Structure of (-)-neodysidenin from Dysidea herbacea.: Implications for biosynthesis of 5,5,5-trichloroleucine peptides

被引:36
作者
MacMillan, JB [1 ]
Trousdale, EK [1 ]
Molinski, TF [1 ]
机构
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
关键词
D O I
10.1021/ol006326u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Neodysidenin was isolated from the marine sponge Dysidea herbacea (Keller 1889) collected on the Great Barrier Reef. The complete configuration was obtained from a combination of methods, including capillary electrophoresis of Marfey's derivatives. Neodysidenin belongs to the L-series of trichloroleucine peptides, and the configuration of the N-methyl thiazolyl alanine residue (13R) is opposite to that of dysidenin.
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页码:2721 / 2723
页数:3
相关论文
共 22 条
[1]   REVISED ABSOLUTE-CONFIGURATION OF DYSIDENIN AND ISODYSIDENIN [J].
BISKUPIAK, JE ;
IRELAND, CM .
TETRAHEDRON LETTERS, 1984, 25 (28) :2935-2936
[2]   Synthetic studies of trichloroleucine marine natural products.: Michael addition of LiCCl3 to N-crotonylcamphor sultam [J].
Brantley, SE ;
Molinski, TF .
ORGANIC LETTERS, 1999, 1 (13) :2165-2167
[3]   DYSIDAMIDE, A NOVEL METABOLITE FROM A RED-SEA SPONGE DYSIDEA-HERBACEA [J].
CARMELY, S ;
GEBREYESUS, T ;
KASHMAN, Y ;
SKELTON, BW ;
WHITE, AH ;
YOSIEF, T .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (11) :1881-1888
[4]  
CHARLES C, 1978, TETRAHEDRON LETT, P1519
[5]   New chlorinated metabolites from the tropical marine sponge Dysidea herbacea [J].
Dumdei, EJ ;
Simpson, JS ;
Garson, MJ ;
Byriel, KA ;
Kennard, CHL .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (02) :139-144
[6]   New diketopiperazines from the sponge Dysidea chlorea [J].
Fu, X ;
Ferreira, MLG ;
Schmitz, FJ ;
Kelly-Borges, M .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (10) :1226-1231
[7]  
Hartung J, 1999, ANGEW CHEM INT EDIT, V38, P1209, DOI 10.1002/(SICI)1521-3773(19990503)38:9<1209::AID-ANIE1209>3.0.CO
[8]  
2-F
[9]   ISOLATION OF OSCILLATORIA-SPONGELIAE, THE FILAMENTOUS CYANOBACTERIAL SYMBIONT OF THE MARINE SPONGE DYSIDEA-HERBACEA [J].
HINDE, R ;
PIRONET, F ;
BOROWITZKA, MA .
MARINE BIOLOGY, 1994, 119 (01) :99-104
[10]   DYSIDIN, A NOVEL CHLORINE CONTAINING NATURAL PRODUCT FROM SPONGE DYSIDEA-HERBACEA [J].
HOFHEINZ, W ;
OBERHANSLI, WE .
HELVETICA CHIMICA ACTA, 1977, 60 (02) :660-669