title: Switching from (R)- to (S)-selective chemoenzymatic DKR of amines involving sulfanyl radical-mediated racemization.
abstract: Chemoenzymatic dynamic kinetic resolution (DKR) of amines involving sulfanyl radical-induced racemization happened to be the very first switchable DKR process allowing the synthesis of either (R)- or (S)-amides, in good yield and high enantiomeric excess, depending on the nature of the enzyme; the different steps of the development of (S)-selective DKR are discussed.
authors.affiliation: Equipe Chimie Moléculaire Organique, LCP UMR 6264, Boite 562, Université Paul Cézanne, Faculté des Sciences St Jérôme, Avenue Escadrille Normandie-Niemen, 13397, Marseille Cedex 20, France.
authors.forename: Lahssen
authors.initials: L
authors.lastname: El Blidi
authors.forename: Nicolas
authors.initials: N
authors.lastname: Vanthuyne
authors.forename: Didier
authors.initials: D
authors.lastname: Siri
authors.forename: Stéphane
authors.initials: S
authors.lastname: Gastaldi
authors.forename: Michèle P
authors.initials: MP
authors.lastname: Bertrand
authors.forename: Gérard
authors.initials: G
authors.lastname: Gil
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D001426:Bacterial Proteins / Q000737:chemistry / Q000378:metabolism*; D055162:Biocatalysis; D010450:Endopeptidases / Q000737:chemistry / Q000378:metabolism*; D005609:Free Radicals / Q000737:chemistry; D007700:Kinetics; D009570:Nitriles / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000577:Amides; D000588:Amines; D001426:Bacterial Proteins; D005609:Free Radicals; D009570:Nitriles; D013438:Sulfhydryl Compounds; D010450:Endopeptidases; C087822:alkaline protease; C004526:azobis(isobutyronitrile)