Trends in Glycoscience and Glycotechnology
Online ISSN : 1883-2113
Print ISSN : 0915-7352
ISSN-L : 0915-7352
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MINIREVIEW
  • Kohji Kitaguchi, Tomio Yabe
    2019 Volume 31 Issue 182 Pages E91-E97
    Published: July 25, 2019
    Released: July 25, 2019
    JOURNALS RESTRICTED ACCESS

    Pectin, a natural complex heteropolysaccharide, is a constituent of the cell wall and is conserved in all terrestrial plants. It is composed of galacturonic acid residues and a variety of neutral sugars such as rhamnose, galactose and arabinose. When one eats vegetables or fruits, pectin will be consumed, which will serve as dietary fiber in the body. Dietary fibers perform various physiological and metabolic functions in the human body. Pectin has also been reported to be involved in a number of physiological functions as a water-soluble dietary fiber. Many of them involve the work of secondary metabolites produced by intestinal bacteria as a dietary fiber when reaching the large intestine without being digested or absorbed in the human small intestine, and then further metabolized by intestinal bacteria. Besides the health benefits associated with dietary fibers, new health-related functions of pectin are being explored, particularly those related to the bioactive roles of inducing morphological changes in the small intestine. This review discusses the structure of pectin, its widely known physiological functions, and the possibility that pectin functions not only as a prebiotic but also as a physiologically active substance.

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  • Yoshiyuki Manabe
    2019 Volume 31 Issue 182 Pages E99-E108
    Published: July 25, 2019
    Released: July 25, 2019
    JOURNALS RESTRICTED ACCESS

    N-Glycans are glycans attached to asparagine residues in proteins via post-translational modification reactions. They have diverse structures, based on which they control protein functions. We chemically synthesized N-glycans to elucidate their molecular bases to exert functions. In this study, we synthesized a core fucose-containing dodecasaccharide and a bisecting GlcNAc-containing octasaccharide. Our N-glycan syntheses were characterized by practical preparation of fragments using microflow reactions and efficient construction of the N-glycan backbone through convergent synthetic routes. First, α-sialylation, β-mannosylation, and N-glycosylation were examined in a microflow system. While these reactions require strict control of reaction conditions, desired glycosylated products could be reproducibly obtained in large quantities using a microflow system. Furthermore, our convergent strategy of assembling synthetic fragments into desired oligosaccharide backbone structures allowed the successful syntheses of N-glycans in short steps. The key in this strategy was how to achieve a satisfactory level of efficiency in glycosylation between less reactive large fragments. We showed that amide groups (NHAc) form intermolecular hydrogen bonds to reduce the reactivity and found that the glycosylation reactivity could be markedly improved by protecting them as imides (NAc2). A high yield of the desired product could be achieved using an ether solvent for coordination stabilization of the intermediate cation even in otherwise poorly reactive glycosylation. In addition, we successfully improved stereoselectivity by carefully reviewing protection patterns.

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GLYCOTOPIC
MINIREVIEW (Jpn. Ed.)
  • Kohji Kitaguchi, Tomio Yabe
    2019 Volume 31 Issue 182 Pages J91-J97
    Published: July 25, 2019
    Released: July 25, 2019
    JOURNALS RESTRICTED ACCESS

    Pectin, a natural complex heteropolysaccharide, is a constituent of the cell wall and is conserved in all terrestrial plants. It is composed of galacturonic acid residues and a variety of neutral sugars such as rhamnose, galactose and arabinose. When one eats vegetables or fruits, pectin will be consumed, which will serve as dietary fiber in the body. Dietary fibers perform various physiological and metabolic functions in the human body. Pectin has also been reported to be involved in a number of physiological functions as a water-soluble dietary fiber. Many of them involve the work of secondary metabolites produced by intestinal bacteria as a dietary fiber when reaching the large intestine without being digested or absorbed in the human small intestine, and then further metabolized by intestinal bacteria. Besides the health benefits associated with dietary fibers, new health-related functions of pectin are being explored, particularly those related to the bioactive roles of inducing morphological changes in the small intestine. This review discusses the structure of pectin, its widely known physiological functions, and the possibility that pectin functions not only as a prebiotic but also as a physiologically active substance.

    Download PDF (2079K)
  • Yoshiyuki Manabe
    2019 Volume 31 Issue 182 Pages J99-J108
    Published: July 25, 2019
    Released: July 25, 2019
    JOURNALS RESTRICTED ACCESS

    N-Glycans are glycans attached to asparagine residues in proteins via post-translational modification reactions. They have diverse structures, based on which they control protein functions. We chemically synthesized N-glycans to elucidate their molecular bases to exert functions. In this study, we synthesized a core fucose-containing dodecasaccharide and a bisecting GlcNAc-containing octasaccharide. Our N-glycan syntheses were characterized by practical preparation of fragments using microflow reactions and efficient construction of the N-glycan backbone through convergent synthetic routes. First, α-sialylation, β-mannosylation, and N-glycosylation were examined in a microflow system. While these reactions require strict control of reaction conditions, desired glycosylated products could be reproducibly obtained in large quantities using a microflow system. Furthermore, our convergent strategy of assembling synthetic fragments into desired oligosaccharide backbone structures allowed the successful syntheses of N-glycans in short steps. The key in this strategy was how to achieve a satisfactory level of efficiency in glycosylation between less reactive large fragments. We showed that amide groups (NHAc) form intermolecular hydrogen bonds to reduce the reactivity and found that the glycosylation reactivity could be markedly improved by protecting them as imides (NAc2). A high yield of the desired product could be achieved using an ether solvent for coordination stabilization of the intermediate cation even in otherwise poorly reactive glycosylation. In addition, we successfully improved stereoselectivity by carefully reviewing protection patterns.

    Download PDF (1932K)
GLYCOTOPIC (Jpn. Ed.)
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