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Unconventional methyl galactan synthesized via the thexyldimethylsilyl intermediate: Preparation, characterization, and properties

Koschella, A., Inngjerdingen, K., Paulsen, B. S., Morris, Gordon, Harding, S. E. and Heinze, T. (2008) Unconventional methyl galactan synthesized via the thexyldimethylsilyl intermediate: Preparation, characterization, and properties. Macromolecular Bioscience, 8 (1). pp. 96-105. ISSN 1616-5187

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Abstract

Reaction of a β-(1 → 4) linked galactan with TDMS chloride followed by methylation and desilylation yields methyl galactans with unconventional functionalization patterns. The products were characterized via FTIR and NMR of the intact polymer and by CE after controlled depolymerization. A TDMS-derivatized methyl galactan contains differently methylated secondary hydroxyl groups. SEC and analytical ultracentrifugation showed a consistent decrease in the molecular weight after the consecutive reaction steps. Biological studies revealed that the methyl galactans are less active in complement fixation assays as compared with a 3-O-methyl galactan-enriched polysaccharide fraction isolated from Acanthus ebracteatus. (Graph Presented) © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

Item Type: Article
Uncontrolled Keywords: β-(1 → 4) galactan Biological activity Biopolymers NMR Thexyldimethylsilyl ether Methyl galactan Ultracentrifugation Bioactivity Depolymerization Fourier transform infrared spectroscopy Molecular weight Nuclear magnetic resonance Ethers 3 o methylgalactan galactan methylgalactan polysaccharide unclassified drug Acanthus ebracteatus article carbohydrate synthesis desilylation fractionation infrared spectroscopy medicinal plant methylation nonhuman nuclear magnetic resonance spectroscopy Complement Fixation Tests Galactans Magnetic Resonance Spectroscopy Methylgalactosides Models, Molecular Molecular Structure Spectroscopy, Fourier Transform Infrared
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
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Language of Original Document: English
Correspondence Address: Heinze, T.; Center of Excellence for Polysaccharide Research, Friedrich Schiller University of Jena, Humboldtstrasse 10, D-07743 Jena, Germany; email: thomas.heinze@uni-jena.de
Chemicals/CAS: galactan, 39300-87-3, 9037-55-2; Galactans; Methylgalactosides
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Depositing User: Gordon Morris
Date Deposited: 13 May 2011 12:32
Last Modified: 01 Jul 2011 16:38
URI: http://eprints.hud.ac.uk/id/eprint/10446

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