Abstract:The kinetics of enzymatic desymmetrisation were analysed for the most common kinetic mechanisms: ternary complex ordered (prochiral ketone reduction); ping-pong second (ketone amination, diol esterification, desymmetrisation in the second half reaction); ping-pong first (diol ester hydrolysis) and ping-pong both (prochiral diacids). For plausible values of enzyme kinetic parameters, the product enantiomeric excess (ee) can decline substantially as the reaction proceeds to high conversion. For example, an ee of… Show more
“…Following enantioselective oxidation of 56 to form monoaldehyde ( maj )- 57 , further GOase oxidation is also highly stereoselective, resulting in preferential conversion of the minor atropisomer ( min )- 57 to dialdehyde 58 . This results in further enantioenrichment of 57 over time, albeit at the expense of yield …”
“…Following enantioselective oxidation of 56 to form monoaldehyde ( maj )- 57 , further GOase oxidation is also highly stereoselective, resulting in preferential conversion of the minor atropisomer ( min )- 57 to dialdehyde 58 . This results in further enantioenrichment of 57 over time, albeit at the expense of yield …”
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