Phosphoenolpyruvate as a dual purpose reagent for integrated nucleotide/nicotinamide cofactor recycling.
An efficient technique is presented which integrates cofactor dependent enzymic phosphorylation and dehydrogenation into a single, closed-loop system by employing phosphoenolpyruvate as the sacrificial reagent for sequential ATP and NAD+ recycling steps. Exemplary applications are developed for the synthesis of 6-phosphogluconate from glucose, and that of dihydroxyacetone phosphate from glycerol. The latter system is combined with exergonic diastereoselective aldol additions for the one-flask synthesis of a ketosugar (D-sorbose), thiosugar (L-threo-5-thiopentulose), or a sugar acid (L-threo-pent-4-ulosonic acid) starting from a mixture of glycerol and simple aldehydes.
Fessner
W D
WD
Department of Organic Chemistry and Biochemistry, University of Freiburg, Germany.
Sinerius
G
G
D000255:Adenosine Triphosphate / Q000378:metabolism*; D000818:Animals; D005942:Gluconates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D005947:Glucose / Q000378:metabolism; D005954:Glucosephosphate Dehydrogenase; D006593:Hexokinase; D007202:Indicators and Reagents; D007770:L-Lactate Dehydrogenase; D009682:Magnetic Resonance Spectroscopy; D009132:Muscles / Q000201:enzymology; D009243:NAD / Q000378:metabolism*; D010728:Phosphoenolpyruvate / Q000378:metabolism; D011770:Pyruvate Kinase; D011817:Rabbits; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D013403:Sugar Phosphates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
D005942:Gluconates; D007202:Indicators and Reagents; D013403:Sugar Phosphates; D009243:NAD; D010728:Phosphoenolpyruvate; D000255:Adenosine Triphosphate; D007770:L-Lactate Dehydrogenase; D005954:Glucosephosphate Dehydrogenase; D006593:Hexokinase; D011770:Pyruvate Kinase; D005947:Glucose; C008884:6-phosphogluconic acid