Yeast-mediated preparation of l-PAC in an organic solvent.
The yeast-mediated acyloin condensation of benzaldehyde and pyruvic acid to form l-PAC occurs in a petroleum spirit solvent system at room temperature with moderate conversion (30%) and high enantioselectivity (86%ee) after 24 h. The addition of a small amount of ethanol (0.5% mL) to the reaction mixture inhibits the formation of the side product benzyl alcohol and increases the conversion to l-PAC. Conducting the reaction using 13C labeled pyruvate indicated that the pyruvate was incorporated into the l-PAC and that the excess pyruvate was converted into ethanol. Conducting the reaction at 5 degrees C results in similar conversion but higher enantioselectivity.
Kostraby
Margaret M
MM
Smallridge
Andrew J
AJ
Trewhella
Maurie A
MA
D000096:Acetone / Q000031:analogs & derivatives* / Q000037:antagonists & inhibitors / Q000138:chemical synthesis*; D001547:Benzaldehydes / Q000737:chemistry; D002021:Buffers; D002849:Chromatography, Gas; D000431:Ethanol / Q000378:metabolism; D005285:Fermentation; D008279:Magnetic Resonance Imaging; D019289:Pyruvic Acid / Q000378:metabolism; D012441:Saccharomyces cerevisiae / Q000201:enzymology*
D001547:Benzaldehydes; D002021:Buffers; D000096:Acetone; D000431:Ethanol; D019289:Pyruvic Acid; C035293:1-hydroxy-1-phenyl-2-propanone