Switching from (R)- to (S)-selective chemoenzymatic DKR of amines involving sulfanyl radical-mediated racemization.
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.
El Blidi
Lahssen
L
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.
Vanthuyne
Nicolas
N
Siri
Didier
D
Gastaldi
Stéphane
S
Bertrand
Michèle P
MP
Gil
Gérard
G
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*
D000577:Amides; D000588:Amines; D001426:Bacterial Proteins; D005609:Free Radicals; D009570:Nitriles; D013438:Sulfhydryl Compounds; D010450:Endopeptidases; C087822:alkaline protease; C004526:azobis(isobutyronitrile)