Targeted allylation and propargylation of galactose-containing polysaccharides in water
2014 (English)In: Carbohydrate Polymers, ISSN 0144-8617, E-ISSN 1879-1344, Vol. 100, 46-54 p.Article in journal (Refereed) Published
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.
Polysaccharides, Spruce galactoglucomannan, Guar galactomannan, Tamarind xyloglucan, Allylation, Propargylation, Indium mediated, MALDI-TOF-MS
Chemical Sciences Polymer Technologies
IdentifiersURN: urn:nbn:se:kth:diva-141291DOI: 10.1016/j.carbpol.2012.11.053ISI: 000330092000008ScopusID: 2-s2.0-84887471490OAI: oai:DiVA.org:kth-141291DiVA: diva2:696199
FunderKnut and Alice Wallenberg Foundation
QC 201402132014-02-132014-02-132014-02-13Bibliographically approved