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

• Published in: Journal of organic chemistry Vol. 84; no. 5; pp. 2901 - 2910
• Main Authors: Abayakoon, Palika, Epa, Ruwan, Petricevic, Marija, Bengt, Christopher, Mui, Janice W.-Y, van der Peet, Phillip L, Zhang, Yunyang, Lingford, James P, White, Jonathan M, Goddard-Borger, Ethan D, Williams, Spencer J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.03.2019; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; OXIDATION; ACID; ASYMMETRIC DIHYDROXYLATION; SULFOQUINOVOSE; DEGRADATION; ALPHA; SUGAR
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/acs.joc.9b00055

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.