322640-32-4Relevant academic research and scientific papers
Efficient chemical synthesis of both anomers of ADP L-glycero- and D-glycero-D-manno-heptopyranose
Zamyatina, Alla,Gronow, Sabine,Puchberger, Michael,Graziani, Andrea,Hofinger, Andreas,Kosma, Paul
, p. 2571 - 2589 (2007/10/03)
A series of anomeric phosphates and ADP-activated L-glycero- and D-glycero-D-manno-heptopyranoses has been prepared in high overall yields, which provided model compounds and substrates in the elucidation of biosynthetic pathways and glycosyl transfer reactions of nucleotide-activated bacterial heptoses. The α-anomers of the heptosyl phosphates were obtained in high yield and selectivity using the phosphoramidite procedure, whereas the β-phosphates were formed preferentially employing acylation of reducing heptoses with diphenyl phosphorochloridate. An efficient route to the formation of the nucleotide diphosphate sugars was elaborated by coupling of the O-acetylated phosphates with AMP-morpholidate followed by alkaline deprotection to furnish ADP-L- and D-glycero-α-D-manno-heptose in 84 and 89% yield, respectively. Deacetylation of the O-acetylated β-configured ADP heptoses was conducted at strictly controlled conditions (-28°C at pH 10.5) to suppress formation of cyclic heptose-1,2-phosphodiesters with concomitant release of AMP. Isolation of the unstable β-configured ADP-heptoses by anion-exchange chromatography and gel-filtration afforded ADP L- and D-glycero-β-D-manno-heptose in high yields.
