Stereo- and Regioselective Direct Multi-Deuterium-Labeling Methods for Sugars

Authors

  • Dr. Yoshinari Sawama,

    1. Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigakunishi, Gifu 501-1196 (Japan), Fax: (+81) 58-230-8109
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  • Yuki Yabe,

    1. Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigakunishi, Gifu 501-1196 (Japan), Fax: (+81) 58-230-8109
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  • Hiroki Iwata,

    1. Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigakunishi, Gifu 501-1196 (Japan), Fax: (+81) 58-230-8109
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  • Dr. Yuta Fujiwara,

    1. Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigakunishi, Gifu 501-1196 (Japan), Fax: (+81) 58-230-8109
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  • Dr. Yasunari Monguchi,

    1. Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigakunishi, Gifu 501-1196 (Japan), Fax: (+81) 58-230-8109
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  • Prof. Dr. Hironao Sajiki

    Corresponding author
    1. Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigakunishi, Gifu 501-1196 (Japan), Fax: (+81) 58-230-8109
    • Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigakunishi, Gifu 501-1196 (Japan), Fax: (+81) 58-230-8109===

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Abstract

Deuterium-labeled sugars can be utilized as powerful tools for the architectural analyses of high-sugar-containing molecules represented by the nucleic acids and glycoproteins, and chiral building blocks for the syntheses of new drug candidates (heavy drugs) due to their potential characteristics, such as simplifying the 1H NMR spectra and the stability of C[BOND]D bonds compared with C[BOND]H bonds. We have established a direct and efficient synthetic method of deuterated sugars from non-labeled sugars by using the heterogeneous Ru/C-catalyzed H–D exchange reaction in D2O under a hydrogen atmosphere with perfect chemo- and stereoselectivities. The direct H–D exchange reaction can selectively proceed on carbons adjacent to the free hydroxyl groups, and the deuterium labeling of various pyranosides (such as glucose and disaccharides), as well as furanosides, represented by ribose and deoxyribose was realized. Furthermore, the desired number of deuterium atoms can be freely incorporated into selected positions by the site-selective protection of the hydroxyl groups using acetal-type protective groups because the deuterium exchange reaction never proceeds on positions adjacent to the protected hydroxyl groups.

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