Change search
ReferencesLink to record
Permanent link

Direct link
Targeted allylation and propargylation of galactose-containing polysaccharides in water
KTH, School of Biotechnology (BIO), Glycoscience. KTH, School of Chemical Science and Engineering (CHE), Centres, Wallenberg Wood Science Center.
Show others and affiliations
2014 (English)In: Carbohydrate Polymers, ISSN 0144-8617, E-ISSN 1879-1344, Vol. 100, 46-54 p.Article in journal (Refereed) Published
Abstract [en]

Galactose units of spruce galactoglucomannan (GGM), guar galactomannan (GM), and tamarind (galacto)xyloglucan (XG) were selectively allylated. Firstly aldehyde functionalities were formed at the C-6 position via enzymatic oxidation by galactose oxidase. The formed aldehydes were further derivatized by an indium mediated Barbier-Grignard type reaction, resulting in the formation of homoallylic alcohols. In addition to allylic halides, the same reaction procedure was also applicable for GGM, when using propargyl bromide as halide. All reaction steps were done in water, thus the polysaccharides were modified in a one-pot reaction. The formation of the allylated, or propargylated, product was identified by MALDI-TOF-MS. All polysaccharide products were isolated and further characterized by GC-MS or NMR spectroscopy. By this chemo-enzymatic process, we have demonstrated a novel method for derivatization of GGM and other galactose-containing polysaccharides. The derivatized polysaccharides are potential platforms for further functionalizations.

Place, publisher, year, edition, pages
2014. Vol. 100, 46-54 p.
Keyword [en]
Polysaccharides, Spruce galactoglucomannan, Guar galactomannan, Tamarind xyloglucan, Allylation, Propargylation, Indium mediated, MALDI-TOF-MS
National Category
Chemical Sciences Polymer Technologies
URN: urn:nbn:se:kth:diva-141291DOI: 10.1016/j.carbpol.2012.11.053ISI: 000330092000008ScopusID: 2-s2.0-84887471490OAI: diva2:696199
Knut and Alice Wallenberg Foundation

QC 20140213

Available from: 2014-02-13 Created: 2014-02-13 Last updated: 2014-02-13Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full textScopus

Search in DiVA

By author/editor
Xu, ChunlinBrumer, Harry
By organisation
GlycoscienceWallenberg Wood Science Center
In the same journal
Carbohydrate Polymers
Chemical SciencesPolymer Technologies

Search outside of DiVA

GoogleGoogle Scholar
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

Altmetric score

Total: 19 hits
ReferencesLink to record
Permanent link

Direct link