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Download fileAcetyl Group Migration across the Saccharide Units in Oligomannoside Model Compound
journal contribution
posted on 2018-12-26, 00:00 authored by Robert Lassfolk, Jani Rahkila, Mikael P. Johansson, Filip S. Ekholm, Johan Wärnå, Reko LeinoAcetylated
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.