20548-03-2Relevant articles and documents
Enantio- A nd regioselective: Ene-reductions using F420H2-dependent enzymes
Mathew, Sam,Trajkovic, Milos,Kumar, Hemant,Nguyen, Quoc-Thai,Fraaije, Marco W.
supporting information, p. 11208 - 11211 (2018/10/15)
In the past decade it has become clear that many microbes harbor enzymes that employ an unusual flavin cofactor, the F420 deazaflavin cofactor. Herein we show that F420-dependent reductases (FDRs) can successfully perform enantio-, regio- A nd chemoselective ene-reductions. For the first time, we have demonstrated that F420H2-driven reductases can be used as biocatalysts for the reduction of α,β-unsaturated ketones and aldehydes with good conversions (>99%) and excellent regioselectivities and enantiomeric excesses (>99% ee). Noteworthily, FDRs typically display an opposite enantioselectivity when compared to the well established FMN-dependent Old Yellow Enzymes (OYEs).
Structure-odor correlation, XXIV: Synthesis and olfactory properties of damascene and damascenone analogs
Weyerstahl, Peter,Licha, Kai
, p. 809 - 814 (2007/10/03)
The aldehydes rac-1, rac-2, and 3 were conveniently prepared by starting from isophorone (4). Reaction of 1-3 with (E,Z)-1-bromo-1-propene (14) afforded the rac-allylic alcohols (E,Z)-15, -18, and -20. The alcohols were oxidized to the damascone/damascenone analogs 1-(3,5,5-trimethyl-2-cyclohexen-1-yl)- (rac-16), 1-(3,5,5-trimethyl-1-cyclohexen-1-yl)-(rac-19), and 1-(3,5,5-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one (21), and the (E/Z) isomers were separated by FC. Their olfactory evaluation shows that the highly estimated odor of damascone (A, B) and damascenone (C) is more or less lost. This result can be explained by force-field calculation of the lowest energy conformation of 16, 19, and 21 in comparison with those of A-C. VCH Verlagsgesellschaft mbH, 1996.
Microbial Conversion of 4-Oxoisophorone by Aspergillus niger
Yamazaki, Yoshinari,Hayashi, Yumiko,Hori, Nobuaki,Mikami, Yoichi
, p. 2919 - 2920 (2007/10/02)
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