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Journal of Carbohydrate Chemistry Volume 12, 1993 - Issue 8
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Original Articles

Synthetic Studies on Sialoglycoconjugates 52: Synthesis of Sialyl Lewis X Analogs Containing Azidoalkyl Groups at the Reducing End

Akira Hasegawa Department of Applied Bioorganic Chemistry, Gifu University, Gifu, 501-11, Japan
,
Koshiro Fushimi 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 1203-1216 | Received 10 Apr 1993, Published online: 24 Sep 2006

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Debaraj Mukherjee, Sujit Kumar Sarkar, Partha Chattopadhyay & Uday Shankar Chowdhury. (2005) Synthesis of Two LewisX Trisaccharides Using Regiospecific Glycosylation Reactions. Journal of Carbohydrate Chemistry 24:3, pages 251-259.
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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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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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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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Akira Hasegawa, Kenichi Ito, Hideharu Ishida & Makoto Kiso. (1995) Synthetic Studies on Sialoglycoconjugates 70: Synthesis of Sialyl and Sulfo Lewis × Analogs Containing a Ceramide or 2-(Tetradecyl)hexadecyl Residue. Journal of Carbohydrate Chemistry 14:3, pages 353-368.
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Articles from other publishers (34)

Qiushi Chen, Han Liu & Xuechen Li. (2023) Essential functions, syntheses and detection of sialyl Lewis X on glycoproteins. Exploration of Drug Science, pages 31-54.
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Marco Brito-AriasMarco Brito-Arias. 2022. Synthesis and Characterization of Glycosides. Synthesis and Characterization of Glycosides 101 228 .
Marco Brito-AriasMarco Brito-Arias. 2016. Synthesis and Characterization of Glycosides. Synthesis and Characterization of Glycosides 81 168 .
Leonid O. Kononov, Nelly N. Malysheva & Anna V. Orlova. (2009) Stereoselectivity of Glycosylation May Change During the Reaction Course: Highly α‐Stereoselective Sialylation Achieved by Supramer Approach. European Journal of Organic Chemistry 2009:5, pages 611-616.
Crossref
Ari Asnani & France-Isabelle Auzanneau. (2008) Synthesis of Lewis X and three Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively. Carbohydrate Research 343:10-11, pages 1653-1664.
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. 2007. Synthesis and Characterization of Glycosides. Synthesis and Characterization of Glycosides 68 137 .
Balaram Mukhopadhyay & Robert A Field. (2004) Synthesis of l-arabinose-containing fragments of the oat root saponin Avenacin A-1. Carbohydrate Research 339:7, pages 1285-1291.
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Ari Asnani & France-Isabelle Auzanneau. (2003) Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively. Carbohydrate Research 338:10, pages 1045-1054.
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Anna Rencurosi, Laura Poletti, Giovanni Russo & Luigi Lay. (2003) Lipase‐Catalysed Regioselective Acylations in Combination with Regioselective Glycosylations as a Strategy for the Synthesis of Oligosaccharides: Synthesis of a Series of Fucosyllactose Building Blocks. European Journal of Organic Chemistry 2003:9, pages 1672-1680.
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Hiromune Ando, Hideharu Ishida & Makoto Kiso. 2003. Carbohydrates. Carbohydrates 277 310 .
Jie Xia, James L. Alderfer, Conrad. F. Piskorz & Khushi L. Matta. (2001) The 2-Naphthylmethyl (NAP) Group in Carbohydrate Synthesis: First Total Synthesis of the GlyCAM-1 Oligosaccharide Structures. Chemistry 7:2, pages 356-367.
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Frank M. Unger. 2001. 207 435 .
Beat Ernst, Gerald W. Hart & Pierre SinaýMakoto Kiso, Hideharu Ishida & Hiromi Ito. 2000. Carbohydrates in Chemistry and Biology. Carbohydrates in Chemistry and Biology 345 365 .
Horst Kunz, Birgit Löhr & Jörg Habermann. 1999. Carbohydrates. Carbohydrates 187 227 .
Hartmuth C. Kolb & Beat Ernst. (2006) Development of Tools for the Design of Selectin Antagonists. Chemistry – A European Journal 3:10, pages 1571-1578.
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Luigi Lay, Rainer Windmüller, Stefan Reinhardt & Richard R. Schmidt. (1997) A simple access to lactose-derived building blocks required in glycoconjugate synthesis. Carbohydrate Research 303:1, pages 39-49.
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Roland Schauer & Johannis P. Kamerling. 1997. Glycoproteins II. Glycoproteins II 243 402 .
Per J. Garegg. 1997. Advances in Carbohydrate Chemistry and Biochemistry Volume 52. Advances in Carbohydrate Chemistry and Biochemistry Volume 52 179 205 .
Inka Brockhausen & William KuhnsInka Brockhausen & William Kuhns. 1997. Glycoproteins and Human Disease. Glycoproteins and Human Disease 221 226 .
Shiro Komba, Hideharu Ishida, Makoto Kiso & Akira Hasegawa. (1996) Synthesis and biological activities of three sulfated sialyl Lex ganglioside analogues for clarifying the real carbohydrate ligand structure of L-selectin. Bioorganic & Medicinal Chemistry 4:11, pages 1833-1847.
Crossref
Jeremy C. Prodger, Mark J. Bamford, Michael I. Bird, Paul M. Gore, Duncan S. Holmes, Richard Priest & Victoria Saez. (1996) Mimics of the sialyl Lewis X tetrasaccharide. Replacement of the N-Acetylglucosamine sugar with simple C2-symmetric 1,2-diols. Bioorganic & Medicinal Chemistry 4:6, pages 793-801.
Crossref
Mark J. Bamford, Michael Bird, Paul M. Gore, Duncan S. Holmes, Richard Priest, Jeremy C. Prodger & Victoria Saez. (1996) Synthesis and biological activity of conformationally constrained sialyl Lewis X analogues with reduced carbohydrate character. Bioorganic & Medicinal Chemistry Letters 6:3, pages 239-244.
Crossref
Akira Hasegawa, Mitsutoshi Kato, Takashi Ando, Hideharu Ishida & Makoto Kiso. (1995) Synthesis of sialyl lewis X ganglioside analogues containing modified l-fucose residues. Carbohydrate Research 274, pages 165-181.
Crossref
Ulrich Sprengard, Gerhard Kretzschmar, Eckart Bartnik, Christoph Hüls & Horst Kunz. (2003) Synthesis of an RGD‐Sialyl‐Lewis X Glycoconjugate: A New Highly Active Ligand for P‐Selectin ** . Angewandte Chemie International Edition in English 34:9, pages 990-993.
Crossref
Ulrich Sprengard, Gerhard Kretzschmar, Eckart Bartnik, Christoph Hüls & Horst Kunz. (2006) Synthese eines RGD‐Sialyl‐Lewis x ‐Glycokonjugats: ein neuer, hochwirksamer Ligand für P‐Selektin . Angewandte Chemie 107:9, pages 1104-1107.
Crossref
Gerd Böhm & Herbert Waldmann. (1995) Synthesis of glycosides of fucose under neutral conditions in solutions of LiClO4 in organic solvents. Tetrahedron Letters 36:22, pages 3843-3846.
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Jeremy C. Prodger, Mark J. Bamford, Paul M. Gore, Duncan S. Holmes, Victoria Saez & Peter Ward. (1995) Synthesis of a novel analogue of sialyl Lewis X. Tetrahedron Letters 36:13, pages 2339-2342.
Crossref
Akira Hasegawa. (1995) Systematic Synthesis and Molecular analysis of the Biologically Functional Glycoconjugates, and Application as Indispensable Probes for the Life Sciences. Nippon Nōgeikagaku Kaishi 69:9, pages 1147-1154.
Crossref
Wilhelm Stahl, Ulrich Sprengard, Gerhard Kretzschmar & Horst Kunz. (2003) Synthesis of Deoxy Sialyl Lewis x Analogues, Potential Selectin Antagonists . Angewandte Chemie International Edition in English 33:20, pages 2096-2098.
Crossref
Wilhelm Stahl, Ulrich Sprengard, Gerhard Kretzschmar & Horst Kunz. (2006) Synthese von Desoxy‐Sialyl‐Lewis x ‐Analoga, potentiellen Selectin‐Antagonisten . Angewandte Chemie 106:20, pages 2186-2188.
Crossref
Akira Hasegawa, Takashio Ando, Mitsutoshi Kato, Hideharu Ishida & Makoto Kiso. (1994) Synthesis of deoxy-l-fucose-containing sialyl Lewis X ganglioside analogues. Carbohydrate Research 257:1, pages 67-80.
Crossref
Kamaljit Singh, Alfonso Fernández-Mayoralas & Manuel Martín-Lomas. (1994) Synthesis of oligosaccharides structurally related to E-selection ligands. J. Chem. Soc., Chem. Commun.:6, pages 775-776.
Crossref
Makoto Kiso & Akira Hasegawa. 1994. Neoglycoconjugates Part A: Synthesis. Neoglycoconjugates Part A: Synthesis 173 183 .
Akira Hasegawa & Makoto Kiso. 1994. Neoglycoconjugates Part A: Synthesis. Neoglycoconjugates Part A: Synthesis 158 173 .

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