Biocatalytic preparation of enantioenriched 3,4-dihydroxypiperidines and theoretical study of Candida antarctica lipase B enantioselectivity

Glycosynthase‐Mediated Assembly of Xylanase Substrates and Inhibitors

“…Benzyl (3 R ,4 R )‐3,4‐diacetoxy‐piperidine‐1‐carboxylate: 1 H and 13 C NMR spectra obtained for this compound were in agreement with the data previously reported 40…”

An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one

“…These results reveal a new type of stereoselective behavior of CAL B, which has been rationalized by molecular modeling. 31 We have also examined these enzymatic reactions using molecular modeling, in order to understand the structural relation between the enzymatic pocket and the characteristic steroidal framework, which accounts for the remarkable selectivity of the biological behavior of these compounds. In fact, only the 20b isomers have biological activity and would be useful in the preparation of steroideprotein conjugates.…”

Molecular modeling of the lipase-catalyzed hydrolysis of acetoxymethyl(i-propoxy)phenylphosphine oxide and its P-borane analogue

“…We have used the protocol that has been successfully applied to rationalize the selectivity of the enzyme-aided hydrolysis of esters [26][27][28][29][30][31][32][33][34][35][36]. The enantioselectivity of the hydrolysis stems from the difference in the potential energy between the substrates and the corresponding transition state.…”