Rapid synthesis of linear homologous oligoarabinofuranosides related to mycobacterial lipoarabinomannan and a neoglycoconjugate thereof.
Rapid and simple synthesis of oligosaccharides related to one of the terminal motifs of mycobacterial lipoarabinomannan is described. An array of homologous linear α(1 → 5)-linked oligoarabinofuranosides with 4-(2-chloroethoxy)phenyl aglycon and selectively unprotected 5-OH group at the non-reducing end was obtained by oligomerization of 3-O-benzoyl β-D-arabinofuranose 1,2,5-orthobenzoate. Subsequent introduction of β(1 → 2)-linked arabinofuranose disaccharide moiety by step-wise glycosylation furnished the target oligosaccharides which were conjugated with bovine serum albumin.
N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp., 47, 119991, Moscow, Russian Federation.
Nikita M
NM
Podvalnyy
N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp., 47, 119991, Moscow, Russian Federation.
Alexander O
AO
Chizhov
N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp., 47, 119991, Moscow, Russian Federation.
Alexander I
AI
Zinin
N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp., 47, 119991, Moscow, Russian Federation. Electronic address: kononov@ioc.ac.ru.
Leonid O
LO
Kononov
D006023:Glycoproteins; D008070:Lipopolysaccharides / Q000737:chemistry*; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D058105:Polymerization
D006023:Glycoproteins; D008070:Lipopolysaccharides; D009844:Oligosaccharides; C050016:lipoarabinomannan
Arabinofuranose; Benzyl-free approach; Lipoarabinomannan; Polymerization of orthoesters