Acetyl Group Migration in Xylan and Glucan Model Compounds as Studied by Experimental and Computational Methods

Robert Lassfolk, Manuel Pedrón, Tomás Tejero, Pedro Merino, Johan Wärnå, Reko Leino

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)
43 Downloads (Pure)

Abstract

It was recently demonstrated by us that acetyl groups in oligosaccharides can migrate not only within one saccharide unit but also between two different saccharide units. Kinetics of this phenomenon were previously investigated in both mannan model compounds and a naturally occurring polysaccharide. In addition to mannans, there are also several other naturally acetylated polysaccharides, such as xyloglucans and xylans. Both xyloglucans and xylans are some of the most common acetylated polysaccharides in nature, displaying important roles in the plant cells. Considering the various biological roles of natural polysaccharides, it could be hypothesized that the intramolecular migration of acetyl groups might also be associated with regulation of the biological activity of polysaccharides in nature. Consequently, a better understanding of the overall migration phenomenon across the glycosidic bonds could help to understand the potential role of such migrations in the context of the biological activity of polysaccharides. Here, we present a detailed investigation on acetyl group migration in the synthesized xylan and glucan trisaccharide model compounds by a combination of experimental and computational methods, showing that the migration between the saccharide units proceeds from a secondary hydroxyl group of one saccharide unit toward a primary hydroxyl group of the other unit.

Original languageEnglish
Pages (from-to)14544-14554
JournalThe Journal of Organic Chemistry
Volume87
Issue number21
DOIs
Publication statusPublished - 4 Nov 2022
MoE publication typeA1 Journal article-refereed

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