Stereochemistry of terpene derivatives. Part 6: Chemoenzymatic synthesis of chiral bicyclo[3.1.0]hexane derivatives with olfactory properties

Kuriata, Renata; Gajcy, Kamila; Turowska‐Tyrk, Ilona; Lochyński, Stanisław

doi:10.1016/j.tetasy.2010.04.052

Cited by 6 publications

(3 citation statements)

References 15 publications

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“…The enantiopure stereoisomers of the odorous secondary allylic alcohol 222 (Figure ), showing a bicyclo[3.1.0]hexane moiety, and the corresponding esters were prepared, starting from (+)-3-carene, a natural, inexpensive, raw material which is widely available a major component of Polish turpentine obtained from Pinus sylvestris (L).…”

Section: Chiral Fragrances and Flavors By Biocatalyzed Kinetic Resolu...mentioning

confidence: 99%

Biocatalytic Methods for the Synthesis of Enantioenriched Odor Active Compounds

et al. 2011

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Section: Chiral Fragrances and Flavors By Biocatalyzed Kinetic Resolu...mentioning

confidence: 99%

Biocatalytic Methods for the Synthesis of Enantioenriched Odor Active Compounds

et al. 2011

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“…In our previous papers, we described microbiological methods of obtaining new terpenoid derivatives with biological activity such as odorants (Kuriata et al 2010; Kuriata-Adamusiak et al 2011) and insect-feeding deterrents (Wincza and Lochyński 2012). …”

Section: Introductionmentioning

confidence: 99%

“…Despite several disadvantages, microbial transformations are commonly used in organic synthesis towards preparation of homochiral compounds used in agriculture, pharmaceutical, cosmetic, and food industry. In our previous papers, we described microbiological methods of obtaining new terpenoid derivatives with biological activity such as odorants (Kuriata et al 2010 ; Kuriata-Adamusiak et al 2011 ) and insect-feeding deterrents (Wincza and Lochyński 2012 ).…”

Section: Introductionmentioning

confidence: 99%

Application of microorganisms towards synthesis of chiral terpenoid derivatives

Kuriata-Adamusiak

Strub

Lochyński

2012

Appl Microbiol Biotechnol

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Biotransformations are a standard tool of green chemistry and thus are following the rules of sustainable development. In this article, we describe the most common types of reactions conducted by microorganisms applied towards synthesis of chiral terpenoid derivatives. Potential applications of obtained products in various areas of industry and agriculture are shown. We also describe biological activity of presented compounds. Stereoselective hydroxylation, epoxidation, Baeyer–Villiger oxidation, stereo- and enantioselective reduction of ketones, and various kinetic resolutions carried out by bacteria and fungi have been reviewed. Mechanistic considerations regarding chemical and enzymatic reactions are presented. We also briefly describe modern approaches towards enhancing desired enzymatic activity in order to apply modified biocatalysts as an efficient tool and green alternative to chemical catalysts used in industry.

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