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Synthesis of a Prenylated and Immunosuppressive Marine Galactosphingolipid with Cyclopropane‐Containing Alkyl Chains: (2 S ,3 R ,11 S ,12 R ,2′′′ R ,5′′′ Z ,11′′′ S ,12′′′ R )‐Plakoside A and Its (2 S ,3 R ,11 R ,12 S ,2′′′ R ,5′′′ Z ,11′′′ R ,12′′′ S ) Isomer
Author(s) -
Seki Masanori,
Mori Kenji
Publication year - 2001
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(200110)2001:20<3797::aid-ejoc3797>3.0.co;2-y
Subject(s) - sponge , chemistry , prenylation , stereochemistry , cyclopropane , methylene , sphingosine , alkyl , medicinal chemistry , organic chemistry , biochemistry , ring (chemistry) , botany , enzyme , biology , receptor
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 . (2 S ,3 R ,11 S ,12 R ,2′′′ R ,5′′′ Z ,11′′′ S ,12′′′ R )‐Plakoside A ( 1 ) has been synthesized by combining the sphingosine part 16 , the α‐hydroxy acid part 28 , and the prenylated sugar part 33 . (2 S ,3 R ,11 R ,12 S ,2′′′ R ,5′′′ Z ,11′′′ R ,12′′′ S )‐Plakoside A ( 1′ ) has also been synthesized.