177280-23-8Relevant academic research and scientific papers
Synthesis of building blocks for an iterative approach towards oligomers of the Streptococcus pneumoniae type 1 zwitterionic capsular polysaccharide repeating unit
Ní Cheallaigh, Aisling,Oscarson, Stefan
, p. 940 - 960 (2016/11/17)
Zwitterionic capsular polysaccharide extracts, 8 kDa in mass, from Streptococcus pneumoniae type 1 (Spt1) have shown unique T-cell activating properties. Oligomers of the trisaccharide repeating unit of the Spt1 capsular polysaccharide [3)-4-NH2-α-d-QuipNAc-(14)-α-d-GalpA-(13)-α-d-GalpA-(1-]n of defined length are needed to further investigate this response. An approach towards iteratively extendable trisaccharide building blocks of the zwitterionic capsular polysaccharides of Spt1 is described. Key elements include the comparison of pre-glycosylation oxidation and post-glycosylation oxidation approaches using thioglycoside donors to the target trisaccharide, the optimisation of the post-glycosylation oxidation approach, and the conversion of the trisaccharide to building blocks tailored for iterative glycosylation. The construction and evaluation of stereotunable 2-N-3-O-oxazolidinone donors for the common bacterial 2-acetamido-4-amino-2,4,6-trideoxy-α-d-galactopyranoside motif is also described, as is a key intermediate for their efficient synthesis.
Synthesis of a Blocked Tetrasaccharide Related to the Repeating Unit of the Antigen from Shigella dysenteriae Type 9 in the Form of Its Methyl (R)-Pyruvate Ester and 2-(Trimethylsilyl)Ethyl Glycoside
Roy, Samarpita,Roy, Nirmolendu
, p. 521 - 535 (2007/10/03)
Starting from D-mannose, D-galactose and D-glucosamine hydrochloride, two disaccharide blocks were synthesized. Schmidt's inverse addition technique of tricbloroacetimidate was utilized for the construction of a disaccharide with a β-mannosidic linkage in
The synthesis of 16-mercaptohexadecanyl glycosides for biosensor applications
Kitov, Pavel I.,Railton, Craig,Bundle, David R.
, p. 361 - 369 (2007/10/03)
The p(k) trisaccharide and the central disaccharide element of asialo GM1 activated as their trichloroacetimidates were each used to glycosylate 16-(p-toluensulfonyloxy)hexadecanol 1. Displacement of the tosyl group by thiocyanate followed by s
Syntheses and insulin-like activity of phosphorylated galactose derivatives
Caro, Hugo-Norberto,Martin-Lomas, Manuel,Bernabe, Manuel
, p. 119 - 132 (2007/10/02)
The syntheses of the poly-phosphorylated galactosides 6,8,10,13,16, and 20, isolated as sodium salts, have been performed.The non-phosphorylated disaccharide 17 and trisaccharide 21 have been prepared via glycosylation of the 2-(trimethylsilyl)ethyl galac
