Rapid synthesis of linear homologous oligoarabinofuranosides related to mycobacterial lipoarabinomannan and a neoglycoconjugate thereof

• Published in: Carbohydrate research Vol. 431; pp. 25 - 32
• Main Authors: Podvalnyy, Nikita M., Chizhov, Alexander O., Zinin, Alexander I., Kononov, Leonid O.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 05.08.2016; Elsevier
• Subjects: Arabinofuranose; Benzyl-free approach; Biochemistry & Molecular Biology; Chemistry; Chemistry, Applied; Chemistry, Organic; Glycoproteins; Life Sciences & Biomedicine; Lipoarabinomannan; Lipopolysaccharides - chemistry; Molecular Structure; Oligosaccharides - chemical synthesis; Oligosaccharides - chemistry; Physical Sciences; Polymerization; Polymerization of orthoesters; Science & Technology; Benzyl-free approach; Arabinofuranose; Polymerization of orthoesters; Lipoarabinomannan; 3-O-BENZYL-BETA-L-ARABINOFURANOSE 1,2,5-ORTHOPIVALATE; EFFICIENT SYNTHESIS; OLIGOSACCHARIDE; SQUARATE; HEXASACCHARIDE; ARABINOGALACTAN; FRAGMENTS; CELL-WALL; RING-OPENING POLYMERIZATION; ARABINOFURANOSYLATION
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2016.05.009

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.