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...

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Published inCarbohydrate research Vol. 431; pp. 25 - 32
Main Authors Podvalnyy, Nikita M., Chizhov, Alexander O., Zinin, Alexander I., Kononov, Leonid O.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.08.2016
Elsevier
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Summary: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. [Display omitted] •Linear oligoarabinofuranosides related to mycobacterial LAM were synthesized.•The key building block used is the product of polymerization of arabinose orthoester.•The obtained oligosaccharides were converted into a conjugate with BSA.
Bibliography:ObjectType-Article-1
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ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2016.05.009