Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 65, Issue 21, Pages 6940-6943Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo000492y
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A total of four enzymatic steps were combined, in a: one-pot reaction, to synthesize carbohydrates starting from glycerol. First, phosphorylation of glycerol by reaction with pyrophosphate in the presence of phytase at pH 4.0 in 95% glycerol afforded racemic glycerol-3-phosphate in 100% yield. The L-enantiomer of the latter underwent selective aerobic oxidation to dihydroxyacetone phosphate (DHAP) at pH 7.5 in the presence of glycerolphosphate oxidase (GPO) and catalase. Subsequently, fructose-1,6-bisphosphate aldolase catalyzed the aldol reaction of DHAP with butanal. Finally, dephosphorylation of the aldol adduct was mediated by phytase at pH 4 affording 5-deoxy-5-ethyl-D-xylulose in, 57% yield from L-glycerol-3-phosphate. The phytase on/off-snitch by pH was the key to controlling phosphorylation and dephosphorylation.
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