Syntheses of model compounds related to an antigenic epitope in pectic polysaccharides from Bupleurum falcatum L.

Noriyasu Hada, Tomoko Ogino, Haruki Yamada, Tadahiro Takeda

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7-17
Number of pages11
JournalCarbohydrate Research
Volume334
Issue number1
DOIs
Publication statusPublished - 2001 Aug 3

Fingerprint

Bupleurum
Polysaccharides
Epitopes
Glycosylation
Trisaccharides
Glucuronic Acid
Acids
Disaccharides
Galactose
Ulcer
Cluster Analysis
Derivatives
trichloroacetamide

Keywords

  • Anti-ulcer pectic polysaccharide
  • Antigenic epitope
  • Bupleurum falcatum
  • Chemical synthesis
  • Oligovalent di- and trisaccharides

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Syntheses of model compounds related to an antigenic epitope in pectic polysaccharides from Bupleurum falcatum L. / Hada, Noriyasu; Ogino, Tomoko; Yamada, Haruki; Takeda, Tadahiro.

In: Carbohydrate Research, Vol. 334, No. 1, 03.08.2001, p. 7-17.

Research output: Contribution to journalArticle

Hada, Noriyasu ; Ogino, Tomoko ; Yamada, Haruki ; Takeda, Tadahiro. / Syntheses of model compounds related to an antigenic epitope in pectic polysaccharides from Bupleurum falcatum L. In: Carbohydrate Research. 2001 ; Vol. 334, No. 1. pp. 7-17.
@article{5d89a3bc096d455ca078038b6132daab,
title = "Syntheses of model compounds related to an antigenic epitope in pectic polysaccharides from Bupleurum falcatum L.",
abstract = "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.",
keywords = "Anti-ulcer pectic polysaccharide, Antigenic epitope, Bupleurum falcatum, Chemical synthesis, Oligovalent di- and trisaccharides",
author = "Noriyasu Hada and Tomoko Ogino and Haruki Yamada and Tadahiro Takeda",
year = "2001",
month = "8",
day = "3",
doi = "10.1016/S0008-6215(01)00148-3",
language = "English",
volume = "334",
pages = "7--17",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier BV",
number = "1",

}

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

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

UR - http://www.scopus.com/inward/record.url?scp=0035800704&partnerID=8YFLogxK

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

VL - 334

SP - 7

EP - 17

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 1

ER -