Determination of the absolute configuration at the two cyclopropane moieties of plakoside A, an immunosuppressive marine galactosphingolipid

The absolute configuration of plakoside A {(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)-beta-D-galactopyranosyl]-11,12-methylene-1,3-docosanediol} was determined as 11S,12R,11'''S,12'''R by its degradation to two cyclopropane-containing fatty acids followed by their derivatization with a chiral reagent and subsequent HPLC analysis of the resulting derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.