A short synthesis of D-glycero-D-manno-heptose 7-phosphate.
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-alpha-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.
Güzlek
Hacer
H
Department of Chemistry, University of Natural Resources and Applied Life Sciences, Muthgasse 18, A-1190 Vienna, Austria.
Graziani
Andrea
A
Kosma
Paul
P
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis / Q000737:chemistry; D006539:Heptoses / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010429:Pentoses / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013403:Sugar Phosphates / Q000138:chemical synthesis* / Q000737:chemistry
D019086:Bridged Bicyclo Compounds, Heterocyclic; D006539:Heptoses; D010429:Pentoses; D013403:Sugar Phosphates; C508703:benzyl 5,6-dideoxy-2,3-O-isopropylidene-lyxo-hept-5-enofuranoside; C508702:glycero-manno-heptopyranose 7-phosphate