Zeitschriftenartikel:
A. Zamyatina, S. Gronow, M. Puchberger, A. Graziani, A. Hofinger, P. Kosma:
"Efficient chemical synthesis of both anomers of ADP L-glycero- and D-glycero-D-manno-heptopyranose";
Carbohydrate Research,
338
(2003),
S. 2571
- 2589.
Kurzfassung englisch:
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-nanomers 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 ADPL-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-exchangechromatography and gel-filtration afforded ADP L- and D-glycero -β-D-manno-heptose in high yields.
Schlagworte:
Heptose; ADP heptose; Lipopolysaccharide; Sugar nucleotides; Sugar phosphates
"Offizielle" elektronische Version der Publikation (entsprechend ihrem Digital Object Identifier - DOI)
http://dx.doi.org/10.1016/S0008-6215(03)00319-7
Erstellt aus der Publikationsdatenbank der Technischen Universität Wien.