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Oxidation of Primary Alcohol Groups of Naturally Occurring Polysaccharides with 2,2,6,6-Tetramethyl-1-Piperidine Oxoammonium Ion
Abstract
The primary alcohol groups of ten polysaccharides, with widely different structures and water solubilities, were oxidized to carboxyl groups using 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion (TEMPO) at pH 10.8 and 0°C. The yield and selectivity for the primary alcohol group were high for all ten of the polysaccharides. The oxidation greatly increased the water-solubility of the polysaccharides. Water-insoluble polysaccharides such as amylose, cellulose, and chitin became water-soluble to the extent of approximately 10% (w/v). The water-soluble polysaccharides had their degree of solubility doubled or tripled. The specific optical rotation, viscosity, and gelling properties with calcium ion were determined. The oxidized polysaccharides are new anionic polymers with unique structures that could have application as gums, gels, and films.
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Citations
Cited by
Saito, T., & Isogai, A. (2004) · Biomacromolecules · doi:10.1021/bm0497769 · Cited by 1,292
Steric stabilization of a cellulose microcrystal suspension by poly(ethylene glycol) grafting
Araki, J., Wada, M., & Kuga, S. (2001) · Langmuir · doi:10.1021/la001070m · Cited by 720
Pharmaceutical significance of cellulose: A review
Kamel, S., Ali, N., Jahangir, K., Shah, S. M., & El-Gendy, A. A. (2008) · Express Polymer Letters · doi:10.3144/expresspolymlett.2008.90 · Cited by 465
Preparation of Polyuronic Acid from Cellulose by TEMPO-mediated Oxidation
Isogai, A., & Kato, Y. (1998) · Cellulose · doi:10.1023/a:1009208603673 · Cited by 437
Contact Lens Materials: A Materials Science Perspective
Musgrave, C. S. A., & Fang, F. (2019) · Materials · doi:10.3390/ma12020261 · Cited by 355
Metadata
- Authors
- Chang, P. S., & Robyt, J. F.
- Venue
- Journal of Carbohydrate Chemistry
- Publisher
- Informa UK Limited
- Published
- 1996-09
- Volume
- 15
- Issue
- 7
- Pages
- 819-830
- ISSN
- 0732-8303 (ISSN-L)
- 1532-2327
- OpenAlex
- W2078248040
- Cited by
- 189
- References
- 0
- FWCI
- 6.32
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Oxidation of Primary Alcohol Groups of Naturally Occurring Polysaccharides with 2,2,6,6-Tetramethyl-1-Piperidine Oxoammonium Ion. https://app.cochat.ai/papers/10.1080/07328309608005694
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- Chang, P. S., & Robyt, J. F. (1996). Oxidation of Primary Alcohol Groups of Naturally Occurring Polysaccharides with 2,2,6,6-Tetramethyl-1-Piperidine Oxoammonium Ion. Journal of Carbohydrate Chemistry. https://doi.org/10.1080/07328309608005694
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