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Targeted allylation...
Targeted allylation and propargylation of galactose-containing polysaccharides in water
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Leppänen, Ann-Sofie (author)
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- Xu, Chunlin (author)
- KTH,Glykovetenskap,Wallenberg Wood Science Center
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Parikka, Kirsti (author)
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Eklund, Patrik (author)
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Sjöholm, Rainer (author)
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- Brumer, Harry (author)
- KTH,Glykovetenskap,Wallenberg Wood Science Center
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Tenkanen, Maija (author)
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Willför, Stefan (author)
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(creator_code:org_t)
- Elsevier BV, 2014
- 2014
- English.
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In: Carbohydrate Polymers. - : Elsevier BV. - 0144-8617 .- 1879-1344. ; 100, s. 46-54
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
- TEKNIK OCH TEKNOLOGIER -- Kemiteknik -- Polymerteknologi (hsv//swe)
- ENGINEERING AND TECHNOLOGY -- Chemical Engineering -- Polymer Technologies (hsv//eng)
Keyword
- Polysaccharides
- Spruce galactoglucomannan
- Guar galactomannan
- Tamarind xyloglucan
- Allylation
- Propargylation
- Indium mediated
- MALDI-TOF-MS
Publication and Content Type
- ref (subject category)
- art (subject category)
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