Synthesis of the α-L-Araf-(1 → 2)-β-D-Galp-(1 → 6)-β-D-Galp-(1 → 6)-[α-L-Araf-(1 → 2)]-β-D-Galp-(1 → 6)-D-Gal hexasaccharide as a possible repeating unit of the cell-cultured exudates of Echinacea purpurea arabinogalactan

Magdolna Csávás, A. Borbás, Lóránt Jánossy, G. Batta, A. Lipták

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

For the characterization of the supposed epitope of an arabinogalactan, isolated from the extract of the cell-cultured Echinacea purpurea, the title hexasaccharide was synthesized. The whole synthetic route was based on the 6-O-(methoxydimethyl)methyl ether (MIP) protecting group strategy. 2-O-Benzyl-3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-β-D- galactopyranosyl-(1 → 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose was used to prepare the desired glycosyl donor and glycosyl acceptor both carrying a persistent O-benzyl group at position 2′. Reaction of the digalactose donor and the digalactose acceptor resulted in a β-(1 → 6)-linked galactose-containing tetrasaccharide in which OH-2′ and OH-2‴ were substituted with benzyl groups. Hydrogenolytic removal of the benzyl groups of the tetragalactose compound gave the diol aglycon which was diarabinosylated in one step to furnish the protected target compound, whose deprotection led to the title hexasaccharide. All of the synthesized compounds were characterized by 1H and 13C NMR spectra, as well as by MALDI-TOF mass-spectrometry measurements.

Original languageEnglish
Pages (from-to)107-115
Number of pages9
JournalCarbohydrate Research
Volume336
Issue number2
DOIs
Publication statusPublished - Nov 8 2001

Fingerprint

Echinacea
Exudates and Transudates
Galactose
Cultured Cells
Methyl Ethers
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry
Cell Extracts
Mass spectrometry
Epitopes
Mass Spectrometry
Nuclear magnetic resonance
propylene
hydroxide ion
arabinogalactan
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy

Keywords

  • Arabinogalactans
  • Branched-hexasaccharide
  • Echinacea purpurea
  • MIP ethers

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

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title = "Synthesis of the α-L-Araf-(1 → 2)-β-D-Galp-(1 → 6)-β-D-Galp-(1 → 6)-[α-L-Araf-(1 → 2)]-β-D-Galp-(1 → 6)-D-Gal hexasaccharide as a possible repeating unit of the cell-cultured exudates of Echinacea purpurea arabinogalactan",
abstract = "For the characterization of the supposed epitope of an arabinogalactan, isolated from the extract of the cell-cultured Echinacea purpurea, the title hexasaccharide was synthesized. The whole synthetic route was based on the 6-O-(methoxydimethyl)methyl ether (MIP) protecting group strategy. 2-O-Benzyl-3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-β-D- galactopyranosyl-(1 → 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose was used to prepare the desired glycosyl donor and glycosyl acceptor both carrying a persistent O-benzyl group at position 2′. Reaction of the digalactose donor and the digalactose acceptor resulted in a β-(1 → 6)-linked galactose-containing tetrasaccharide in which OH-2′ and OH-2‴ were substituted with benzyl groups. Hydrogenolytic removal of the benzyl groups of the tetragalactose compound gave the diol aglycon which was diarabinosylated in one step to furnish the protected target compound, whose deprotection led to the title hexasaccharide. All of the synthesized compounds were characterized by 1H and 13C NMR spectra, as well as by MALDI-TOF mass-spectrometry measurements.",
keywords = "Arabinogalactans, Branched-hexasaccharide, Echinacea purpurea, MIP ethers",
author = "Magdolna Cs{\'a}v{\'a}s and A. Borb{\'a}s and L{\'o}r{\'a}nt J{\'a}nossy and G. Batta and A. Lipt{\'a}k",
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T1 - Synthesis of the α-L-Araf-(1 → 2)-β-D-Galp-(1 → 6)-β-D-Galp-(1 → 6)-[α-L-Araf-(1 → 2)]-β-D-Galp-(1 → 6)-D-Gal hexasaccharide as a possible repeating unit of the cell-cultured exudates of Echinacea purpurea arabinogalactan

AU - Csávás, Magdolna

AU - Borbás, A.

AU - Jánossy, Lóránt

AU - Batta, G.

AU - Lipták, A.

PY - 2001/11/8

Y1 - 2001/11/8

N2 - For the characterization of the supposed epitope of an arabinogalactan, isolated from the extract of the cell-cultured Echinacea purpurea, the title hexasaccharide was synthesized. The whole synthetic route was based on the 6-O-(methoxydimethyl)methyl ether (MIP) protecting group strategy. 2-O-Benzyl-3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-β-D- galactopyranosyl-(1 → 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose was used to prepare the desired glycosyl donor and glycosyl acceptor both carrying a persistent O-benzyl group at position 2′. Reaction of the digalactose donor and the digalactose acceptor resulted in a β-(1 → 6)-linked galactose-containing tetrasaccharide in which OH-2′ and OH-2‴ were substituted with benzyl groups. Hydrogenolytic removal of the benzyl groups of the tetragalactose compound gave the diol aglycon which was diarabinosylated in one step to furnish the protected target compound, whose deprotection led to the title hexasaccharide. All of the synthesized compounds were characterized by 1H and 13C NMR spectra, as well as by MALDI-TOF mass-spectrometry measurements.

AB - For the characterization of the supposed epitope of an arabinogalactan, isolated from the extract of the cell-cultured Echinacea purpurea, the title hexasaccharide was synthesized. The whole synthetic route was based on the 6-O-(methoxydimethyl)methyl ether (MIP) protecting group strategy. 2-O-Benzyl-3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-β-D- galactopyranosyl-(1 → 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose was used to prepare the desired glycosyl donor and glycosyl acceptor both carrying a persistent O-benzyl group at position 2′. Reaction of the digalactose donor and the digalactose acceptor resulted in a β-(1 → 6)-linked galactose-containing tetrasaccharide in which OH-2′ and OH-2‴ were substituted with benzyl groups. Hydrogenolytic removal of the benzyl groups of the tetragalactose compound gave the diol aglycon which was diarabinosylated in one step to furnish the protected target compound, whose deprotection led to the title hexasaccharide. All of the synthesized compounds were characterized by 1H and 13C NMR spectra, as well as by MALDI-TOF mass-spectrometry measurements.

KW - Arabinogalactans

KW - Branched-hexasaccharide

KW - Echinacea purpurea

KW - MIP ethers

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