Mechanistic Insight into the Origin of Stereoselectivity in the Ribose-Mediated Strecker Synthesis of Alanine
Luca Legnani, Andrea Darù, Alexander X. Jones, Donna G. Blackmond
Abstract
Enantioenriched amino acids are produced in a hydrolytic kinetic resolution of racemic aminonitriles mediated by chiral pentose sugars. Experimental kinetic and spectroscopic results combined with DFT computational studies and microkinetic modeling help to identify the nature of the intermediate species and provide insight into the stereoselectivity of their hydrolysis in the prebiotically relevant ribose-alanine system. These studies support a synergistic role for sugars and amino acids in the emergence of homochirality in biological molecules.
Topics & Concepts
ChemistryStrecker amino acid synthesisKinetic resolutionStereoselectivityHomochiralityHydrolysisRibosePentoseAlanineAmino acidStereochemistryOrganic chemistryEnantiomerEnantioselective synthesisBiochemistryEnzymeCatalysisFermentationOrigins and Evolution of LifePhotoreceptor and optogenetics researchProtein Structure and Dynamics