biostudies-literatureKim BDivision of ChemistryDeutsche ForschungsgemeinschaftNational Institute of General Medical SciencesNIGMS NIH HHS15239-15244https://www.ebi.ac.uk/biostudies/studies/S-EPMC5735348biostudies-literatureUnknown139(42)Since the discovery of molecular chirality, nonsuperimposable mirror-image organic molecules have been found to be essential across biological and chemical processes and increasingly in materials science. Generally, carbon centers containing four different substituents are configurationally stable, unless bonds to the stereogenic carbon atom are broken and re-formed. Herein, we describe sp³-stereogenic carbon-bearing molecules that dynamically isomerize, interconverting between enantiomers without cleavage of a constituent bond, nor through remote functional group migration. The stereodynamic molecules were designed to contain a pair of redox-active substituents, quinone and hydroquinone groups, which allow the enantiomerization to occur via redox-interconversion. In the presencJournal of the American Chemical SocietyStereodynamic Quinone-Hydroquinone Molecules That Enantiomerize at sp³-Carbon via Redox-Interconversion.PMC5735348R01 GM096403R01-GM050422CHE-1609434STO 1175/1-1R01-GM096403R01 GM050422Castillo-Lora JKim BStorch GMercado BQBanerjee GMayer JMMiller SJBrudvig GWfalseStereodynamic Quinone-Hydroquinone Molecules That Enantiomerize at sp³-Carbon via Redox-Interconversion.Since the discovery of molecular chirality, nonsuperimposable mirror-image organic molecules have been found to be essential across biological and chemical processes and increasingly in materials science. Generally, carbon centers containing four different substituents are configurationally stable, unless bonds to the stereogenic carbon atom are broken and re-formed. Herein, we describe sp³-stereogenic carbon-bearing molecules that dynamically isomerize, interconverting between enantiomers without cleavage of a constituent bond, nor through remote functional group migration. The stereodynamic molecules were designed to contain a pair of redox-active substituents, quinone and hydroquinone groups, which allow the enantiomerization to occur via redox-interconversion. In the presenc2017-01-01T00:00:00Z2017 Oct2025-04-22T16:09:27.671Z2019-03-27T00:03:40ZS-EPMC57353482893128010.1021/jacs.7b09176