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Synthesis of peptide-cellulose conjugate mediated by a soluble cellulose derivative having β-Ala esters (II): conjugates with O-phospho-l-serine-containing peptides

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Abstract

A synthetic route is described here for novel peptide-cellulose conjugates containing O-phospho-l-serine. First, Boc-Ser(PO3Ph2) and the related dipeptides, Boc-Ser(PO3Ph2)-Asp(OBzl) and Boc-Asp(OBzl)-Ser(PO3Ph2), were synthesized by adopting the phosphoryl-protection strategy. The condensation reaction between the α-carboxyl group of the protected Boc-Ser(PO3Ph2) and the β-amino groups of β-Ala-Cellulose using isobutyl chloroformate and N-methylmorpholine yielded the product conjugate, N β-[Boc-Ser(PO3Ph2)]-β-Ala-Cellulose. The degree of substitution of Boc-Ser(PO3Ph2) towards the β-amino groups of β-Ala-Cellulose was estimated as DS N = 0.75 (maximum, 1.0). Similar reactions between β-Ala-Cellulose and two kinds of protected dipeptides, Boc-Asp(OBzl)-Ser(PO3Ph2) and Boc-Ser(PO3Ph2)-Asp(OBzl), gave the corresponding conjugates, and the DS N was estimated to be 0.95 and 0.69, respectively. The phenyl, benzyl, and Boc groups were removed in one-pot using the Pt2O catalyst in 50 % trifluoroacetic acid/acetic acid. The 31P-NMR and UV-Visible spectra indicated the complete deprotection without any observable elimination of the phosphorylated peptides.

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Acknowledgments

This work was supported by Grants in Aid No. 22350103 and No. 23651083, and in part by the Grant in Aid for Global COE Program by the Ministry of Education, Culture, Sports, Science, and Technology, Japan. Part of this study was performed through the Program for Dissemination of Tenure-Track System funded by the Ministry of Education and Science, Japan. The corresponding author thanks to Prof. Dr. Tetsuya Fujimoto and Ms. Sachiko Yoshioka, Faculty of Textile Science and Technology, Shinshu University, Japan, for their kind instructions and operations for the quantitative 13C-NMR spectrum recording.

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Authors and Affiliations

  1. Faculty of Textile Science and Technology, Institute of High Polymer Research, Shinshu University, Tokida 3-15-1, Ueda, 386-8567, Japan

    Kesavan Devarayan & Kousaku Ohkawa

  2. Research Institute of Genome-based Biofactory, National Institute of Advanced Industrial Science and Technology (AIST), 2-17-2-1, Tsukisamu-higashi, Toyohira-ku, Sapporo, 062-8517, Japan

    Masakazu Hachisu

  3. Division of Chemistry and Materials, Faculty of Textile Science and Technology, Shinshu University, Tokida 3-15-1, Ueda, 386-8567, Japan

    Jun Araki

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  1. Kesavan Devarayan
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  2. Masakazu Hachisu
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  3. Jun Araki
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  4. Kousaku Ohkawa
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Correspondence to Kousaku Ohkawa.

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Devarayan, K., Hachisu, M., Araki, J. et al. Synthesis of peptide-cellulose conjugate mediated by a soluble cellulose derivative having β-Ala esters (II): conjugates with O-phospho-l-serine-containing peptides. Cellulose 20, 365–378 (2013). https://doi.org/10.1007/s10570-012-9822-1

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