Carboxylesterase , stereoselective

Huang H, Fleming CD, Nishi K, Redinbo MR, Hammock BD (2005) Stereoselective hydrolysis of pyrethroid-like fluorescent substrates by human and other mammalian liver carboxylesterases. ChemRes Toxicol 18 1371-1377... 

R. B. Melchert, C. Goldlin, U. Zweifel, A. A. Welder, U. A. Boelsterli, Differential Toxicity of Cocaine and Its Enantiomers, (+)-Cocaine and (-)- -Cocaine, is Associated with Stereoselective Hydrolysis by Hepatic Carboxylesterases in Cultured Rat Hepatocytes , Chem.-Biol. Interact. 1992, 84, 243-258. 

Nishizawa M, Gomi H et al (1993) Purification and some properties of carboxylesterase from Arthrobacter globiformis, stereoselective hydrolysis of ethyl chrysanthemate. Biosci Biotech Biochem 57 594-598... 

Chang et al. (2009) reported the viability of using a consensus 3D QSAR pharmacophore model to predict the stereospecific rat serum carboxylesterase (CEs) hydrolysis rates and half lives for the pyrethroids. Utilizing a stereoselective in vitro metabolism dataset from Sprague-Dawley rat serum CES, and 27 Type I and II pyrethroids, a ligand-derived pharmacophore model was developed to filter catalytically competent and incompetent ligands, that were based on four pharmacophore features (i.e., two aromatic, and two projected hydrogen bond... 

Table 19 Predicted stereoselective hydrolysis rates (kj-at) for rat serum carboxylesterase...

Chang DT, Goldsmith M-R, Tomero-Velez L-J, Ulrich E, Lindstrom AB, Dary CC (2009) A novel application of QSAR and PH4 models for the elucidation of the stereoselective hydrolysis rates of pyrethroids by rat serum carboxylesterase. Society of Environmental Toxicology and Chemistry, New Orleans, LA, November 2009 meeting. 

The enzymatic activity of lipases is very comparable to that of esterases, with the main difference being the chain length and hydrophobicity of the acid moiety of the substrate. Therefore in fine chemical applications, lipases and esterases are being used as alternatives for several conversions. For instance, for the kinetic resolution of 2-arylpropionic acids such as naproxen and ibu-profen, both a lipase and an esterase have been found that can perform a stereoselective hydrolysis yielding the pharmaceutically preferred enantiomer S-naproxen (Bertola et al. 1992 Hedstrom et al. 1993). High activity and ease of production have made the carboxylesterase from Bacillus subtilis Thai 1-8 the prime choice of industry (Quax and Broekhuizen 1994). 

Hemmert, A.C., Otto, T.C., Wierdl, M., et al., 2010. Human carboxylesterase 1 stereoselectively binds the nerve agent cyclosarin and spontaneously hydrolyzes the nerve agent sarin. Mol. Pharmacol. 77,508-516. 

---