NCBI PubMed ID:16263101 Journal NLM ID:0043535 Publisher: Elsevier Correspondence: paul.kosmaboku.ac.at Institutions: Department of Chemistry, University of Natural Resources and Applied Life Sciences, Muthgasse 18, A-1190 Vienna, Austria
d-glycero-d-manno-Heptopyranose 7-phosphate-an intermediate in the biosynthesis of nucleotide-activated heptoses-has been prepared in good overall yield from benzyl 5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-(Z)-hept-5-enofuranoside by a short-step synthesis. Phosphitylation using the phosphoramidite procedure followed by in situ oxidation afforded the corresponding 7-O-phosphotriester derivative in high yield. Subsequent osmylation proceeded in good diastereoselectivity (4:1) to furnish the d-glycero-d-manno-configured derivative, which was separated from the l-glycero-l-gulo-isomer by chromatography. Hydrogenolysis led to simultaneous removal of the benzyl and isopropylidene groups and afforded the target compound in high yield, which serves as a substrate of bacterial heptose 7-phosphate kinases
Methods: chemical synthesis Biosynthesis and genetic data: biosynthetic data Synthetic data: chemical Comments, role: substrate for the bacterial glycosyltransferase involved in the biosynthesis of the S-layer glycoprotein glycan, component of capsular polysaccharide
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