Mannich reaction of polysaccharides: Xylan functionalization in aqueous basic medium

•Xylan was modified using Mannich reaction in aqueous basic medium.•Increase in nitrogen content showed that modification was achieved.•Spectral analyses indicated that the reaction site was side chains oxygens.•Solution properties and thermal behavior of the modified xylan were changed.•Modified xy...

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Bibliographic Details
Published in:Carbohydrate polymers 2015-08, Vol.127, p.19-27
Main Authors: Ünlü, Cüneyt H., Kutlu, Meltem, Atıcı, Oya Galioğlu
Format: Article
Language:English
Subjects:
Aminomethylation
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antimicrobiality
Bacillus subtilis - drug effects
Bacillus subtilis - growth & development
Escherichia coli - drug effects
Escherichia coli - growth & development
Mannich reaction
Polysaccharide
Solutions
Structure-Activity Relationship
Water - chemistry
Xylan
Xylans - chemistry
Xylans - pharmacology
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Summary:•Xylan was modified using Mannich reaction in aqueous basic medium.•Increase in nitrogen content showed that modification was achieved.•Spectral analyses indicated that the reaction site was side chains oxygens.•Solution properties and thermal behavior of the modified xylan were changed.•Modified xylan had film formation ability while xylan had not. In this study modification of xylan via Mannich reaction in aqueous basic solution to obtain dimethylaminomethylated products and characterization of modified xylan were examined. Components were xylan (obtained from corn cob and used without modification) as active hydrogen containing compound, formaldehyde as carbonyl compound having no α-hydrogen and dimethylamine. Mannich reaction was used with different parameters such as component concentration, reaction temperature, and time. The highest modification was observed about 35°C with a nitrogen content of 4.6% by weight indicating successive modification. Both 1D and 2D NMR measurements displayed new signals related with aminomethyl groups. Spectral characterizations indicated that aminomethylation took place on oxygen sites. Moreover modified xylan could form film while xylan could not without an auxiliary agent. Antimicrobial activity tests indicated that modified xylan acted as a bacteriostatic material.
ISSN:0144-8617
1879-1344
DOI:10.1016/j.carbpol.2015.03.024