Unconventional Methyl Galactan Synthesized via the Thexyldimethylsilyl Intermediate: Preparation, Characterization, and Properties

Andreas Koschella; Kari Inngjerdingen; Berit S. Paulsen; Gordon A. Morris; Stephen E. Harding; Thomas Heinze

doi:10.1002/mabi.200700120

Unconventional Methyl Galactan Synthesized via the Thexyldimethylsilyl Intermediate: Preparation, Characterization, and Properties

Andreas Koschella, Kari Inngjerdingen, Berit S. Paulsen, Gordon A. Morris, Stephen E. Harding, Thomas Heinze

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

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)

Original language	English
Pages (from-to)	96-105
Number of pages	10
Journal	Macromolecular Bioscience
Volume	8
Issue number	1
Early online date	28 Sep 2007
DOIs	https://doi.org/10.1002/mabi.200700120
Publication status	Published - 9 Jan 2008
Externally published	Yes

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title = "Unconventional Methyl Galactan Synthesized via the Thexyldimethylsilyl Intermediate: Preparation, Characterization, and Properties",

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)",

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author = "Andreas Koschella and Kari Inngjerdingen and Paulsen, {Berit S.} and Morris, {Gordon A.} and Harding, {Stephen E.} and Thomas Heinze",

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T1 - Unconventional Methyl Galactan Synthesized via the Thexyldimethylsilyl Intermediate

T2 - Preparation, Characterization, and Properties

AU - Koschella, Andreas

AU - Inngjerdingen, Kari

AU - Paulsen, Berit S.

AU - Morris, Gordon A.

AU - Harding, Stephen E.

AU - Heinze, Thomas

PY - 2008/1/9

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N2 - 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)

AB - 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)

KW - β-(1 → 4) galactan

KW - Biological activity

KW - Biopolymers

KW - NMR

KW - Thexyldimethylsilyl ether

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Unconventional Methyl Galactan Synthesized via the Thexyldimethylsilyl Intermediate: Preparation, Characterization, and Properties

Abstract

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