A convenient synthesis of GDP D-glycero-alpha-D-manno-heptopyranose.
GDP D-glycero-alpha-D-manno-Heptopyranose has been prepared in good overall yield from 2,3,4,6,7-penta-O-acetyl-D-glycero-D-manno-heptopyranose by a short-step synthesis. Phosphitylation using the phosphoramidite procedure afforded the alpha-anomer in high selectivity. Subsequent oxidation and partial deprotection gave the acetylated phosphate derivative, which was subjected to the coupling reaction with GMP-morpholidate to furnish the acetylated heptose nucleoside diphosphate in good yield. De-O-acetylation and final purification afforded the target GDP D-glycero-alpha-D-manno-heptopyranose, which serves as the substrate of the heptosyl transferase in Aneurinibacillus thermoaerophilus DSM 10155 and occurs as an intermediate in the biosynthesis of GDP 6-deoxy-heptose in Yersinia pseudotuberculosis.
Graziani
Andrea
A
Institute of Chemistry, University of Natural Resources and Applied Life Sciences, Muthgasse 18, A-1190 Vienna, Austria.
Zamyatina
Alla
A
Kosma
Paul
P
D000107:Acetylation; D001406:Bacillaceae / Q000378:metabolism; D011756:Diphosphates / Q000737:chemistry; D006023:Glycoproteins / Q000737:chemistry; D006153:Guanosine Diphosphate / Q000737:chemistry*; D006539:Heptoses / Q000138:chemical synthesis* / Q000737:chemistry; D008070:Lipopolysaccharides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009943:Organophosphorus Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D015011:Yersinia pseudotuberculosis / Q000378:metabolism
D011756:Diphosphates; D006023:Glycoproteins; D006539:Heptoses; D008070:Lipopolysaccharides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; C062615:glycero-alpha-manno-heptopyranose; D006153:Guanosine Diphosphate