Synthesis and biological activities of lipid A-type pyrancarboxylic acid derivatives

Authors
Mochizuki, T Iwano, Y Shiozaki, M Kurakata, S Kanai, S Nishijima, M
Citation
T. Mochizuki et al., Synthesis and biological activities of lipid A-type pyrancarboxylic acid derivatives, CARBOHY RES, 324(4), 2000, pp. 225-230
Citations number
13
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
CARBOHYDRATE RESEARCH
ISSN journal
00086215 → ACNP
Volume
324
Issue
4
Year of publication
2000
Pages
225 - 230
Database
ISI
SICI code
0008-6215(20000310)324:4<225:SABAOL>2.0.ZU;2-P
Abstract
The synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing part of th e disaccharide instead of the phosphate group in lipid A, is described. One of the compounds thus synthesized, which has an acyl substitution pattern similar to that of Escherichia coli lipid A, showed lipopolysaccharide (LPS )-agonistic activity. The other, which contains four lipid chains in the mo lecule, exhibited strong LPS-antagonistic activity toward human monoblastic U937 cells. (C) 2000 Elsevier Science Ltd. All rights reserved.