Comprehensive Synthesis of Substrates, Intermediates, and Products of the Sulfoglycolytic Embden–Meyerhoff–Parnas Pathway

Sulfoglycolysis
is a metabolic pathway dedicated to the catabolism of the sulfosugar
sulfoquinovose (SQ) into smaller organosulfur fragments. An estimated
10 billion tonnes of SQ fluxes through sulfoglycolysis pathways each
year, making it a significant aspect of the biogeochemical sulfur
cycle. Delineating the molecular details of sulfoglycolysis requires
authentic samples of the various metabolites in these pathways. To
this end, we have established chemical and chemoenzymatic methods
for the synthesis of the key organosulfur metabolites sulfoquinovosylglycerol,
SQ (also in 13C6-labeled form), sulfofructose,
sulfofructose-1-phosphate, sulfolactaldehyde, and 2,3-dihydroxypropanesulfonate,
as well as an improved route to the chromogenic sulfoquinovosidase
substrate 4-nitrophenyl α-sulfoquinovoside.