Synthetic Studies on Selectin Ligands/Inhibitors: Synthesis and Biological Activity of the Sulfated and Phosphorylated Multivalent β-D-Galactopyranosides Containing Fatty Alkyl Residues12
作者:
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,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1998)
卷期:
Volume 17,
issue 4-5
页码: 499-518
ISSN:0732-8303
年代: 1998
DOI:10.1080/07328309808002333
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Ten sulfated and three phosphorylated β-D-galactopyranoside dimers and one sulfated β-D-galactopyranoside trimer containing fatty alkyl residues in place of ceramide have been synthesized. The coupling of 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (2) with branched fatty alkyl diols and a triol (1a-1j) using mercury bromide as an activating agent gave the corresponding parent glycolipids (4a-4j) in good yields. Regioselective sulfation of these parent glycolipids through the dibutylstannylene acetals produced the target sulfated glycolipids, 3-sulfate (5a-5j) while stepwise phosphorylation with dibenzyloxy(diisopropylamino) phosphine gave the phosphorylated glycolipids, 3,4-bisphosphate (9e, g, i). The synthetic glycolipids were assayed for their ability to block the adhesion of HL-60 cells to immobilized P-, L- and E-selectin.
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