Archelas, Alain et al. published new progress in experiments with the help of cas: 579-43-1

Desymmetrization of rel-(1R,2S)-1,2-Diphenylethane-1,2-diol(cas:579-43-1 Name: rel-(1R,2S)-1,2-Diphenylethane-1,2-diol) using chiral phosphine catalyst has been reported. Conversion of meso-hydrobenzoin to trans-stillbene oxide by treatment with an aryl sulfonyl chloride and aqueous sodium hydroxide has been reported.

Name: rel-(1R,2S)-1,2-Diphenylethane-1,2-diolIn 2016, Archelas, Alain;Zhao, Wei;Faure, Bruno;Iacazio, Gilles;Kotik, Michael published 《Epoxide hydrolase-catalyzed enantioselective conversion of trans-stilbene oxide: Insights into the reaction mechanism from steady-state and pre-steady-state enzyme kinetics》. 《Archives of Biochemistry and Biophysics》published the findings. The article contains the following contents:

A detailed kinetic study based on steady-state and pre-steady-state measurements is described for the highly enantioselective epoxide hydrolase Kau2. The enzyme, which is a member of the α/β-hydrolase fold family, preferentially reacts with the (S,S)-enantiomer of trans-stilbene oxide (TSO) with an E value of ∼200. The enzyme follows a classical two-step catalytic mechanism with formation of an alkyl-enzyme intermediate in the first step and hydrolysis of this intermediate in a rate-limiting second step. Tryptophan fluorescence quenching during TSO conversion appears to correlate with alkylation of the enzyme. The steady-state data are consistent with (S,S) and (R,R)-TSO being two competing substrates with marked differences in kcat and Km values. The high enantiopreference of the epoxide hydrolase is best explained by pronounced differences in the second-order alkylation rate constant (k2/KS) and the alkyl-enzyme hydrolysis rate k3 between the (S,S) and (R,R)-enantiomers of TSO. Our data suggest that during conversion of (S,S)-TSO the two active site tyrosines, Tyr157 and Tyr259, serve mainly as electrophilic catalysts in the alkylation half-reaction, polarizing the oxirane oxygen of the bound epoxide through hydrogen bond formation, however, without fully donating their hydrogens to the forming alkyl-enzyme intermediate.rel-(1R,2S)-1,2-Diphenylethane-1,2-diol (cas: 579-43-1) were involved in the experimental procedure.

Desymmetrization of rel-(1R,2S)-1,2-Diphenylethane-1,2-diol(cas:579-43-1 Name: rel-(1R,2S)-1,2-Diphenylethane-1,2-diol) using chiral phosphine catalyst has been reported. Conversion of meso-hydrobenzoin to trans-stillbene oxide by treatment with an aryl sulfonyl chloride and aqueous sodium hydroxide has been reported.

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