Stefano Serra , Davide De Simeis , Elisabetta Brenna
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引用次数: 8
Abstract
The four isomeric forms of the flavour linalool oxide (pyranoid) were synthesized starting from the inexpensive monoterpene terpinolene. The key steps of the process include mCPBA epoxidation of the starting diene, alumina-catalysed rearrangement of the obtained diepoxide and the diastereoselective reduction of the ketone 2,2,6-trimethyl-6-vinyldihydro-2H-pyran-3(4H)-one. The resulting racemic cis- and trans-linalool oxides were resolved through an enzyme-mediated acetylation procedure. More specifically, we found that Candida rugosa lipase and lipase PS are the catalysts of choice for the resolution of cis- and trans-linalool oxide, respectively.
期刊介绍：
Journal of Molecular Catalysis B: Enzymatic is an international forum for researchers and product developers in the applications of whole-cell and cell-free enzymes as catalysts in organic synthesis. Emphasis is on mechanistic and synthetic aspects of the biocatalytic transformation.
Papers should report novel and significant advances in one or more of the following topics;
Applied and fundamental studies of enzymes used for biocatalysis;
Industrial applications of enzymatic processes, e.g. in fine chemical synthesis;
Chemo-, regio- and enantioselective transformations;
Screening for biocatalysts;
Integration of biocatalytic and chemical steps in organic syntheses;
Novel biocatalysts, e.g. enzymes from extremophiles and catalytic antibodies;
Enzyme immobilization and stabilization, particularly in non-conventional media;
Bioprocess engineering aspects, e.g. membrane bioreactors;
Improvement of catalytic performance of enzymes, e.g. by protein engineering or chemical modification;
Structural studies, including computer simulation, relating to substrate specificity and reaction selectivity;
Biomimetic studies related to enzymatic transformations.
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