628280-91-1Relevant academic research and scientific papers
Synthesis of a β-GlcN-(1→4)-MurNAc building block en route to N-deacetylated peptidoglycan fragments
Cirillo, Luigi,Bedini, Emiliano,Molinaro, Antonio,Parrilli, Michelangelo
scheme or table, p. 1117 - 1120 (2010/04/23)
Some bacteria present a variation in their peptidoglycan structure that is the absence of the N-acetyl substituent in the glucosamine residue. Very recently, this structural modification was demonstrated to be critical for host innate immune evasion in Listeria monocytogenes. To shed light on the molecular details of the evasion mechanism, the synthesis of some N-deacetylated peptidoglycan fragments is needed. En route to this goal a high-yielding synthesis of a GlcN-MurNAc disaccharide building block has been accomplished. A careful study of the optimal protecting groups and reaction conditions was done to have a complete β-stereoselectivity in glycosylation as well as to ensure a high versatility to the disaccharide building block.
Efficient preparation of three building blocks for the synthesis of heparan sulfate fragments: Towards the combinatorial synthesis of oligosaccharides from hypervariable regions
Gavard, Ollivier,Hersant, Yael,Alais, Jocelyne,Duverger, Veronique,Dilhas, Anna,Bascou, Alison,Bonnaffe, David
, p. 3603 - 3620 (2007/10/03)
New, multigram routes to suitably protected L-iduronyl monosaccharide donors 4 and 5 and 2-azidoglucose acceptors 6 and 7 are described. The L-iduronyl and D-glucuronyl disaccharides 1-3 were then prepared from these compounds, by means of efficient and regioselective protective group manipulations. These disaccharides form the basis of a combinatorial approach toward the synthesis of heparan sulfate fragments representative of the heterogeneous regions of this polysaccharide. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)Introduction.
