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Biologically active glycosides from asteroidea, XXVI. Stereochemistry of the four diastereomers of ceramide and ceramide lactoside
Author(s) -
Sugiyama Shigeo,
Honda Masanori,
Higuchi Ryuichi,
Komori Tetsuya
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910161
Subject(s) - ceramide , diastereomer , chemistry , stereochemistry , hydrolysis , glycoside , biochemistry , apoptosis
The diastereomeric ceramides, (2 S ,3 S ,4 R )‐, (2 S ,3 S ,4 S )‐, (2 S ,3 R ,4 S )‐, and (2 S ,3 R ,4 R )‐2‐[(2 R )‐2‐hydroxytetracosanoylamino]‐1,3,4‐hexadecanetriols 5–8 and the corresponding ceramide lactosides 1–4 have been synthesized. Compound 1 is almost identical with the natural specimen, acanthalactoside A. The physical data of these diastereomeric compounds are most useful to determine the stereochemistry of ceramides and ceramide lactosides, either isolated from natural sources or obtained by partial hydrolysis of gangliosides.