TY - JOUR
T1 - Synthetic studies on glycosphingolipids from the parasite Echinococcus multilocularis
AU - Hada, Noriyasu
AU - Hayashi, Eriko
AU - Takeda, Tadahiro
N1 - Funding Information:
The authors would like to thank Miss T. Naito for performing the microanalyses at Nagoya City University, Nagoya, Japan. This work was supported by the Sasagawa Scientific Research Grant from The Japan Science Society and also supported by a Grant-in-Aid for Encouragement of Young Scientists, No. 70296531, from the Ministry of Education, Science, Sports and Culture of Japan.
PY - 1999/3/15
Y1 - 1999/3/15
N2 - Novel neutral glycosphingolipids isolated from the metacestodes of Echinococcus multilocularis by Persat, may be expected to be involved in host-parasite interactions. We have synthesized these glycosphingolipid analogues containing 2-branched fatty alkyl residues in place of ceramide. The glycosylation of galactosyl donors 4 and 5 with each of the acceptors 2 and 11 in the presence of N-iodosuccinimide (NIS)/TfOH, and the glycosylation of fucosyl donor 13 with acceptors 12 and 20 in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) gave the desired oligosaccharide derivatives at good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycosides 6, 15, 21, and 26 were converted to glycosylimidates 7, 16, 22, and 27, which were condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated give four target glycosphingolipid analogues. Copyright (C) 1999 Elsevier Science Ltd.
AB - Novel neutral glycosphingolipids isolated from the metacestodes of Echinococcus multilocularis by Persat, may be expected to be involved in host-parasite interactions. We have synthesized these glycosphingolipid analogues containing 2-branched fatty alkyl residues in place of ceramide. The glycosylation of galactosyl donors 4 and 5 with each of the acceptors 2 and 11 in the presence of N-iodosuccinimide (NIS)/TfOH, and the glycosylation of fucosyl donor 13 with acceptors 12 and 20 in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) gave the desired oligosaccharide derivatives at good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycosides 6, 15, 21, and 26 were converted to glycosylimidates 7, 16, 22, and 27, which were condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated give four target glycosphingolipid analogues. Copyright (C) 1999 Elsevier Science Ltd.
KW - Chemical synthesis
KW - Echinococcus mululocularis
KW - Glycosphingolipids
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U2 - 10.1016/S0008-6215(99)00027-0
DO - 10.1016/S0008-6215(99)00027-0
M3 - Article
C2 - 10420588
AN - SCOPUS:0033023474
SN - 0008-6215
VL - 316
SP - 58
EP - 70
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 1-4
ER -