期刊
CHEMBIOCHEM
卷 22, 期 17, 页码 2693-2696出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.202100290
关键词
asymmetric catalysis; asymmetric hydrogenation; flavin adenine dinucleotide; lipids; oxidoreductases
资金
- Projekt DEAL
The study tested two FAD-dependent archaeal geranylgeranyl reductases for the asymmetric reduction of unfunctionalized C=C bonds, achieving promising results and opening new opportunities for the synthesis of enantiopure branched alkyl chains.
The asymmetric reduction of activated C=C bonds such as enones is well established for non-enzymatic methods as well as in biocatalysis. However, the asymmetric reduction of unfunctionalized C=C bonds is mainly performed with transition metal catalysts whereas biocatalytic approaches are lacking. We have tested two FAD-dependent archaeal geranylgeranyl reductases (GGR) for the asymmetric reduction of isolated C=C bonds. The reduction of up to four double bonds in terpene chains with different chain lengths and head groups was confirmed. Methyl-branched E-alkenes were chemoselectively reduced in the presence of cyclic, terminal or activated alkenes. Using a removable succinate spacer, farnesol and geraniol could be quantitatively reduced (>99 %). The reduction is strictly (R)-selective (enantiomeric excess >99 %). Hence, GGRs are promising biocatalysts for the asymmetric reduction of unactivated isolated C=C bonds, opening new opportunities for the synthesis of enantiopure branched alkyl chains.
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