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Determination of the Absolute Configuration at the Two Cyclopropane Moieties of Plakoside A, an Immunosuppressive Marine Galactosphingolipid
Author(s) -
Tashiro Takuya,
Akasaka Kazuaki,
Ohrui Hiroshi,
Fattorusso Ernesto,
Mori Kenji
Publication year - 2002
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 - 10.1002/1099-0690(200211)2002:21<3659::aid-ejoc3659>3.0.co;2-u
Subject(s) - cyclopropane , chemistry , absolute configuration , sponge , derivatization , methylene , reagent , stereochemistry , derivative (finance) , absolute (philosophy) , cyclopropanation , high performance liquid chromatography , organic chemistry , ring (chemistry) , catalysis , botany , financial economics , economics , biology , philosophy , epistemology
Plakoside A ( 1 ) {(2 S ,3 R ,11 R *,12 S *)‐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 11 S ,12 R ,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)