Stereochemistry of valine biosynthesis. Configuration of the product of rearrangement of alpha-acetolactate.
When alpha-aceto[1,3,5-13C3]lactate (2-hydroxy-2-methyl-3-oxo[1,3,5-13C3]butanoate) was incubated with a cell-free system prepared from Salmonella typhimurium, the valine produced was labelled in the C-4 pro-S position. This result proves that during the tertiary ketol rearrangement catalysed by the reductoisomerase of the isoleucine-valine pathway, the methyl group transfer is to the re face of the trigonal centre at C-3 of alpha-acetolactate.
D002247:Carbon Isotopes; D002474:Cell-Free System; D007553:Isotope Labeling; D007773:Lactates / Q000138:chemical synthesis / Q000378:metabolism*; D008968:Molecular Conformation; D009154:Mutation; D012486:Salmonella typhimurium / Q000378:metabolism*; D013329:Structure-Activity Relationship; D014633:Valine / Q000096:biosynthesis*
D002247:Carbon Isotopes; D007773:Lactates; C006359:alpha-acetolactate; D014633:Valine