TY - JOUR
T1 - Synthesis of the Non Reducing End Oligosaccharides of Glycosphingolipids from Ascaris suum
AU - Hada, Noriyasu
AU - Umeda, Yuna
AU - Kumada, Hiromi
AU - Shimazaki, Yoshinori
AU - Yamano, Kimiaki
AU - Schweizer, Frank
AU - Oshima, Naohiro
AU - Takeda, Tadahiro
AU - Kiuchi, Fumiyuki
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research (No. 25460131) and by Ministry of Education, Culture, Sports, Science and Technology (MEXT)-supported program for the strategic research foundation at private universities (centers of excellence for research) in “molecular nanotechnology for green innovation,” FY 2012–2016.
Funding Information:
Acknowledgments This work was supported by a Grant-in-Aid for Scientific Research (No. 25460131) and by Ministry of Education, Culture, Sports, Science and Technology (MEXT)-supported program for the strategic research foundation at private universities (centers of excellence for research) in “molecular nanotechnology for green innovation,” FY 2012–2016.
Publisher Copyright:
© 2019 The Pharmaceutical Society of Japan.
PY - 2019
Y1 - 2019
N2 - 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=bioti-nylated probe) were synthesized by stepwise condensation (1–4) and block synthesis (5) using 5-(methoxycar-bonylpentyl) 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.
AB - 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=bioti-nylated probe) were synthesized by stepwise condensation (1–4) and block synthesis (5) using 5-(methoxycar-bonylpentyl) 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.
KW - Ascaris suum
KW - Biotin probe
KW - Glycosphingolipid
KW - Host–parasite interaction
KW - Stereocontrolled synthesis
UR - http://www.scopus.com/inward/record.url?scp=85061050885&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85061050885&partnerID=8YFLogxK
U2 - 10.1248/cpb.c18-00768
DO - 10.1248/cpb.c18-00768
M3 - Article
C2 - 30713275
AN - SCOPUS:85061050885
SN - 0009-2363
VL - 67
SP - 143
EP - 154
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 2
ER -