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Determination of the Absolute Configuration at the Two Cyclopropane Moieties of Plakoside A, an Immunosuppressive Marine Galactosphingolipid
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2002
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Bioorganic ChemistryAbsolute ConfigurationBiochemistryEngineeringNatural SciencesGlycobiologyPrenylated GalactosphingolipidPlakoside AImmunosuppressive Marine GalactosphingolipidMarine BiologyPharmacologyCarbohydrate-protein InteractionBiomolecular EngineeringGlycosylation
Plakoside A (1) {(2S,3R,11R*,12S*)-2-[(2′′′R,5′′′Z,11′′′R*, 12′′′S*)-2′′′-hydroxy-11′′′,12′′′-methylene-5′′′-docosenamido]-1-O-[2′-O-(3′′-methyl-2′′-butenyl)-β-D-galactopyranosyl]-11,12-methylene-1,3-docosanediol} is a prenylated galactosphingolipid isolated as an immunosuppressant from the marine sponge Plakortis simplex. The absolute configuration of plakoside A was determined as 11S,12R,11′′′S,12′′′R by its degradation to two cyclopropane-containing fatty acids 2a and 3a followed by their derivatization with a chiral reagent 4 and subsequent HPLC analysis of the resulting derivatives 2b and 3b. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)