Synthesis of ceramidated GLA-60 derivatives.
Ceramidated GLA-60 derivatives 11 and 11' were synthesized from 1 via glycosidation of ceramide derivative 12 as a glycosyl acceptor with GLA-60 derivative 5 as a glycosyl donor, and successive conversion. Compound 11' showed only weak LPS-antagonistic activity without showing any LPS-agonistic activity.
Nakamura
Tsuyoshi
T
Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd., Hiromachi 1-2-58, Shinagawa-ku, Tokyo 140-8710, Japan.
Shiozaki
Masao
M
Kurakata
Shin-ichi
S
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry; D002518:Ceramides / Q000737:chemistry*; D008050:Lipid A / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared
D000276:Adjuvants, Immunologic; D002518:Ceramides; D008050:Lipid A; C056260:GLA 60