Synthesis of a deoxy analogue of ADP L-glycero-D-manno-heptose.
Starting from l-lyxose, indium-mediated chain elongation with allyl bromide followed by acetylation and oxidative cleavage of the double bond and deprotection afforded 2-deoxy-l-galacto-heptose as a 2-deoxy analogue of the bacterial carbohydrate l-glycero-d-manno-heptose in good overall yield. For the synthesis of the ADP-activated derivative, the 2-deoxy-heptose was O-acetylated and transformed into the anomeric bromide derivative, which was then converted into the acetylated heptopyranosyl phosphate by reaction with tetrabutylammonium phosphate. Deprotection and separation of the anomeric phosphates furnished 2-deoxy-beta-l-galacto-heptopyranosyl phosphate. Coupling of the acetylated heptosyl phosphate with AMP morpholidate afforded the acetylated ADP derivative in good yield. Removal of the acetyl groups gave the target compound ADP 2-deoxy-l-galacto-heptopyranose, which may serve as substrate analogue of bacterial ADP heptosyl transferases for biochemical and crystallographic studies.
Balla
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Department of Chemistry, University of Natural Resources and Applied Life Sciences, Muthgasse 18, A-1190 Vienna, Austria.
Zamyatina
Alla
A
Hofinger
Andreas
A
Kosma
Paul
P
D000244:Adenosine Diphosphate / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000737:chemistry; D017666:Deuterium Oxide / Q000737:chemistry; D006539:Heptoses / Q000138:chemical synthesis* / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009711:Nucleotides / Q000737:chemistry; D009844:Oligosaccharides / Q000737:chemistry; D013379:Substrate Specificity; D013403:Sugar Phosphates / Q000737:chemistry
D002241:Carbohydrates; D006539:Heptoses; D008070:Lipopolysaccharides; D009711:Nucleotides; D009844:Oligosaccharides; D013403:Sugar Phosphates; C020495:sedoheptulose 7-phosphate; C026312:glycero-manno-heptose; D000244:Adenosine Diphosphate; D017666:Deuterium Oxide