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Biological activities of chemically synthesized analogues of the nonreducing sugar moiety of lipid A
Author(s) -
Matsuura Motohiro,
Kojima Yasuhiko,
Yuzuru Homma J.,
Kubota Yoshiyuki,
Yamamoto Akihiro,
Kiso Makoto,
Hasegawa Akira
Publication year - 1984
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(84)80131-3
Subject(s) - chemistry , lipid a , biological activity , glucosamine , acylation , biochemistry , lipid metabolism , moiety , enzyme , stereochemistry , sugar , tumor necrosis factor alpha , structure–activity relationship , bacteria , in vitro , biology , immunology , genetics , catalysis
Biological activities of five synthetic lipid A analogues (D‐glucosamine derivatives) were examined to elucidate the structure required for expression of the biological activities of endotoxin. Proclotting enzyme of horseshoe crab activation, interferon‐inducing and tumor necrosis factor‐inducing activities were significantly expressed by an analogue which possesses 4‐ O ‐phosphoryl, 3‐ O ‐tetradecanoyl and N ‐tetradecanoyloxytetradecanoyl groups. The results obtained with different analogues show that the 4‐ O ‐phosphoryl and N ‐tetradecanoyloxytetradecanoyl groups are important for expression of the above activities. The effect of 6‐ O ‐acylation in preventing the expression of these biological activities is also suggested. Pyrogenic activity was not detected in any of the compounds tested.