Synthesis of neoglycosphingolipid from methoxyamino-functionalized ceramide

An efficient approach for the synthesis of a methoxyamino- functionalized ceramide was established from phytosphingosine using specific Nb -> Na acyl migration of the octadecanoyl group during the removal of Na-Fmoc protective group. One step glycoblotting reaction of the ceramide mimic with lact...

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Bibliographic Details
Published inBioorganic & medicinal chemistry letters Vol. 24; no. 4; pp. 1197 - 1200
Main Authors Ishida, Junya, Hinou, Hiroshi, Naruchi, Kentaro, Nishimura, Shin-Ichiro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 15.02.2014
Subjects
Ceramides - chemistry
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Dose-Response Relationship, Drug
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Glycoside Hydrolases - antagonists & inhibitors
Glycoside Hydrolases - metabolism
Glycosphingolipids - chemical synthesis
Glycosphingolipids - chemistry
Glycosphingolipids - pharmacology
Hydroxylamines - chemistry
Life Sciences & Biomedicine
Molecular Conformation
Pharmacology & Pharmacy
Physical Sciences
Recombinant Proteins - metabolism
Rhodococcus
Rhodococcus - enzymology
Science & Technology
Structure-Activity Relationship
Acyl migration
GLYCOSIDASE
DESIGN
ACID
CLEAVES
ENDOGLYCOCERAMIDASE
Neoglycosphingolipid
Glycoblotting
Ceramide
Oxime
OLIGOSACCHARIDE
LINKAGE
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Summary:An efficient approach for the synthesis of a methoxyamino- functionalized ceramide was established from phytosphingosine using specific Nb -> Na acyl migration of the octadecanoyl group during the removal of Na-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. (C) 2014 Elsevier Ltd. All rights reserved.
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ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2013.12.091