215439-76-2Relevant academic research and scientific papers
Application of β-1,4-galactosyltransferase in the synthesis of complex branched-chain oligosaccharide mimics of fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14
Niggemann, Jutta,Kamerling, Johannis P.,Vliegenthart, Johannes F. G.
, p. 3011 - 3020 (1998)
The chemoenzymic synthesis is described of β-D-Galp-(1→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]- β-D-GlcpNAc-(1→O[CH2] 3O→4)-β-D-Glcp-(1→OCH2CH=CH2) 32 and β-D-Galp-(1→4)-β-D-GlcpNAc-(1→ O[CH2] 3O→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]- β-D-GlcpNAc-(1→O[CH2] 3O→4)-β-D-Glcp-(1→OCH2-CH=CH2) 33, representing hexa- and octasaccharide mimics of fragments of the Streptococcus pneumoniae type 14 polysaccharide. In a chemical approach the intermediate linear oligosaccharide mimics 30 and 31 were synthesized, wherein both terminal and non-terminal N-acetyl-β-D-glucosamine residues were not yet galactosylated. The alkyl-bridged derivatives were found to be good acceptor substrates for bovine milk β-1,4-galactosyltransferase. Reaction of the anomeric allyl functions with cysteamine under UV-irradiation gave the corresponding 3-(2-aminoethylthio)propyI glycosides 34 and 35, suitable for further coupling of the oligosaccharide mimics to protein carriers.
