651731-26-9Relevant academic research and scientific papers
The mechanism of the reaction catalyzed by ADP-β-L-glycero-D-manno- heptose 6-epimerase
Read, Jay A.,Ahmed, Raef A.,Morrison, James P.,Coleman Jr., William G.,Tanner, Martin E.
, p. 8878 - 8879 (2007/10/03)
ADP-L-glycero-D-manno-heptose 6-epimerase (AGME, RfaD) is a bacterial enzyme that is involved in lipopolysaccharide biosynthesis and interconverts ADP-β-L-glycero-D-manno-heptose (ADP-L,D-Hep) with ADP-β-D-glycero-D-manno-heptose (ADP-D,D-Hep). AGME is kn
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.
