Acetyl group migration across the saccharide units in oligomannoside model compound

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http://hdl.handle.net/10138/308745

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Lassfolk , R , Rahkila , J , Johansson , M P , Ekholm , F S , Wärnå , J & Leino , R 2019 , ' Acetyl group migration across the saccharide units in oligomannoside model compound ' , Journal of the American Chemical Society , vol. 141 , no. 4 , pp. 1646-1654 . https://doi.org/10.1021/jacs.8b11563

Title: Acetyl group migration across the saccharide units in oligomannoside model compound
Author: Lassfolk, Robert; Rahkila, Jani; Johansson, Mikael Peter; Ekholm, Filip Sebastian; Wärnå, Johan; Leino, Reko
Contributor: University of Helsinki, Helsinki Institute of Sustainability Science (HELSUS)
University of Helsinki, Department of Chemistry
Date: 2019-01-30
Language: eng
Number of pages: 9
Belongs to series: Journal of the American Chemical Society
ISSN: 0002-7863
URI: http://hdl.handle.net/10138/308745
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.
Subject: ACYL
CELL-WALLS
FEATURES
GALACTOGLUCOMANNANS
GALACTOMANNANS
POLYSACCHARIDES
RESIDUES
SCREENING MODEL
SOLVATION
XYLOGLUCANS
116 Chemical sciences
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