5-hydroxypentane-2,3-dione (Laurencione), a bacterial metabolite of 1- deoxy-D-threo-pentulose

Article abstract of DOI:10.1016/S0040-4039(98)01301-X

Cell-free systems from the bacteria Escherichia coli and Klebsiella planticola that were incubated with ¹³C labeled pyruvate and D- glyceraldehyde synthesized 5-hydroxypentane-2,3-dione (laurencione) along with 1-deoxy-D-threo-pentulose (1-deoxy-D-xylulose). Both compounds showed identical labeling patterns, indicating that the C₅ skeletons were derived from the condensation of (hydroxyethyl)thiamin on D-glyceraldehyde. Conversion of [5,5-²H₂]deoxyxylulose into laurencione by a cell-free system from E. coli showed that the α-dione is obtained from the pentulose by water elimination.