5915-64-0Relevant articles and documents
Modular synthesis of diphospholipid oligosaccharide fragments of the bacterial cell wall and their use to study the mechanism of moenomycin and other antibiotics
Gampe, Christian M.,Tsukamoto, Hirokazu,Wang, Tsung-Shing Andrew,Walker, Suzanne,Kahne, Daniel
, p. 9771 - 9778 (2012/02/15)
We present a flexible, modular route to GlcNAc-MurNAc-oligosaccharides that can be readily converted into peptidoglycan (PG) fragments to serve as reagents for the study of bacterial enzymes that are targets for antibiotics. Demonstrating the utility of these synthetic PG substrates, we show that the tetrasaccharide substrate lipid IV (3), but not the disaccharide substrate lipid II (2), significantly increases the concentration of moenomycin A required to inhibit a prototypical PG-glycosyltransferase (PGT). These results imply that lipid IV and moenomycin A bind to the same site on the enzyme. We also show the moenomycin A inhibits the formation of elongated polysaccharide product but does not affect length distribution. We conclude that moenomycin A blocks PG-strand initiation rather than elongation or chain termination. Synthetic access to diphospholipid oligosaccharides will enable further studies of bacterial cell wall synthesis with the long-term goal of identifying novel antibiotics.
GENERAL METHOD OF STEREOSPECIFIC SYNTHESIS OF NATURAL POLYPRENOLS. SYNTHESIS OF BETULAPRENOL-6, -7, -8, AND -9
Sato, Kikumasa,Miyamoto, Osamu,Inoue, Seiichi,Furusawa, Fumio,Matsuhasi, Yasusuke
, p. 1105 - 1108 (2007/10/02)
A stereoselective synthesis of (Z,Z,Z)-12-benzyloxy-1-chloro-2,6,10-trimethyldodeca-2,6,10-triene was achieved starting from (Z,Z)-farnesol.All the components of betulaprenols were synthesized using the C15 block 3 and its lower homologue (C10 block) as t
SYNTHESIS OF (2Z,6Z,10Z,14E,18E)-FARNESYLFARNESOL
Moiseenkov, Alexander M.,Polunin, Evgeni V.,Semenovsky, Alexei V.
, p. 3309 - 3312 (2007/10/02)
Nine-step synthesis of the title triterpenol from (E,E)-farnesol using a two-stage cis-C5-homologation procedure is described.