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Chien CY, Enomoto-Rogers Y, Takemura A, et al. Synthesis and characterization of regioselectively substituted curdlan hetero esters via an unexpected acyl migration. Carbohydr Polym. 2016;155:440-447doi: 10.1016/j.carbpol.2016.08.067.
Chien, C. Y., Enomoto-Rogers, Y., Takemura, A., & Iwata, T. (2017). Synthesis and characterization of regioselectively substituted curdlan hetero esters via an unexpected acyl migration. Carbohydrate polymers, 155440-447. https://doi.org/10.1016/j.carbpol.2016.08.067
Chien, Chih-Ying, et al. "Synthesis and characterization of regioselectively substituted curdlan hetero esters via an unexpected acyl migration." Carbohydrate polymers vol. 155 (2017): 440-447. doi: https://doi.org/10.1016/j.carbpol.2016.08.067
Chien CY, Enomoto-Rogers Y, Takemura A, Iwata T. Synthesis and characterization of regioselectively substituted curdlan hetero esters via an unexpected acyl migration. Carbohydr Polym. 2017 Jan 02;155:440-447. doi: 10.1016/j.carbpol.2016.08.067. Epub 2016 Aug 30. PMID: 27702533.
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Carbohydr Polym. 2017 Jan 02;155:440-447. doi: 10.1016/j.carbpol.2016.08.067. Epub 2016 Aug 30.

Synthesis and characterization of regioselectively substituted curdlan hetero esters via an unexpected acyl migration.

Carbohydrate polymers

Chih-Ying Chien, Yukiko Enomoto-Rogers, Akio Takemura, Tadahisa Iwata

Affiliations

  1. Science of Polymeric Materials, Department of Biomaterial Sciences, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan. Electronic address: [email protected].
  2. Science of Polymeric Materials, Department of Biomaterial Sciences, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan; Structural Materials Research Institute, National Institute of Advanced Industrial Science and Technology, 2266-98, Anagahora, Shimoshidami, Moriyama-ku, Nagoya, Aichi 463-8560 Japan. Electronic address: [email protected].
  3. Science of Polymeric Materials, Department of Biomaterial Sciences, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan. Electronic address: [email protected].
  4. Science of Polymeric Materials, Department of Biomaterial Sciences, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan. Electronic address: [email protected].

PMID: 27702533 DOI: 10.1016/j.carbpol.2016.08.067

Abstract

Regioselectively substituted curdlan esters were synthesized by protecting the C6 primary hydroxyl group with a triphenylmethyl group followed by the acylation of the secondary hydroxyl groups at C2 and C4. The subsequent detritylation of C6 trityl group under acidic conditions revealed an unexpected acyl migration from C4 to C6. This unique acyl migration in curdlan was first observed, which haven't been reported in other polysaccharides such as cellulose. The rate of this migration was found to be dependent on the length of the acyl group, leading to the proposal of a new mechanism for this transformation. Based on these results, we synthesized 2,6-di-O-acetyl-4-O-propionyl-curdlan, which was fully characterized by

Copyright © 2016 Elsevier Ltd. All rights reserved.

Keywords: Acyl migration; Curdlan; Hetero ester; Regioselectively

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