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

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

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2016, Volume: 431, Pages: 25-32 Pages count : 8 DOI: 10.1016/j.carres.2016.05.009

Authors

Podvalnyy Nikita M. ¹ , Chizhov Alexander O. ¹ , Zinin Alexander I. ¹ , Kononov Leonid O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp., 47, 119991, Moscow, Russian Federation

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.

Podvalnyy N.M. , Chizhov A.O. , Zinin A.I. , Kononov L.O.
Rapid synthesis of linear homologous oligoarabinofuranosides related to mycobacterial lipoarabinomannan and a neoglycoconjugate thereof
Carbohydrate Research. 2016. V.431. P.25-32. DOI: 10.1016/j.carres.2016.05.009 WOS Scopus OpenAlex

Web of science:	WOS:000380680700004
Scopus:	2-s2.0-84971641012
OpenAlex:	W2395199608

DB	Citing
OpenAlex	22
Scopus	26
Web of science	25