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Original Articles

THE FIRST, EFFICIENT SYNTHESIS OF NOVEL SLex NEOGLYCOLIPIDS CONTAINING N-DEACETYLATED AND LACTAMIZED SIALIC ACID: KEY LIGAND STRUCTURES FOR SELECTIN BINDINGCitation[1]

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Pages 329-334 | Received 25 Dec 2000, Accepted 05 Feb 2001, Published online: 16 Aug 2006

REFERENCES AND NOTES

  • Sawada , N. , Ito , M. , Ishida , H. and Kiso , M. in press . The First Synthesis of Glycan Parts of Lactoganglio- and Neolactoganglio-Series Gangliosides . Tetrahedron Lett. , Synthetic Studies on Sialoglycoconjugates, Part 120. For Part 119, see
  • Simanek , E. E. , McGarver , G. J. , Jablonowski , J. A. and Wong , C.-H. 1998 . Selectin-carbohydrate Interactions: from Natural Ligands to Designed Mimics . Chem. Rev. , 98 : 833 – 862 .
  • Komba , S. , Galustian , C. , Ishida , H. , Feizi , T. , Kannagi , R. and Kiso , M. 1999 . The First Total Synthesis of 6-Sulfo-de-N-acetylsialyl Lewis x Ganglioside: A Superior Ligand for Human L-Selectin . Angew. Chem. Int. Ed. , 38 ( 8 ) : 1131 – 1133 .
  • Mitsuoka , C. , Ohmori , K. , Kimura , N. , Kanamori , A. , Komba , S. , Ishida , H. , Kiso , M. and Kannagi , R. 1999 . Regulation of Selectin Binding Activity by Cyclization of Sialic Acid Moiety of Carbohydrate Ligands on Human Leukocytes . Proc. Natl. Acad. Sci. USA , 96 : 1597 – 1602 .
  • Kameyama , A. , Ehara , T. , Yamada , Y. , Ishida , H. , Kiso , M. and Hasegawa , A. 1995 . A Total Synthesis of Sialyl Dimeric Lex Ganglioside . J. Carbohydr. Chem. , 14 : 507 – 523 .
  • Hasegawa , A. , Hotta , K. , Kameyama , A. , Ishida , H. and Kiso , M. 1991 . Total Synthesis of Sialyl-α(2-6)-lactotetraosylceramide and Sialyl-α(2-6)-neolactotetraosylceramide . J. Carbohydr. Chem. , 10 : 439 – 459 .
  • Kiso , M. and Hasegawa , A. 1994 . “ Synthesis of Ganglioside GM3 and Analogs Containing Modified Sialic Acids and Ceramides ” . In Methods in Enzymology Edited by: Abelson , J. N. and Simon , M. I. Vol. 242 , 173 – 182 . San Diego : Academic Press .
  • Hasegawa , A. , Suzuki , N. , Ishida , H. and Kiso , M. 1996 . Synthesis of Ganglioside GM3 and GM4 Analogs Containing 2- or 3-Branched Fatty-Alkyl Residues in Place of Ceramide . J. Carbohydr. Chem. , 15 ( 5 ) : 623 – 637 .
  • Otsubo , N. , Ishida , H. and Kiso , M. 2001 . Synthesis of Novel Ganglioside GM4 Analogues Containing N-Deacetylated and Lactamized Sialic Acid: Probes for Searching New Ligand Structures for Human L-Selectin . Carbohydr. Res. , 330 ( 1 ) : 1 – 5 . The 1H NMR data (500 MHz, CD3OD) for N-deacetylated and lactamized sialic acid in the GM4 analogues are as follows: δ 1.71 (t, J = 12.1 Hz, H-3ax) and δ 2.87 (dd, Jgem = 12.5, J3,4 = 4.8 Hz, H-3eq) for the N-deacetylated sialic acid; δ 2.02 (dd, Jgem = 13.9, J3α,4 = 4.8 Hz, H-3α) and δ 2.29 (dd, Jgem = 13.9, J3β,4 = 10.3 Hz, H-3β) for the lactamized sialic acid. The FT-IR (KBr) spectrum showed a significant absorption band at 1690 cm−1 (lactam)

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