TY - JOUR
T1 - Syntheses of model compounds related to an antigenic epitope in pectic polysaccharides from Bupleurum falcatum L.
AU - Hada, Noriyasu
AU - Ogino, Tomoko
AU - Yamada, Haruki
AU - Takeda, Tadahiro
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research (No. 12672062) from the Ministry of Education, Science, Sports and Culture of Japan. We gratefully acknowledge the financial support of Uehara Memorial Foundation. The authors are grateful to Mrs J. Hada for providing NMR and MS data.
PY - 2001/8/3
Y1 - 2001/8/3
N2 - Stereocontrolled syntheses of model compounds related to a category of the major antigenic epitope against anti-bupleurum 2IIc/PG-1-IgG from an anti-ulcer pectic polysaccharide are described. Glycosylation of the glucuronic acid donors methyl(2,3-di-O-benzoyl-4-O-methyl-α-D-glucopyranosyl trichloroacetimidate)uronate and methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate-(1 → 6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate with the common acceptor 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside in the presence of trimethylsilyl triflate (TMSOTf) gave the desired di- and trisaccharide derivatives. Furthermore the products were transformed into the oligo-valent clustering saccharides, N,N′,N″-tri-{5-[4-O-methyl-β-D-glucopyranosyluronic acid-(1 → 6)-β-D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5- benzenetriamide and N,N′,N″-tri-{5-[4-O-methyl-β-D-glucopyranosyluronic acid (1 → 6)-β-D-galactopyranosyl-(1 → 6)-β-D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5- benzenetriamide.
AB - Stereocontrolled syntheses of model compounds related to a category of the major antigenic epitope against anti-bupleurum 2IIc/PG-1-IgG from an anti-ulcer pectic polysaccharide are described. Glycosylation of the glucuronic acid donors methyl(2,3-di-O-benzoyl-4-O-methyl-α-D-glucopyranosyl trichloroacetimidate)uronate and methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate-(1 → 6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate with the common acceptor 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside in the presence of trimethylsilyl triflate (TMSOTf) gave the desired di- and trisaccharide derivatives. Furthermore the products were transformed into the oligo-valent clustering saccharides, N,N′,N″-tri-{5-[4-O-methyl-β-D-glucopyranosyluronic acid-(1 → 6)-β-D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5- benzenetriamide and N,N′,N″-tri-{5-[4-O-methyl-β-D-glucopyranosyluronic acid (1 → 6)-β-D-galactopyranosyl-(1 → 6)-β-D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5- benzenetriamide.
KW - Anti-ulcer pectic polysaccharide
KW - Antigenic epitope
KW - Bupleurum falcatum
KW - Chemical synthesis
KW - Oligovalent di- and trisaccharides
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UR - http://www.scopus.com/inward/citedby.url?scp=0035800704&partnerID=8YFLogxK
U2 - 10.1016/S0008-6215(01)00148-3
DO - 10.1016/S0008-6215(01)00148-3
M3 - Article
C2 - 11470246
AN - SCOPUS:0035800704
SN - 0008-6215
VL - 334
SP - 7
EP - 17
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 1
ER -