Trends in Glycoscience and Glycotechnology
Online ISSN : 1883-2113
Print ISSN : 0915-7352
ISSN-L : 0915-7352
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Volume 22, Issue 123
Displaying 1-6 of 6 articles from this issue
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MINIREVIEW
  • Double Diastereoselection, Regioselectivity, and the Importance of Donor-Acceptor Complementarity in the Stereoselectivity of Glycosylation Reactions
    Luis Bohé, David Crich
    Article type: MINIREVIEW
    2010 Volume 22 Issue 123 Pages 1-15
    Published: 2010
    Released on J-STAGE: June 10, 2010
    DOIhttps://doi.org/10.4052/tigg.22.1
    JOURNAL FREE ACCESS
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    Glycosylation is a process involving the union of two chiral partners, a donor and an acceptor, and is therefore formally subject to double diastereodifferentiation.In this review, we discuss, through the presentation of suitable examples, double diastereoselection in glycosylation reactions based on the “matched and mismatched concept”. We also discuss the related but more widely appreciated concept of regioselective glycosylation of diols and illustrate through select examples how this may vary on the basis of donor and even promoter.Finally, we diverge from the usual course of representation of glycosylation stereoselectivity as a simple ratio, and also represent it in terms of diastereomeric excess to facilitate comparison with other branches of organic chemistry.
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  • Chemical Biology of Glycoside-Type Bioactive Substances Controlling Nyctinastic Movement in Leguminous Plants
    Yoshiyuki Manabe, Sho Inomata, Minoru Ueda
    Article type: MINIREVIEW
    2010 Volume 22 Issue 123 Pages 16-25
    Published: 2010
    Released on J-STAGE: June 10, 2010
    DOIhttps://doi.org/10.4052/tigg.22.16
    JOURNAL FREE ACCESS
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    Leguminous plants open their leaves during the day and close them at night as if sleeping, a type of movement that follows circadian rhythms and is known as nyctinastic movement. This phenomenon is controlled by two endogenous bioactive substances that exhibit opposing activities: Leaf-Opening Factor (LOF), which opens the leaves, and Leaf-Closing Factor (LCF), which closes them. The authors have carried out chemical biological research using these bioactive substances in order to clarify the mechanisms of nyctinastic movement. Here, we report on the detection and identification of the target proteins of these compounds using original methodology.
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  • Stereocontrolled Construction of 1,2-cis-α-Glycosidic Linkages Using Glycosyl Diphenyl Phosphates and Synthesis of α-Galactosylceramide KRN7000
    Hisanori Nambu, Seiichi Nakamura, Noritoshi Suzuki, Shunichi Hashimoto
    Article type: MINIREVIEW
    2010 Volume 22 Issue 123 Pages 26-40
    Published: 2010
    Released on J-STAGE: June 10, 2010
    DOIhttps://doi.org/10.4052/tigg.22.26
    JOURNAL FREE ACCESS
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    The development of a general stereoselective method for 1,2-cis-α-glycosidations remains an important issue for synthesis in carbohydrate chemistry. Recently, we have achieved a highly stereocontrolled construction of 1,2-cis-α-glycosidic linkages using glycosyl diphenyl phosphates as glycosyl donors. The per-O-benzyl-protected glucosyl and galactosyl donors and the 3,4,6-tri-O-acetyl-2-azido-2-deoxygalactosyl donor each react with a range of acceptor alcohols in the presence of 0.05–0.2 equiv of HClO4 in dioxane/Et2O (1:1) to afford glycosides in good yields with good to high α-selectivities. The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of the α-galactosylceramide KRN7000, an activator of natural killer (NK) T cells through CD1d molecules.
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