Synthesis of the α-D-GlcpA-(1 → 3)-α-L-Rhap-(1 → 2)-L-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris

Ferenc Sajtos, János Hajkó, K. Kövér, A. Lipták

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-α-L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplén deacetylation of the trisaccharide 12 resulted in the 6″-OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1).

Original languageEnglish
Pages (from-to)253-259
Number of pages7
JournalCarbohydrate Research
Volume334
Issue number4
DOIs
Publication statusPublished - Sep 7 2001

Fingerprint

Chlorella vulgaris
Trisaccharides
Chlorophyta
Algae
Cell Wall
Cells
Derivatives
Ethyl Chloride
Glycosylation
Uronic Acids
Hydrogenolysis
Disaccharides
Chlorides

Keywords

  • α-D-Glucopyranuronosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-L-rhamnopyranose
  • Chlorella vulgaris
  • Hydrogenolysis
  • Oligosaccharide synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

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title = "Synthesis of the α-D-GlcpA-(1 → 3)-α-L-Rhap-(1 → 2)-L-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris",
abstract = "The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-α-L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zempl{\'e}n deacetylation of the trisaccharide 12 resulted in the 6″-OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1).",
keywords = "α-D-Glucopyranuronosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-L-rhamnopyranose, Chlorella vulgaris, Hydrogenolysis, Oligosaccharide synthesis",
author = "Ferenc Sajtos and J{\'a}nos Hajk{\'o} and K. K{\"o}v{\'e}r and A. Lipt{\'a}k",
year = "2001",
month = "9",
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T1 - Synthesis of the α-D-GlcpA-(1 → 3)-α-L-Rhap-(1 → 2)-L-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris

AU - Sajtos, Ferenc

AU - Hajkó, János

AU - Kövér, K.

AU - Lipták, A.

PY - 2001/9/7

Y1 - 2001/9/7

N2 - The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-α-L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplén deacetylation of the trisaccharide 12 resulted in the 6″-OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1).

AB - The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-α-L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplén deacetylation of the trisaccharide 12 resulted in the 6″-OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1).

KW - α-D-Glucopyranuronosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-L-rhamnopyranose

KW - Chlorella vulgaris

KW - Hydrogenolysis

KW - Oligosaccharide synthesis

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