Formate → HCID 11083910, compound

Participants

Reaction Conditions

Reaction Steps

MVS/GG (6 units (μ moles/minute/30° C.)) and yeast formate dehydrogenase (5 units) were added to a solution of 4-methyl-2-oxo-3-pentenoic acid (1.0 mM) in deoxygenated Tris buffer (5 mM:pH 6.0; 80 ml) containing NADH (0.02 mM), sodium formate (3.1 mM), fructose-1,6-bisphosphate (0.4 mM) and dithiothreitol (0.08 mM). The solution was stirred at room temperature (-20° C.) under nitrogen for 5 days with periodic addition of 0.2 mM HCl to maintain pH in the range of 6.0-6.2. Acidification to pH 2.0 and extractive work-up with ethyl acetate gave (S)-2-hydroxy-4-methyl-3-pentenoic acid in 91% isolated yield. Analysis of the (R)-MTPA derivative and comparison to a racemic standard gave a value of at least 99% for entantiomeric excess.

Provenance & Evidence