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Brønsted acid-catalyzed ring-opening polycondensation of galactose-based cyclic sulfite

Polymer Journal volume 55, pages 213–221 (2023)Cite this article

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Abstract

We investigated the polymerization behavior of galactose-based cyclic sulfite as a monomer used to develop the graft polymerization preparation of (1 → 2)-galactan from an alcoholic aglycon. Galactose-based cyclic sulfite 6 was prepared from commercially available tri-O-acetyl-D-galactal in 5 steps. Treatment of 6 with catalytic (+)-10-camphorsulfonic acid (CSA) in the presence of water as the initiator exhibited ring-opening polycondensation of 6 to give benzylated (1 → 2)-galactan and complete elimination of SO2 from the main polymer chain. The MALDI-TOF mass spectrum of the obtained polymer showed a simple pattern with even intervals, which suggested formation of benzylated (1 → 2)-galactan with OH groups at both ends. When we used 4-penten-1-ol as the alcohol initiator for polycondensation of 6, we obtained a pentenoyl group-terminated polymer and/or cyclic oligosaccharides. The reaction mechanism for polycondensation of 6 was probed through systematic investigations of polymerization and DOSY spectral measurements of the polymer.

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Acknowledgements

This work was supported by the Ogasawara Toshiaki Memorial Foundation.

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Authors and Affiliations

  1. Department of Pharmaceutical Engineering, Faculty of Engineering, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan

    Ryo Miyazaki, Misaki Suzuki, Sangeetha Srinivasa Shetty, Taichi Shimazaki, Issey Osaka, Noriyuki Nakajima, Masahiro Hamada & Yasuhito Koyama

  2. Biotechnology Research Center, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan

    Issey Osaka, Noriyuki Nakajima, Masahiro Hamada & Yasuhito Koyama

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  1. Ryo Miyazaki
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Correspondence to Yasuhito Koyama.

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Miyazaki, R., Suzuki, M., Shetty, S.S. et al. Brønsted acid-catalyzed ring-opening polycondensation of galactose-based cyclic sulfite. Polym J 55, 213–221 (2023). https://doi.org/10.1038/s41428-022-00724-x

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