Microbiological transformations. Part 39: Determination of the regioselectivity occurring during oxirane ring opening by epoxide hydrolases: A theoretical analysis and a new method for its determination

Tetrahedron Asymmetry

Volumn 9, Issue 9, 1998, Pages 1539-1547

  Moussou, Philippe ^a   Archelas, Alain ^a   Baratti, Jacques ^a   Furstoss, Roland ^a  

^a ETABLISSEMENT FRANÇAIS DU SANG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; EPOXIDE HYDROLASE;

ARTICLE; CONFORMATIONAL TRANSITION; ENANTIOMER; ENZYME ACTIVITY; HYDROLYSIS; MATHEMATICAL ANALYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032496192     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00122-0     Document Type: Article

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29. 1 is the one bearing the 'bulkier' substituent.
30. Due to this convention, the ees will be positive if the (1S)-epoxide is the slow reacting enantiomer, whereas it will be negative if it is the (1R)-epoxide. Similarly, the eep will be positive if the (1R)-diol is formed preferentially, whereas it will be negative if it is the (1S)-diol.
31. The regioselectivity coefficients were calculated by non-linear regression of Eq. 7 using the commercial Jandel software Sigmaplot® (Marquardt-Levenberg algorithm).
32. By convention, the epoxide enantiomer which is framed is the faster hydrolyzed one and the diol enantiomer framed is the one formed in excess.