Microwave-assisted heating reactions of N-acetylglucosamine (GlcNAc) in sulfolane as a method generating 1,6-anhydrosugars consisting of amino monosaccharide backbones

Harumi Kaga, Masaru Enomoto, Hiroki Shimizu, Izuru Nagashima, Keigo Matsuda, Seigou Kawaguchi, Atsushi Narumi

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The microwave-assisted heating reaction of N-acetyl glucosamine (GlcNAc) in sulfolane is described. The reaction produces two major products that are assignable to 1,6-anhydro-2-acetamido-2-deoxy-β-d-glucopyranose (AGPNAc) and 1,6-anhydro-2-acetamido-2-deoxy-β-d-glucofuranose (AGFNAc). In order to reveal a general feature of the system, the 3, 5, and 10 min reactions were performed at 140, 160, 180, 200, and 220 C to clarify the time course changes in the conversion of GlcNAc and the yields of the two produced 1,6-anhydrosugars. Temperature is a crucial factor that significantly affects the conversion of GlcNAc. The yields of AGPNAc and AGFNAc are also drastically changed depending on the reaction conditions. The 5-min reaction at 200 C is shown to be the optimal condition to generate the 1,6-anhydrosugars with a high efficiency in which AGPNAc and AGFNAc are produced in the yields of 21% and 44%, respectively. Consequently, the microwave-assisted heating reaction of GlcNAc in sulfolane is shown to be a simple and promising pathway to generate 1,6-anhydrosugars consisting of amino monosaccharide backbones, which have high potentials as raw materials leading to biological oligosaccharides and biomimetic polysaccharides.

    Original languageEnglish
    Article number1944
    JournalMolecules
    Volume25
    Issue number8
    DOIs
    Publication statusPublished - 2020 Apr

    Keywords

    • Anhydro-furanose
    • Anhydrosugar
    • Biologically active building block
    • Microwave
    • N-acetyl glucosamine (GlcNAc
    • NAG), anhydro-pyranose
    • Sulfolane

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Chemistry (miscellaneous)
    • Molecular Medicine
    • Pharmaceutical Science
    • Drug Discovery
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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