Bioreduction of α-methylcinnamaldehyde derivatives: chemo-enzymatic asymmetric synthesis of Lilial™ and Helional™
2010; Royal Society of Chemistry; Volume: 39; Issue: 36 Linguagem: Inglês
10.1039/c002971h
ISSN1477-9234
AutoresClemens Stueckler, Nicole J. Mueller, Christoph K. Winkler, Silvia M. Glueck, Karl Gruber, Georg Steinkellner, Kurt Faber,
Tópico(s)Plant biochemistry and biosynthesis
ResumoNonracemic aryl-substituted α-methyldihydrocinnamaldehyde derivatives employed as olfactory principles in perfumes (Lilial™, Helional™) were obtained via enzymatic reduction of the corresponding cinnamaldehyde precursors using cloned and overexpressed ene-reductases. (R)-Enantiomers were obtained using the old-yellow-enzyme (OYE) homolog YqjM from Bacillus subtilis and 12-oxophytodienoic acid reductase isoenzyme OPR1 from tomato (e.e.max 53%), and (S)-aldehydes were furnished in up to 97% e.e. using isoenzyme OPR3, nicotinamide 2-cyclohexene-1-one reductase NCR from Zymomonas mobilis and yeast OYE isoenzymes 1–3 under optimised reaction conditions in the presence of t-butyl methyl ether as the co-solvent. The stereochemical outcome of the reduction of α-methylcinnamaldehyde using NCR and OYEs 1–3 [previously reported to be (R)] was unambiguously corrected to be (S).
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