Scope and limitation of the application of the (methoxydimethyl)methyl group in the synthesis of 2'-O-, 6'-O- and 2',6'-di-O-(α-L-arabinofuranosyl)-β-D-galactopyranosyl-(1→6)-D-galactoses

A. Borbás, Lóránt Jánossy, A. Lipták

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

For the characterisation of the anticipated epitope of an arabinogalactan, isolated from the extract of Echinacea purpurea, the trisaccharide α-L-Araf-(1→2)-β-D-Galp-(1→6)-D-Gal was synthesized. The easily available 3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-β-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose having the OH-2' free served as aglycone upon direct arabinosylation at the 2' position under Helferich conditions. The formed HgBr2 cleaved the acid sensitive protecting group at position 6', but under basic conditions the desired, fully protected trisaccharide, or its symmetrical dimerization derivative linked 6'- to 6'-position via an isopropylidene bridge, could be obtained. An alternative route involved arabinosylation of a hepta-O-acetylated digalactose with free OH-2'. Two other oligosaccharides, namely, α-L-Araf-(1→6)-β-D-Galp-(1→6)-D-Gal and (α-L-Araf)2-(1→2,6)-β-D-Galp-(1→6)-D-Gal were also synthesized and characterised. Copyright (C) 1999 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)98-109
Number of pages12
JournalCarbohydrate Research
Volume318
Issue number1-4
DOIs
Publication statusPublished - May 31 1999

Fingerprint

Galactose
Trisaccharides
Echinacea
Dimerization
Oligosaccharides
Epitopes
Derivatives
Acids
propylene
hydroxide ion

Keywords

  • (Methoxydimethyl)methyl ethers
  • Arabinogalactans
  • Dimerization
  • Echinacea purpurea
  • Oligosaccharides

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

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title = "Scope and limitation of the application of the (methoxydimethyl)methyl group in the synthesis of 2'-O-, 6'-O- and 2',6'-di-O-(α-L-arabinofuranosyl)-β-D-galactopyranosyl-(1→6)-D-galactoses",
abstract = "For the characterisation of the anticipated epitope of an arabinogalactan, isolated from the extract of Echinacea purpurea, the trisaccharide α-L-Araf-(1→2)-β-D-Galp-(1→6)-D-Gal was synthesized. The easily available 3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-β-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose having the OH-2' free served as aglycone upon direct arabinosylation at the 2' position under Helferich conditions. The formed HgBr2 cleaved the acid sensitive protecting group at position 6', but under basic conditions the desired, fully protected trisaccharide, or its symmetrical dimerization derivative linked 6'- to 6'-position via an isopropylidene bridge, could be obtained. An alternative route involved arabinosylation of a hepta-O-acetylated digalactose with free OH-2'. Two other oligosaccharides, namely, α-L-Araf-(1→6)-β-D-Galp-(1→6)-D-Gal and (α-L-Araf)2-(1→2,6)-β-D-Galp-(1→6)-D-Gal were also synthesized and characterised. Copyright (C) 1999 Elsevier Science Ltd.",
keywords = "(Methoxydimethyl)methyl ethers, Arabinogalactans, Dimerization, Echinacea purpurea, Oligosaccharides",
author = "A. Borb{\'a}s and L{\'o}r{\'a}nt J{\'a}nossy and A. Lipt{\'a}k",
year = "1999",
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T1 - Scope and limitation of the application of the (methoxydimethyl)methyl group in the synthesis of 2'-O-, 6'-O- and 2',6'-di-O-(α-L-arabinofuranosyl)-β-D-galactopyranosyl-(1→6)-D-galactoses

AU - Borbás, A.

AU - Jánossy, Lóránt

AU - Lipták, A.

PY - 1999/5/31

Y1 - 1999/5/31

N2 - For the characterisation of the anticipated epitope of an arabinogalactan, isolated from the extract of Echinacea purpurea, the trisaccharide α-L-Araf-(1→2)-β-D-Galp-(1→6)-D-Gal was synthesized. The easily available 3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-β-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose having the OH-2' free served as aglycone upon direct arabinosylation at the 2' position under Helferich conditions. The formed HgBr2 cleaved the acid sensitive protecting group at position 6', but under basic conditions the desired, fully protected trisaccharide, or its symmetrical dimerization derivative linked 6'- to 6'-position via an isopropylidene bridge, could be obtained. An alternative route involved arabinosylation of a hepta-O-acetylated digalactose with free OH-2'. Two other oligosaccharides, namely, α-L-Araf-(1→6)-β-D-Galp-(1→6)-D-Gal and (α-L-Araf)2-(1→2,6)-β-D-Galp-(1→6)-D-Gal were also synthesized and characterised. Copyright (C) 1999 Elsevier Science Ltd.

AB - For the characterisation of the anticipated epitope of an arabinogalactan, isolated from the extract of Echinacea purpurea, the trisaccharide α-L-Araf-(1→2)-β-D-Galp-(1→6)-D-Gal was synthesized. The easily available 3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-β-D-galactopyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose having the OH-2' free served as aglycone upon direct arabinosylation at the 2' position under Helferich conditions. The formed HgBr2 cleaved the acid sensitive protecting group at position 6', but under basic conditions the desired, fully protected trisaccharide, or its symmetrical dimerization derivative linked 6'- to 6'-position via an isopropylidene bridge, could be obtained. An alternative route involved arabinosylation of a hepta-O-acetylated digalactose with free OH-2'. Two other oligosaccharides, namely, α-L-Araf-(1→6)-β-D-Galp-(1→6)-D-Gal and (α-L-Araf)2-(1→2,6)-β-D-Galp-(1→6)-D-Gal were also synthesized and characterised. Copyright (C) 1999 Elsevier Science Ltd.

KW - (Methoxydimethyl)methyl ethers

KW - Arabinogalactans

KW - Dimerization

KW - Echinacea purpurea

KW - Oligosaccharides

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