Synthesis of neoglycosphingolipid from methoxyamino-functionalized ceramide.
An efficient approach for the synthesis of a methoxyamino-functionalized ceramide was established from phytosphingosine using specific Nβ→Nα acyl migration of the octadecanoyl group during the removal of Nα-Fmoc protective group. One step glycoblotting reaction of the ceramide mimic with lactose afforded a neoglycosphingolipid showing potent inhibitory activity against recombinant endoglycoceramidase II from Rhodococcus sp.
Graduate School of Life Science and Faculty of Advanced Life Science, Hokkaido University, N21, W11, Kita-ku, Sapporo 001-0021, Japan.
Junya
J
Ishida
Graduate School of Life Science and Faculty of Advanced Life Science, Hokkaido University, N21, W11, Kita-ku, Sapporo 001-0021, Japan; Medicinal Chemistry Pharmaceuticals Co. Ltd., N21, W12, Sapporo 001-0021, Japan.
Hiroshi
H
Hinou
Medicinal Chemistry Pharmaceuticals Co. Ltd., N21, W12, Sapporo 001-0021, Japan.
Kentaro
K
Naruchi
Graduate School of Life Science and Faculty of Advanced Life Science, Hokkaido University, N21, W11, Kita-ku, Sapporo 001-0021, Japan; Medicinal Chemistry Pharmaceuticals Co. Ltd., N21, W12, Sapporo 001-0021, Japan. Electronic address: shin@sci.hokudai.ac.jp.
Shin-Ichiro
S
Nishimura
D002518:Ceramides / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006028:Glycosphingolipids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006898:Hydroxylamines / Q000737:chemistry*; D008968:Molecular Conformation; D011994:Recombinant Proteins / Q000378:metabolism; D012240:Rhodococcus / Q000201:enzymology; D013329:Structure-Activity Relationship
D002518:Ceramides; D004791:Enzyme Inhibitors; D006028:Glycosphingolipids; D006898:Hydroxylamines; D011994:Recombinant Proteins; C005214:methoxyamine; D006026:Glycoside Hydrolases; C050427:endoglycoceramidase
Acyl migration; Ceramide; Glycoblotting; Neoglycosphingolipid; Oxime