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- W1976299542 abstract "Carboxylesterases containing the sequence motif GGGX catalyze the hydrolysis of esters of chiral tertiary alcohols, albeit with only low to moderate enantioselectivity, for three model substrates (linalyl acetate, methyl-1-pentin-1-yl acetate, 2-phenyl-3-butin-2-yl acetate). In order to understand the molecular mechanism of enantiorecognition and to improve enantioselectivity for this interesting substrate class, the interaction of both enantiomers with the substrate binding sites of acetylcholinesterases and p-nitrobenzyl esterase from Bacillus subtilis was modeled and correlated to experimental enantioselectivity. For all substrate-enzyme pairs, enantiopreference and ranking by enantioselectivity could be predicted by the model. In p-nitrobenzyl esterase, one of the key residues in determining enantioselectivity was G105: exchange of this amino acid for an alanine residue led to a sixfold increase of enantioselectivity (E = 19) towards 2-phenyl-3-butin-2-yl acetate. However, the effect of this mutation is specific: the same mutant had the opposite enantiopreference towards the substrate linalyl acetate. Thus, depending on the substrate structure, the same mutant has either increased enantioselectivity or opposite enantiopreference compared to the wild-type enzyme." @default.
- W1976299542 created "2016-06-24" @default.
- W1976299542 creator A5031181844 @default.
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- W1976299542 date "2003-06-02" @default.
- W1976299542 modified "2023-10-16" @default.
- W1976299542 title "A Molecular Mechanism of Enantiorecognition of Tertiary Alcohols by Carboxylesterases" @default.
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- W1976299542 doi "https://doi.org/10.1002/cbic.200200518" @default.
- W1976299542 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/12794858" @default.
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