Premium
Enzymatic Asymmetric Reduction of Unfunctionalized C=C Bonds with Archaeal Geranylgeranyl Reductases
Author(s) -
Cervinka Richard,
Becker Daniel,
Lüdeke Steffen,
Albers SonjaVerena,
Netscher Thomas,
Müller Michael
Publication year - 2021
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.202100290
Subject(s) - enantiopure drug , biocatalysis , chemistry , double bond , stereochemistry , enantioselective synthesis , enantiomeric excess , alkyl , catalysis , organic chemistry , combinatorial chemistry , reaction mechanism
Abstract 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.