Elucidating the Racemization Mechanism of Aliphatic and Aromatic Amino Acids by In Silico Tools.

ABSTRACT: The racemization of biomolecules in the active site can reduce the biological activity of drugs, and the mechanism involved in this process is still not fully comprehended. The present study investigates the impact of aromaticity on racemization using advanced theoretical techniques based on density functional theory. Calculations were performed at the ωb97xd/6-311++g(d,p) level of theory. A compelling explanation for the observed aromatic stabilization via resonance is put forward, involving a carbanion intermediate. The analysis, employing Hammett's parameters, convincingly supports the presence of a negative charge within the transition state of aromatic compounds. Moreover, the combined utilization of natural bond orbital (NBO) analysis and intrinsic reaction coordinate (IRC) calculati

SUBMITTER: Andino MS 

PROVIDER: S-EPMC10418343 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature