Synthesis of Two Lewis^X Trisaccharides Using Regiospecific Glycosylation Reactions

References

• Lasky , L. A. 1992 . Selectin interpretors of cell‐specific carbohydrate information during inflammation . Science , 258 : 964 – 969 .
   PubMed Web of Science ®Google Scholar
• McEver , R. P. 1992 . Leucocyte endothelial cell interactions. Curr . Opin. Cell Biol. , 4 : 840 – 849 .
   PubMedGoogle Scholar
• Stoolman , L. M. 1992 . Cell Surface Carbohydrates and Cell Development Edited by: Fukuda , M. 71 – 97 . Boca Raton : CRC Press .
   Google Scholar
• Kishimoto , T. K. 1993 . Structure Function and Regulation of Molecules Involved in Leukocyte Adhesion Edited by: Lipsky , P. E. , Rothlein , R. , Kishimoto , T. K. , Fanes , R. B. and Smith , C. W. 107 – 134 . New York : Spinger‐Verlag .
   Google Scholar
• Lowe , J. B. , Stoolman , L. M. , Nair , R. P. , Larsen , R. D. , Berhend , T. L. and Marks , R. M. 1990 . Elam‐1‐dependent cell adhesion to vascular endothelium determined by a transfected human fucosyltransferase cDNA . Cell , 63 : 475 – 484 .
   PubMed Web of Science ®Google Scholar
• Yuen , C.‐T. , Lawson , A. M. , Chai , W. , Larkin , M. , Stoll , M. S. , Stuart , A. C. , Sullivan , E. X. , Ahern , T. J. and Feizi , T. 1992 . Novel sulfated ligands for the cell adhesion molecule E‐selectin revealed by the neoglycolipid technology among O‐linked oligosaccharides on an ovarian cystadenoma glycoprotein . Biochemistry , 31 : 9126 – 9131 .
   PubMed Web of Science ®Google Scholar
• Komba , S. , Yamaguchi , M. , Ishida , H. and Kiso , M. 2001 . 6‐O‐sulfo de‐N‐acetylsialyl Lewis X as a novel high‐affinity ligand for human L‐selectin: Total synthesis and structural characterization . Biol. Chem. , 382 : 233 – 240 .
   Google Scholar
• Imai , Y. , Lasky , L. A. and Rosen , S. D. 1993 . Sulphation requirement for Gly‐CAM‐I, an endothelial ligand for L‐selectin . Nature , 361 : 555 – 557 .
   PubMed Web of Science ®Google Scholar
• Danishefsky , S. J. , Gervay , J. , Peterson , J. M. , McDonald , F. E. , Koseki , K. , Oriyama , T. , Griffith , D. A. , Wong , C. H. and Dumos , D. P. 1992 . Azaglycosylation of complex stannyl alkoxides with glycal‐derived iodosulfonamides: A straightforward synthesis of sialyl‐Lewis X antigen and other oligosaccharide domains . J. Am. Chem. Soc. , 114 : 8329 – 8331 .
   Web of Science ®Google Scholar
• Hasegawa , A. , Fushimi , K. , Ishida , H. and Kiso , M. 1993 . Sialoglycoconjugates. 52: Synthesis of sialyl Lewis‐X analogs containing azidoalkyl groups at the reducing end . J. Carbohydr. Chem. , 12 : 1203 – 1216 .
   Web of Science ®Google Scholar
• Hasegawa , A. , Ito , K. , Ishida , H. and Kiso , M. 1995 . Synthetic studies on sialoglycoconjugates. 70: Synthesis of sialyl and sulfo‐Lewis‐X analogs containing a ceramide or 2‐(tetradecyl) hexadecyl residue . J. Carbohydr. Chem. , 14 : 353 – 368 .
   Web of Science ®Google Scholar
• Manzoni , L. , Lay , L. and Schmidt , R. R. 1998 . Synthesis of Lewis A and Lewis X pentasaccharides based on N‐trichloroethoxycarbonyl protection . J. Carbohydr. Chem. , 17 : 739 – 758 .
   Web of Science ®Google Scholar
• Danishefsky , S. J. , Gervay , J. , Peterson , J. M. , McDonald , F. E. , Koseki , K. , Griffith , D. A. , Oriyama , T. and Marsden , S. P. 1995 . Application of glycals to the synthesis of oligosaccharides: Convergent total syntheses of the Lewis X trisaccharide sialyl Lewis X antigenic determinant and higher congeners . J. Am. Chem. Soc. , 117 : 1940 – 1953 .
   Web of Science ®Google Scholar
• Nicolau , K. C. , Hummel , C. W. and Iwabuchi , Y. 1992 . Total synthesis of sialyl dimeric Lex . J. Am. Chem. Soc. , 114 : 3126 – 3128 .
   Google Scholar
• Nifant'ev , N. E. , Tsvetkov , Y. E. , Shashkov , A. S. , Kononov , L. O. , Menshov , V. M. , Tuzikov , A. B. and Bovin , N. V.J. 1996 . Selectin receptors 4: Synthesis of tetrasaccharides sialyl Lewis A and sialyl Lewis X containing a spacer group . J. Carbohydr. Chem. , 15 : 939 – 953 .
   Web of Science ®Google Scholar
• Kameyama , A. , Ishida , H. and Kiso , M. 1991 . Total synthesis of sialyl Lewis X. Carbohydr. Res. , 209 : C1 – C4 .
   Web of Science ®Google Scholar
• Kameyama , A. , Ehara , T. , Yamada , Y. , Ishida , H. , Kiso , M. and Hasegawa , A. 1995 . A total synthesis of dimeric LeX ganglioside . J. Carbohydr. Chem. , 14 : 507 – 523 .
   Web of Science ®Google Scholar
• Ellervik , U. and Magnusson , G. 1998 . Regio‐ and stereo‐differentiated glycosylation . J. Org. Chem. , 63 : 9314 – 9322 .
   Web of Science ®Google Scholar
• Henry , B. , Desvaux , H. , Pristchepa , M. , Berthault , P. , Zhang , Y. , Mallet , J.‐M. , Esnault , J. and Sinay , P. 1999 . NMR study of a Lewis X pentasaccharide derivative solution structure and interaction with cations . Carbohydr. Res. , 315 : 48 – 62 .
   PubMed Web of Science ®Google Scholar
• Misra , A. K. , Ding , Y. , Lowe , J. B. and Hindsgaul , O. 2000 . A concise synthesis of the 6‐O‐ and 6‐O‐sulfated analogues of the sialyl Lewis X tetrasaccharide . Bioorg. Med. Chem. , 10 : 1505 – 1509 .
   Google Scholar
• Tsukida , T. , Yoshida , M. , Kurokawa , K. , Nakai , Y. , Achiha , T. , Kiyoi , T. and Kondo , H. 1997 . A highly practical synthesis of sulfated Lewis X: One‐pot two‐step glycosylation using “armed/disarmed” coupling and selective benzoylation and sulfation . J. Org. Chem. , 62 : 6876 – 6881 .
   Google Scholar
• Kiyoi , T. , Inone , Y. , Ohmoto , H. , Yoshida , M. , Kiso , M. and Kondo , H. 1998 . Synthesis of sialyl Lewis X pentasaccharide analogue for high‐throughput screening of selectin blockers . Bioorg. Med. Chem. , 6 : 587 – 593 .
   Google Scholar
• Kameyama , A. , Ishida , H. , Kiso , M. and Hasegawa , A. 1994 . Synthetic studies on sialoglycoconjugates. Total synthesis of tumor‐associated ganglioside, sialyl Le(A) . J. Carbohydr. Chem. , 13 : 641 – 654 .
   Web of Science ®Google Scholar
• Numomura , S. , Iida , M. , Numata , M. , Sugimoto , M. and Ogawa , T. 1994 . Total synthesis of sulfated Le pentaosyl ceramide . Carbohydr. Res. , 263 : C1 – C6 .
   Google Scholar
• Ellervik , U. and Magnusson , G. 1996 . Glycosylation with N‐troe‐protected glycosyl donors . Carbohydr. Res. , 280 : 251 – 260 .
   PubMedGoogle Scholar
• Lonn , H. 1985 . Synthesis of a tri‐ and a hepta‐saccharide which contain fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins . Carbohydr. Res. , 139 : 105 – 113 .
   PubMed Web of Science ®Google Scholar
• Komba , S. , Ishida , H. , Kiso , M. and Hasegawa , A. 1996 . Synthesis and biological activities of three sulfated sialyl Lex ganglioside analogues for clarifying the real carbohydrate ligand structure of L‐selectin . Bioorg. Med. Chem. , 4 : 1833 – 1848 .
   PubMed Web of Science ®Google Scholar
• Yde , M. and De Bruyne , C. K. 1973 . Synthesis of para‐substituted phenyl 1‐thiogalactopyranosides . Carbohydr. Res. , 26 : 227 – 229 .
   Google Scholar