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Journal of Carbohydrate Chemistry Volume 15, 1996 - Issue 5
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Original Articles

Synthetic Studies on Sialoglycoconjugates 88: Synthesis of Ganglioside GM3 and GM4 Analogs Containing 2- OR 3-Branched Fatty-Alkyl Residues in Place of Ceramide

Akira Hasegawa Department of Applied Bioorganic Chemistry, Gifu University, Gifu, 501-11, Japan
,
Naomi Suzuki Department of Applied Bioorganic Chemistry, Gifu University, Gifu, 501-11, Japan
,
Hideharu Ishida Department of Applied Bioorganic Chemistry, Gifu University, Gifu, 501-11, Japan
&
Makoto Kiso Department of Applied Bioorganic Chemistry, Gifu University, Gifu, 501-11, Japan
Pages 623-637 | Received 27 Jan 1996, Accepted 21 Mar 1996, Published online: 22 Aug 2006

Citations (25)

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Read on this site (9)

Michio Kurosu & Isao Kitagawa. (2006) Ganglioside GM3 Derivatives with Truncated Ceramide Moiety: Facial Synthesis and Inhibitory Activity against KB Cell Growth. Journal of Carbohydrate Chemistry 25:5, pages 427-439.
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Kyoko Fukunaga, Tsuyoshi Toyoda, Hideharu Ishida & Makoto Kiso. (2003) Synthesis of Lacto‐ and Neolacto‐series Ganglioside Analogs Containing N‐Glycolylneuraminic Acid: Probes for Investigation of Specific Receptor Structures Recognized by Influenza A Viruses . Journal of Carbohydrate Chemistry 22:9, pages 919-937.
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Nobumasa Otsubo, Hideharu Ishida & Makoto Kiso. (2002) AN EFFICIENT AND STRAIGHTFORWARD SYNTHESIS OF SIALYL Le X GLYCOLIPID AS A POTENT SELECTIN BLOCKER[[1]]. Journal of Carbohydrate Chemistry 21:3, pages 247-255.
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Takayuki Ando, Hideharu Ishida*Makoto Kiso*. (2001) A HIGHLY EFFICIENT SYNTHETIC ROUTE TO α(2→3)/α(2→6) DISIALYL LEWIS A AS A CANCER ASSOCIATED CARBOHYDRATE ANTIGEN1 . Journal of Carbohydrate Chemistry 20:5, pages 425-430.
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Nobumasa Otsubo, Masanori Yamaguchi, Hideharu Ishida & Makoto Kiso. (2001) THE FIRST, EFFICIENT SYNTHESIS OF NOVEL SLex NEOGLYCOLIPIDS CONTAINING N-DEACETYLATED AND LACTAMIZED SIALIC ACID: KEY LIGAND STRUCTURES FOR SELECTIN BINDING[1] . Journal of Carbohydrate Chemistry 20:3-4, pages 329-334.
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Xiaodong Zhang, Tomohide Kamiya, Nobumasa Otsubo, Hideharu Ishida & Makoto Kiso. (1999) Chemoenzymatic Synthesis of Ganglioside Gm4 Analogs as Potential Immunosuppressive Agents. Journal of Carbohydrate Chemistry 18:2, pages 225-239.
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Takao Ikami, Noboru Tomiya, Takashi Morimoto, Noriyuki Iwata, Reiko Yamashita, Takahito Jomori, Toshinao Usui, Yasuo Suzuki, Harunari Tanaka, Daisei Miyamoto, Hideharu Ishida, Akira Hasegawa & Makoto Kiso. (1998) Synthetic Studies on Selectin Ligands/Inhibitors: Synthesis and Biological Activity of the Sulfated and Phosphorylated Multivalent β-D-Galactopyranosides Containing Fatty Alkyl Residues . Journal of Carbohydrate Chemistry 17:4-5, pages 499-518.
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Takao Ikami, Hitoshi Hamajima, Toshinao Usui, Takahiko Mitani, Hideharu Ishida, Makoto Kiso & Akira Hasegawa. (1997) Synthetic Studies on Selectin Ligands/Inhibitors: One-Pot Synthesis of the Mono- and Oligo-Sulfated 2-(Tetradecyl)Hexadecyl β-D-Galacto- and Lactopyranosides as the Sulfatide Mimetics . Journal of Carbohydrate Chemistry 16:6, pages 859-875.
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Eiji Tanahashi, Katsutoshi Murase, Mika Shibuya, Yumie Igarashi, Hideharu Ishida, Akira Hasegawa & Makoto Kiso. (1997) Synthetic Studies on Selectin Ligands/Inhibitors: A Systematic Synthesis of Sulfatide and Its Higher Congeners Carrying 2-(Tetradecyl)Hexadecyl Group as a Ceramide Substitute . Journal of Carbohydrate Chemistry 16:6, pages 831-858.
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Articles from other publishers (16)

Rita Pal, Ayano Yamazaki, Naoko Komura, Hide-Nori Tanaka, Akihiro Imamura, Hideharu Ishida & Hiromune Ando. (2024) Convergent synthesis of functionalized derivatives of stage-specific embryonic antigens 3 & 4. Carbohydrate Research 535, pages 108990.
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Fumi Yoshida, Hiroki Yoshinaka, Hidenori Tanaka, Shinya Hanashima, Yoshiki Yamaguchi, Mikio Ishihara, Miyuki Saburomaru, Yuki Kato, Risa Saito, Hiromune Ando, Makoto Kiso, Akihiro Imamura & Hideharu Ishida. (2018) Synthesis of the Core Oligosaccharides of Lipooligosaccharides from Campylobacter jejuni : A Putative Cause of Guillain–Barré Syndrome . Chemistry – A European Journal 25:3, pages 796-805.
Crossref
T. Ando, A. Imamura, H. Ishida & M. Kiso. 2013. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering.
N. Ogasawara, Y. U. Katagiri, N. Kiyokawa, T. Kaneko, B. Sato, H. Nakajima, Y. Miyagawa, Y. Kushi, H. Ishida, M. Kiso, H. Okita, T. Sato & J. Fujimoto. (2010) Accelerated biosynthesis of neolacto-series glycosphingolipids in differentiated mouse embryonal carcinoma F9 cells detected by using dodecyl N-acetylglucosaminide as a saccharide primer. Journal of Biochemistry 149:3, pages 321-330.
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Akihiro Imamura, Hiromune Ando, Hideharu Ishida & Makoto Kiso. (2009) Ganglioside GQ1b: Efficient Total Synthesis and the Expansion to Synthetic Derivatives To Elucidate Its Biological Roles. The Journal of Organic Chemistry 74:8, pages 3009-3023.
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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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Masahiro Wakao & Yasuo Suda. 2008. Glycoscience. Glycoscience 1629 1669 .
Noriyasu Hada, Taishi Nakashima, Suraj Prakash Shrestha, Ryo Masui, Yuji Narukawa, Kayoko Tani & Tadahiro Takeda. (2007) Synthesis and biological activities of glycosphingolipid analogues from marine sponge Aplysinella rhax. Bioorganic & Medicinal Chemistry Letters 17:21, pages 5912-5915.
Crossref
T. Ando, A. Imamura, H. Ishida & M. Kiso. 2007. Comprehensive Glycoscience. Comprehensive Glycoscience 797 813 .
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.
Crossref
Takayuki Ando, Hideharu Ishida & Makoto Kiso. (2003) First total synthesis of α-(2→3)/α-(2→6)-disialyl lactotetraosyl ceramide and disialyl Lewis A ganglioside as cancer-associated carbohydrate antigens. Carbohydrate Research 338:6, pages 503-514.
Crossref
Christian Gege & Richard R Schmidt. (2002) Synthesis of dimeric lactose and dimeric (sialyl) LewisX glycolipids. Carbohydrate Research 337:12, pages 1089-1094.
Crossref
Nobumasa Otsubo, Hideharu Ishida*Makoto Kiso*. (2001) Synthesis of novel ganglioside GM4 analogues containing N-deacetylated and lactamized sialic acid: probes for searching new ligand structures for human L-selectin. Carbohydrate Research 330:1, pages 1-5.
Crossref
Beat Ernst, Gerald W. Hart & Pierre SinaýRichard R. Schmidt & Karl‐Heinz Jung. 2000. Carbohydrates in Chemistry and Biology. Carbohydrates in Chemistry and Biology 5 59 .
Nobumasa Otsubo, Hideharu Ishida & Makoto Kiso. (2000) The first, highly efficient synthesis of spacer-armed O-glycans on GlyCAM-1 and PSGL-1: the counter-receptors for L- and P-selectin. Tetrahedron Letters 41:20, pages 3879-3882.
Crossref
Takao Ikami, Hideharu Ishida & Makoto Kiso. 2000. Sphingolipid Metabolism and Cell Signaling Part A. Sphingolipid Metabolism and Cell Signaling Part A 547 568 .

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