127812-04-8Relevant articles and documents
On the mechanism of baker's yeast mediated synthesis of (R) S-benzyl thioglycerate. Experiments in deuterated water
Fronza,Fuganti,Mele,Pedrocchi-Fantoni,Servi
, p. 857 - 864 (1994)
Experiments in ca. 90% deuterated water in which (R) S-benzyl thioglycerate (1) is obtained in the presence of benzyl mercaptan in baker's yeast fermenting on D-mannose, D-glucose and D-fructose, respectively, gave rise to trideuterated materials. The ext
Minor synthetic capacities of baker's yeast towards unnatural substrates
Fronza, Giovanni,Fuganti, Caludio,Grasselli, Piero,Pedrocchi-Fantoni, Giuseppe,Servi, Stefano
, p. 163 - 166 (2007/10/02)
Baker's yeast catalyzes numerous transformations on reactive substrates. α,β-Unsaturated aldehydes undergo water addition with the formation of chiral secondary alcohols, but sulfur nucleophiles (mercaptans) chemically add to the double bond with the partial kinetic resolution observed in the secondary thiol obtained, following enantioselective reduction of the intermediate aldehydes.These sulfur nucleophiles however interact with the yeast metabolic pathway allowing the isolation of carbohydrate derived chiral intermediates.The use of deuterated precursors orperforming the fermentation in D2O allows the isolation of chiral glycerol derivatives stereoselectively deuterated at different positions.
(R)-S-Benzyl Thioglycerate, a New C3 Bifunctional Chiral Material Obtained in Fermenting Baker's Yeast from Benzyl Mercaptan
Fronza, Giovanni,Fuganti, Claudio,Pedrocchi-Fantoni, Giuseppe,Servi, Stefano
, p. 2141 - 2144 (2007/10/02)
Baker's yeast fermenting on D-glucose, produces from benzyl mercaptan (R)-S-benzyl-thioglycerate, converted into (S)-2,2-dimethyl-1,3-dioxolana-4-methanol of 98.6-99percent ee.
