14035-95-1Relevant articles and documents
Terent'ev,Freidlina
, (1973)
Steric effects on the stereochemistry of old yellow enzyme-mediated reductions of unsaturated diesters: Flipping of the substrate within the enzyme active site induced by structural modifications
Brenna, Elisabetta,Gatti, Francesco G.,Manfredi, Alessia,Monti, Daniela,Parmeggiani, Fabio
, p. 2859 - 2864 (2013/01/15)
The ene-reductase-mediated reduction of the carbon-carbon double bond of some alkyl 2- substituted butenedioates was investigated. The stereochemical outcome of the reaction was found to be influenced by steric effects. Ethyl and butyl citraconates were converted into the corresponding alkyl (R)-2-methylsuccinates with excellent enantioselectivity, whereas ethyl and butyl mesaconates were completely unreactive. Methyl 2-substituted fumarates were reduced to enantiomerically enriched methyl (S)-2-substituted succinates, whereas the (Z)-stereoisomers were left unreacted by enereductases. Labelling experiments were performed to investigate the mechanism of these bioreductions and explain their stereochemical outcome.