (S,S)-isomer. Moreover, the differentiation was mainly controlled by the size of the alkyl substituents of the substrates.