Recent progress in the synthesis of glycosphingolipids

被引:4
作者
Ando, Hiromune [1 ]
Komura, Naoko [1 ]
机构
[1] Gifu Univ, Inst Glyco Core Res iGCORE, 1-1 Yanagido, Gifu 5011193, Japan
基金
日本科学技术振兴机构; 日本学术振兴会;
关键词
Glycosphingolipids; Gangliosides; Chemical synthesis; Chemo-enzymatic synthesis; DIVERSITY-ORIENTED STRATEGY; CHEMOENZYMATIC SYNTHESIS; GLYCOSYLATION; GANGLIOSIDES; DONORS; ESTER;
D O I
10.1016/j.cbpa.2023.102423
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
To accelerate the biological study and application of the diverse functions of glycosphingolipids (GSLs), the production of structurally defined GSLs has been greatly demanded. In this review, we focus on the recent developments in the chemical and chemoenzymatic synthesis of GSLs. In the chemical synthesis section, the syntheses based on glucosyl ceramide cassette, late -stage sialylation, and diversityoriented strategies for GSLs or ganglioside synthesis are highlighted, which delivered terpioside B, fluorescent sialyl lactotetraosyl ceramide, and analogs of lacto-ganglio-series GSLs, respectively. In the chemoenzymatic synthesis section, the synthesis of ganglioside GM1 by multistep one -pot multienzyme method and the total synthesis of highly complex ganglioside LLG-5 using a water-soluble lactosyl ceramide as a key substrate for enzymatic sialylation are described.
引用
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页数:8
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共 46 条
  • [1] p-tert-Butyl Groups Improve the Utility of Aromatic Protecting Groups in Carbohydrate Synthesis
    Asano, Sachi
    Tanaka, Hide-Nori
    Imamura, Akihiro
    Ishida, Hideharu
    Ando, Hiromune
    [J]. ORGANIC LETTERS, 2019, 21 (11) : 4197 - 4200
  • [2] The Manifold Roles of Sphingolipids in Viral Infections
    Avota, Elita
    Bodem, Jochen
    Chithelen, Janice
    Mandasari, Putri
    Beyersdorf, Niklas
    Schneider-Schaulies, Juergen
    [J]. FRONTIERS IN PHYSIOLOGY, 2021, 12
  • [3] Crossroads between bacterial and mammalian glycosyltransferases
    Brockhausen, Inka
    [J]. FRONTIERS IN IMMUNOLOGY, 2014, 5 : 1 - 21
  • [4] Chemoenzymatic Synthesis of Globo-series Glycosphingolipids and Evaluation of Their Immunosuppressive Activities
    Chiang, Pei-Yun
    Adak, Avijit K.
    Liang, Wei-Lun
    Tsai, Chen-Yen
    Tseng, Hsin-Kai
    Cheng, Jing-Yan
    Hwu, Jih Ru
    Yu, Alice L.
    Hung, Jung-Tung
    Lin, Chun-Cheng
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (16)
  • [5] A concise chemoenzymatic total synthesis of neutral Globo-series glycosphingolipids Globo A and Globo B, and Forssman and para-Forssman antigens
    Chiang, Yu-Ching
    Wu, Chun-Yen
    Chiang, Pei-Yun
    Adak, Avijit K.
    Lin, Chun-Cheng
    [J]. GLYCOCONJUGATE JOURNAL, 2023, 40 (05) : 551 - 563
  • [6] Chemoenzymatic Total Synthesis of the Neuritogenic Echinoderm Ganglioside LLG-5 and Related Analogues
    Cho, Yuan-Ting
    Adak, Avijit K.
    Su, Yung-Yu
    Chang, Ting-Wei
    Lin, Chun-Cheng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (20) : 3573 - 3588
  • [7] Terpioside B, a difucosyl GSL from the marine sponge Terpios sp is a potent inhibitor of NO release
    Costantino, Valeria
    Fattorusso, Ernesto
    Mangoni, Alfonso
    Teta, Roberta
    Panza, Elisabetta
    Ianaro, Angela
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (14) : 5310 - 5315
  • [8] Botulinum and Tetanus Neurotoxins
    Dong, Min
    Masuyer, Geoffrey
    Stenmark, Pal
    [J]. ANNUAL REVIEW OF BIOCHEMISTRY, VOL 88, 2019, 88 : 811 - 837
  • [9] The Total Synthesis of Starfish Ganglioside GP3 Bearing a Unique Sialyl Glycan Architecture
    Goto, Kenta
    Sawa, Maki
    Tamai, Hideki
    Imamura, Akihiro
    Ando, Hiromune
    Ishida, Hideharu
    Kiso, Makoto
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (24) : 8323 - 8331
  • [10] Stereocontrolled and convergent entry to CF2-sialosides:: Synthesis of CF2-linked ganglioside GM4
    Hirai, Go
    Watanabe, Toru
    Yamaguchi, Kazunori
    Miyagi, Taeko
    Sodeoka, Mikiko
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (50) : 15420 - +