Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. 17455-13-9, Name is 1,4,7,10,13,16-Hexaoxacyclooctadecane, molecular formula is C12H24O6, belongs to chiral-catalyst compound. In a document, author is Wu, Yanfei, introduce the new discover, Quality Control of 1,4,7,10,13,16-Hexaoxacyclooctadecane.
(S)-N-Boc-3-hydroxypiperidine [(S)-NBHP] is a key intermediate for the synthesis of mantle cell lymphoma drug, ibrutinib. Here, KpADH, an alcohol dehydrogenase from Kluyveromyces polyspora, exhibits evolutionary potential in the asymmetric reduction of N-Boc-3-piperidone (NBPO) to (S)-NBHP. By screening key residues in substrate binding pocket of KpADH, an excellent variant Y127W was obtained with 6-fold improved activity of 119.3 U mg(-1), 1.8-fold enhanced half-life of 147 h and strict S-stereoselectivity (>99% ee). When catalyzed by Y127W, a complete conversion of 600 g L-1 NBPO was achieved at a substrate to catalyst ratio (S/C) of 30 in 10 h. Based on crystal-structure of Y127W, molecular docking and dynamic simulations reveal hydrogen bonds formed between W127 and Boc group of NBPO, as well as improved structural stability mainly contribute to the increased catalytic activity and stereoselectivity of Y127W. This study offers guidance for engineering ADHs for biosynthesis of chiral heterocyclic alcohols, and provides insights into mechanisms in catalytic activity and stereoselectivity toward carbonyl-containing heterocyclic substrates.
Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law. In my other articles, you can also check out more blogs about 17455-13-9. Quality Control of 1,4,7,10,13,16-Hexaoxacyclooctadecane.
Reference:
Chiral Catalysts,
,Chiral catalysts – SlideShare