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RESEARCH PRODUCT
Influence of structural factors and enzyme type on the reactivity and enantioselectivity of the enzymatic esterification of bicyclic meso dialcohols
J. Alberto MarcoCecilia AndreuGregorio Asensiosubject
Inorganic Chemistrychemistry.chemical_compoundCyclopentadienechemistryBicyclic moleculeMeso compoundFuranMaleic anhydrideSubstrate (chemistry)Organic chemistryReactivity (chemistry)Solvent effectsdescription
The meso dialcohols 1–7, obtained from the Diels-Alder adducts furan/maleic anhydride, furan/dimethyl acetylenedi-carboxylate, and cyclopentadiene/maleic anhydride, were subjected to enzymatic esterification in organic solvents. A mixture of the corresponding chiral monoacetates and the meso diacetates was obtained. It has been found that reaction rate and enantioselectivity markedly depend on substrate structure, temperature, enzyme type, and nature of the solvent. The presence of an oxygen bridge and an exo configuration are the two structural features which lead to the highest enantioselectivity values.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1992-10-01 | Chemische Berichte |