Synthesis of the Non Reducing End Oligosaccharides of Glycosphingolipids from Ascaris suum

Autor:	Kimiaki Yamano, Naohiro Oshima, Yuna Umeda, Hiromi Kumada, Frank Schweizer, Fumiyuki Kiuchi, Noriyasu Hada, Tadahiro Takeda, Yoshinori Shimazaki
Rok vydání:	2019
Předmět:	chemistry.chemical_classification biology Chemistry Stereochemistry General Chemistry General Medicine Glycosphingolipid Oligosaccharide biology.organism_classification chemistry.chemical_compound Block (telecommunications) Biotinylation Drug Discovery Glycosyl Ascaris suum
Zdroj:	Chemical and Pharmaceutical Bulletin. 67:143-154
ISSN:	1347-5223 0009-2363
Popis:	Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from Ascaris suum have been accomplished. Galα1→3GalNAcβ1→OR (1), Galβ1→3Galα1→3GalNAcβ1→OR (2), Galβ1→6Galα1→3GalNAcβ1→OR (3), Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (4) and GlcNAcβ1→6Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (5) (R = biotinylated probe) were synthesized by stepwise condensation (1-4) and block synthesis (5) using 5-(methoxycarbonylpentyl) 2-O-benzoyl-3-O-2-napthylmethyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside (12) as a common precursor. Compound 12 was converted into two kinds of glycosyl acceptors and was condensed with suitable galactosyl donors, respectively.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::902e2aa10ec534f141a699338e87657c https://doi.org/10.1248/cpb.c18-00768 Zobrazit plný text záznamu