Intrinsic and environmental modulation of stereoselective aldol organocatalyzed reactions by proline-containing lipopeptides.

ABSTRACT: Proline, along with its derivatives, has been employed as an efficient organocatalyst for aldol reactions, with the ability to promote the creation of stereoselective C-C bonds. Even though the Houk-List transition state model is able to explain the stereoselectivity observed when proline is used as a catalyst, few studies investigate the role of microheterogeneous media in modulating the reaction outcome. In this work, molecular dynamics and electronic structure calculations were used to investigate the aldol reaction in the condensed phase. Our research focused on a lipopeptide compound incorporating the proline residue within the sequence PRWG-(C₁₈H₃₇), where P represents l-proline, R stands for l-arginine, W for l-tryptophan, and G for l-glycine. This sequence is

SUBMITTER: Sodre PT 

PROVIDER: S-EPMC11220607 | biostudies-literature | 2024 Jun

REPOSITORIES: biostudies-literature