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Original Articles

Synthetic Studies on Sialoglycoconjugates 22: Total Synthesis of Tumor-Associated Ganglioside, Sialyl Lewis X1

Pages 549-560 | Published online: 27 Feb 2008

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Read on this site (17)

Toshihiko Sawada, Tomohiro Hashimoto, Hirofumi Nakano, Mikiji Shigematsu, Hideharu Ishida & Makoto Kiso. (2006) Conformational Study of α‐N‐Acetyl‐D‐Neuraminic Acid by Density Functional Theory. Journal of Carbohydrate Chemistry 25:5, pages 387-405.
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Hiroyasu Furui , Keiko Ando-Furui, Haruko Inagaki, Takayuki Ando, Hideharu Ishida & Makoto Kiso. (2001) SYNTHESIS OF SIALYL- AND SULFO-Lex/Lea ANALOGS CONTAINING N-ALKYL-1-DEOXYNOJIRIMYCIN AS POTENTIAL SELECTIN BLOCKERS[1] . Journal of Carbohydrate Chemistry 20:9, pages 789-812.
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U.S. Chowdhury. (2000) Synthesis of the Key Disaccharide of 3′-Sulfo Lewis X and Lewis A: The Novel E-Selectin Ligand. Synthetic Communications 30:20, pages 3785-3792.
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Keun-Hong Park, Mitsuaki Goto, Ryotaro Takei, Atsushi Maruyama, Kazukiyo Kobayashi, Jun-Ichi Miyazaki, Chong-Su Cho & Toshihiro Akaike. (2000) Enhanced effect of sulfonylurea (SU) in copolymer comprising a sugar moiety and SU derivative as double ligands on insulin secretion from MIN6 cells . Journal of Biomaterials Science, Polymer Edition 11:9, pages 903-913.
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Keisuke Adachi, Yutaka Yamada, Hiroaki Wada, Akihiko Kameyama, Hideharu Ishida & Makoto Kiso. (1998) Synthesis of Sialyl Lewis X Ganglioside Analogs Containing A Variable Length Spacer Between the Sugar and Lipophilic Moieties . Journal of Carbohydrate Chemistry 17:4-5, pages 595-607.
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Tomohiro Terada, Hirofumi Simada, Hideharu Ishida, Makoto Kiso & Akira Hasegawa. (1998) Synthetic Studies on Sialoglycoconjugates 104: Synthesis of Kdn-Lewis X Ganglioside Analogs Containing Modified Reducing Terminal and L-Rhamnose in Place of L-Fucose . Journal of Carbohydrate Chemistry 17:4-5, pages 519-534.
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Gyula Dekany, Karen Wright & Istvan Toth. (1997) An Economical Synthesis of Lewis X, Sialyl Lewis X and Their α-Galactosyl Analogues. Journal of Carbohydrate Chemistry 16:7, pages 983-999.
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Eva Eichler, HaroldJ. Jennings & DennisM. Whitfield. (1997) Synthesis of a Single Repeat Unit of Type VIII Group B Streptococcus Capsular Polysaccharide . Journal of Carbohydrate Chemistry 16:4-5, pages 385-411.
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Yataka Makimura, Hideharu Ishida, Makoto Kiso & Akira Hasegawa. (1996) Synthetic Studies on Tumor-Associated Antigens: Efficient Syntheses of Lea and Sialyl-Lea Oligosaccharides, and Their Deaminated Analogs1 . Journal of Carbohydrate Chemistry 15:9, pages 1097-1118.
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NikolayE. Nifant'ev, YuryE. Tsvetkov, AlexanderS. Shashkov, LeonidO. Kononov, VladimirM. Menshov, AlexanderB. Tuzikov & NicolaiV. Bovin. (1996) Selectin Receptors 4: Synthesis of Tetrasaccharides Sialyl Lewis A and Sialyl Lewis X Containing A Spacer Group1,2 . Journal of Carbohydrate Chemistry 15:8, pages 939-953.
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Gyula Dekany, Karen Wright, Peter Ward & Istvan Toth. (1996) Synthesis of Sialyl Lewis X Analogues. Journal of Carbohydrate Chemistry 15:4, pages 383-398.
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Akihiko Kameyama, Taro Ehara, Yutaka Yamada, Hideharu Ishida, Makoto Kiso & Akira Hasegawa. (1995) A Total Synthesis of Sialyl Dimeric Lex Ganglioside1 . Journal of Carbohydrate Chemistry 14:4-5, pages 507-523.
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Gyula Dekany, Peter Ward & Istvan Toth. (1995) Synthesis of Fully and Partially Protected Alkyl 1-Thio-β-l-fucopyranosides. Journal of Carbohydrate Chemistry 14:2, pages 227-236.
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Akihiko Kameyama, Hideharu Ishida, Makoto Kiso & Akira Hasegawa. (1994) Synthetic Studies on Sialoglycoconjugates 59: Total Synthesis of Tumor-Associated Ganglioside, Sialyl Le. Journal of Carbohydrate Chemistry 13:5, pages 641-654.
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Akihiro Imamura, Hiromune Ando & Hideharu Ishida. 2023. Glycolipids. Glycolipids 89 100 .
Riping Phang & Chun-Hung Lin. (2022) Synthesis of Type-I and Type-II LacNAc-Repeating Oligosaccharides as the Backbones of Tumor-Associated Lewis Antigens. Frontiers in Immunology 13.
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Monalisa Kundu, Arin Gucchait & Anup Kumar Misra. (2020) Convergent synthesis of a pentasaccharide corresponding to the cell wall O-polysaccharide of enteropathogenic Escherichia coli O115. Tetrahedron 76:8, pages 130952.
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Kenta Goto, Hideki Tamai, Yoh Takeda, Hide-Nori Tanaka, Takashi Mizuno, Akihiro Imamura, Hideharu Ishida, Makoto Kiso & Hiromune Ando. (2019) Total Synthesis of Sialyl Inositol Phosphosphingolipids CJP-2, CJP-3, and CJP-4 Isolated from Feather Star Comanthus japonica . Organic Letters 21:11, pages 4054-4057.
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Abhishek Santra, Hai Yu & Xi Chen. 2019. Synthetic Glycomes. Synthetic Glycomes 226 253 .
Akihiro Imamura & Makoto Kiso. 2018. Gangliosides. Gangliosides 293 310 .
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T. Kasai, D. Nakane, H. Ishida, H. Ando, M. Kiso & M. Miyata. (2012) Role of Binding in Mycoplasma mobile and Mycoplasma pneumoniae Gliding Analyzed through Inhibition by Synthesized Sialylated Compounds. Journal of Bacteriology 195:3, pages 429-435.
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Therese Buskas, Pamela Thompson & Geert‐Jan Boons. 2009. Carbohydrate‐Based Vaccines and Immunotherapies. Carbohydrate‐Based Vaccines and Immunotherapies 263 311 .
Yasuhito Nagai, Naoyuki Ito, Israt Sultana & Takeshi Sugai. (2008) Regio- and chemoselective manipulation under mild conditions on glucosamine derivatives for oligosaccharide synthesis and its application toward N-acetyl-d-lactosamine and Lewis X trisaccharide. Tetrahedron 64:40, pages 9599-9606.
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Christian Gege, Gabriele Schumacher, Ulrich Rothe, Richard R. Schmidt & Gerd Bendas. (2008) Visualization of sialyl LewisX glycosphingolipid microdomains in model membranes as selectin recognition motifs using a fluorescence label. Carbohydrate Research 343:14, pages 2361-2368.
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Masanori Yamaguchi, Hideharu Ishida & Makoto Kiso. (2008) Total synthesis of 6-O-sulfo-sialylparagloboside: a widely useful glycoprobe for biochemical research. Carbohydrate Research 343:10-11, pages 1849-1857.
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María Asunción Campanero-Rhodes, Robert A. Childs, Makato Kiso, Shiro Komba, Christine Le Narvor, Joanna Warren, Diana Otto, Paul R. Crocker & Ten Feizi. (2006) Carbohydrate microarrays reveal sulphation as a modulator of siglec binding. Biochemical and Biophysical Research Communications 344:4, pages 1141-1146.
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Nobumasa Otsubo, Hideharu Ishida, Reiji Kannagi & Makoto Kiso. (2005) Design and synthesis of a novel neo-glycolipid containing sialyl Lewis X determinant carried on the mucin GlcNAcβ1-6GalNAcα core structure. Tetrahedron: Asymmetry 16:7, pages 1321-1327.
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Masanori Yamaguchi, Hideharu Ishida, Akiko Kanamori, Reiji Kannagi & Makoto Kiso. (2003) Studies on the endogenous L-selectin ligands: systematic and highly efficient total synthetic routes to lactamized-sialyl 6-O-sulfo Lewis X and other novel gangliosides containing lactamized neuraminic acid. Carbohydrate Research 338:24, pages 2793-2812.
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Hiromune Ando, Hideharu Ishida & Makoto Kiso. 2003. Carbohydrates. Carbohydrates 277 310 .
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Isao Ohtsuka, Noriyasu Hada, Hiroko Ohtaka, Mutsumi Sugita & Tadahiro Takeda. (2002) Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Amphoteric Glycolipid Analogues from the Porcine Nematode, Ascaris suum.. Chemical and Pharmaceutical Bulletin 50:5, pages 600-604.
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Kerry Routenberg Love, Rodrigo B. Andrade & Peter H. Seeberger. (2001) Linear Synthesis of a Protected H-Type II Pentasaccharide Using Glycosyl Phosphate Building Blocks. The Journal of Organic Chemistry 66:24, pages 8165-8176.
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Shiro Komba, Masanori Yamaguchi, Hideharu Ishida & Makoto Kiso. (2001) 6-O-Sulfo De-N-Acetylsialyl Lewis X as a Novel High-Affinity Ligand for Human L-Selectin: Total Synthesis and Structural Characterization. Biological Chemistry 382:2.
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Christian Gege, Stefan Oscarson & Richard R Schmidt. (2001) Synthesis of fluorescence labeled sialyl LewisX glycosphingolipids. Tetrahedron Letters 42:3, pages 377-380.
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Ten Feizi. 2001. Mammalian Carbohydrate Recognition Systems. Mammalian Carbohydrate Recognition Systems 201 223 .
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Beat Ernst, Gerald W. Hart & Pierre SinaýHideharu Ishida. 2000. Carbohydrates in Chemistry and Biology. Carbohydrates in Chemistry and Biology 305 317 .
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Shiro Komba, Christine Galustian, Hideharu Ishida, Ten Feizi, Reiji Kannagi & Makoto Kiso. (1999) Die erste Totalsynthese des 6-Sulfo-de-N-acetylsialyl-Lewisx-Gangliosids: ein hervorragender Ligand für menschliches L-Selectin. Angewandte Chemie 111:8, pages 1203-1206.
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Noriyasu Hada, Eriko Hayashi & Tadahiro Takeda. (1999) Synthetic studies on glycosphingolipids from the parasite Echinococcus multilocularis. Carbohydrate Research 316:1-4, pages 58-70.
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Gerhard Kretzschmar & Wilhelm Stahl. (1998) Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine. Tetrahedron 54:23, pages 6341-6358.
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Nobumasa Otsubo, Hideharu Ishida, Makoto Kiso & Akira Hasegawa. (1998) Synthesis of sialyl Lex ganglioside analogues modified at C-6 of the galactose residue to elucidate the mechanism of selection recognition. Carbohydrate Research 306:4, pages 517-530.
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William J. Sanders, David D. Manning, Kathryn M. Koeller & Laura L. Kiessling. (1997) Synthesis of sulfated trisaccharide ligands for the selectins. Tetrahedron 53:48, pages 16391-16422.
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Christine Galustian, Alexander M. Lawson, Shiro Komba, Hideharu Ishida, Makoto Kiso & Ten Feizi. (1997) Sialyl-LewisxSequence 6-O-Sulfated atN-Acetylglucosamine Rather Than at Galactose Is the Preferred Ligand forl-Selectin and De-N-acetylation of the Sialic Acid Enhances the Binding Strength. Biochemical and Biophysical Research Communications 240:3, pages 748-751.
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