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Partial Synthesis of a Sea Cucumber Ganglioside Analogue from a Starfish Cerebroside
Author(s) -
Higuchi Ryuichi,
Mori Takeshi,
Sugata Tetsuji,
Yamada Koji,
Miyamoto Tomofumi
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199901)1999:1<145::aid-ejoc145>3.0.co;2-e
Subject(s) - cerebroside , chemistry , starfish , sea cucumber , ganglioside , stereochemistry , glucocerebroside , derivative (finance) , fatty acid , biochemistry , enzyme , glucocerebrosidase , ecology , financial economics , economics , biology
A sea cucumber ganglioside analogue 7 (NGNAα2→ 6Glcβ1→1Cer), which contains a phytosphingosine as a long‐chain base and an α‐hydroxy fatty acid, has been synthesized. Coupling of the methyl 2‐thioglycoside derivative 5 of N ‐glycolylneuraminic acid with a cerebroside derivative 3 , prepared from acanthacerebroside A ( 1 ), afforded protected ganglioside analogue 6 , which was deprotected to give the corresponding ganglioside 7 .