117606-88-9Relevant academic research and scientific papers
Synthesis of E. faecium wall teichoic acid fragments
van der Es, Daan,Groenia, Nadia A.,Laverde, Diana,Overkleeft, Herman S.,Huebner, Johannes,van der Marel, Gijsbert A.,Codée, Jeroen D.C.
, p. 3893 - 3907 (2016/08/04)
The first synthesis of different Enterococcus faecium wall teichoic acid (WTA) fragments is presented. The structure of these major cell wall components was elucidated recently and it was shown that these glycerolphosphate (GroP) based polymers are built up from -6-(GalNAc-α(1–3)-GalNAc-β(1–2)-GroP)- repeating units. We assembled WTA fragments up to three repeating units in length, in two series that differ in the stereochemistry of the glycerolphosphate moiety. The key GalNAc-GalNAc-GroP synthons, required for the synthesis, were generated from galactosazide building blocks that were employed in highly stereoselective glycosylation reactions to furnish both the α- and β-configured linkages. By comparing the NMR spectra of the synthesized fragments with the isolated material it appears that the hereto undefined stereochemistry of the glycerol phosphate moiety is sn-glycerol-3-phosphate. The generated fragments will be valuable tools to study their immunological activity at the molecular level.
The Chemistry of L-Ascorbic and D-Isoascorbic Acids. 2. R and S Glyceraldehydes from a Common Intermediate
Mikkilineni, Amarendra B.,Kumar, Praveen,Abushanab, Elie
, p. 6005 - 6009 (2007/10/02)
(R)- and (S)-glyceraldehyde and glycerol derivatives have been prepared from (2R,3S)-1,2-O-isopropylidenebutane-1,2,3,4-tetrol. (2R,3S)- and (2S,3S)-1,2-O-benzylidenebutane-1,2,3,4-tetrol have been prepared and cleaved to give (R)- and (S)-1,2-O-benzylideneglyceraldehydes and -glycerols.The conservation of chirality and conversion to PAF analogues are also demonstrated.
