Acetyl group migration across the saccharide units in oligomannoside model compound

Robert Lassfolk, Jani Rahkila, Mikael Peter Johansson, Filip Sebastian Ekholm, Johan Wärnå, Reko Leino

Research output: Contribution to journalArticleScientificpeer-review

Abstract

Acetylated oligosaccharides are common in nature. While they are involved in several biochemical and biological processes, the role of the acetyl groups and the complexity of their migration has largely gone unnoticed. In this work, by combination of organic synthesis, NMR spectroscopy and quantum chemical modeling, we show that acetyl group migration is a much more complex phenomenon than previously known. By use of synthetic oligomannoside model compounds, we demonstrate, for the first time, that the migration of acetyl groups in oligosaccharides and polysaccharides may not be limited to transfer within a single monosaccharide moiety, but may also involve migration over a glycosidic bond between two different saccharide units. The observed phenomenon is not only interesting from the chemical point of view, but it also raises new questions about the potential biological role of acylated carbohydrates in nature.

LanguageEnglish
JournalJournal of the American Chemical Society
Volume141
Issue number4
Pages1646-1654
Number of pages9
ISSN0002-7863
DOIs
Publication statusPublished - 30 Jan 2019
MoE publication typeA1 Journal article-refereed

Fields of Science

  • ACYL
  • CELL-WALLS
  • FEATURES
  • GALACTOGLUCOMANNANS
  • GALACTOMANNANS
  • POLYSACCHARIDES
  • RESIDUES
  • SCREENING MODEL
  • SOLVATION
  • XYLOGLUCANS
  • 116 Chemical sciences

Cite this

Lassfolk, Robert ; Rahkila, Jani ; Johansson, Mikael Peter ; Ekholm, Filip Sebastian ; Wärnå, Johan ; Leino, Reko. / Acetyl group migration across the saccharide units in oligomannoside model compound. In: Journal of the American Chemical Society. 2019 ; Vol. 141, No. 4. pp. 1646-1654.
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abstract = "Acetylated oligosaccharides are common in nature. While they are involved in several biochemical and biological processes, the role of the acetyl groups and the complexity of their migration has largely gone unnoticed. In this work, by combination of organic synthesis, NMR spectroscopy and quantum chemical modeling, we show that acetyl group migration is a much more complex phenomenon than previously known. By use of synthetic oligomannoside model compounds, we demonstrate, for the first time, that the migration of acetyl groups in oligosaccharides and polysaccharides may not be limited to transfer within a single monosaccharide moiety, but may also involve migration over a glycosidic bond between two different saccharide units. The observed phenomenon is not only interesting from the chemical point of view, but it also raises new questions about the potential biological role of acylated carbohydrates in nature.",
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Acetyl group migration across the saccharide units in oligomannoside model compound. / Lassfolk, Robert ; Rahkila, Jani; Johansson, Mikael Peter; Ekholm, Filip Sebastian; Wärnå, Johan; Leino, Reko.

In: Journal of the American Chemical Society, Vol. 141, No. 4, 30.01.2019, p. 1646-1654.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Acetyl group migration across the saccharide units in oligomannoside model compound

AU - Lassfolk, Robert

AU - Rahkila, Jani

AU - Johansson, Mikael Peter

AU - Ekholm, Filip Sebastian

AU - Wärnå, Johan

AU - Leino, Reko

PY - 2019/1/30

Y1 - 2019/1/30

N2 - Acetylated oligosaccharides are common in nature. While they are involved in several biochemical and biological processes, the role of the acetyl groups and the complexity of their migration has largely gone unnoticed. In this work, by combination of organic synthesis, NMR spectroscopy and quantum chemical modeling, we show that acetyl group migration is a much more complex phenomenon than previously known. By use of synthetic oligomannoside model compounds, we demonstrate, for the first time, that the migration of acetyl groups in oligosaccharides and polysaccharides may not be limited to transfer within a single monosaccharide moiety, but may also involve migration over a glycosidic bond between two different saccharide units. The observed phenomenon is not only interesting from the chemical point of view, but it also raises new questions about the potential biological role of acylated carbohydrates in nature.

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