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
[11]  
KAZLAUSKAS R, 1977, TETRAHEDRON LETT, P3183
[12]   HERBACEAMIDE, A CHLORINATED N-ACYL AMINO ESTER FROM THE MARINE SPONGE, DYSIDEA-HERBACEA [J].
LEE, GM ;
MOLINSKI, TF .
TETRAHEDRON LETTERS, 1992, 33 (50) :7671-7674
[13]   Herbacic acid, a simple prototype of 5,5,5-trichloroleucine metabolites from the sponge Dysidea herbacea [J].
MacMillan, JB ;
Molinski, TF .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (01) :155-157
[14]   DETERMINATION OF D-AMINO ACIDS .2. USE OF A BIFUNCTIONAL REAGENT, 1,5-DIFLUORO-2,4-DINITROBENZENE [J].
MARFEY, P .
CARLSBERG RESEARCH COMMUNICATIONS, 1984, 49 (06) :591-596
[15]  
MOLINSKI TF, UNPUB
[16]   Biosynthesis of the marine cyanobacterial metabolite barbamide. 1. Origin of the trichloromethyl group [J].
Sitachitta, N ;
Rossi, J ;
Roberts, MA ;
Gerwick, WH ;
Fletcher, MD ;
Willis, CL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (28) :7131-7132
[17]   FREE SOLUTION CAPILLARY ELECTROPHORESIS AND MICELLAR ELECTROKINETIC RESOLUTION OF AMINO-ACID ENANTIOMERS AND PEPTIDE ISOMERS WITH L-MARFEYS AND D-MARFEYS REAGENTS [J].
TRAN, AD ;
BLANC, T ;
LEOPOLD, EJ .
JOURNAL OF CHROMATOGRAPHY, 1990, 516 (01) :241-249
[18]   Reductive dechlorination of dysidenin from Dysidea herbacea. Structure of a novel binuclear zinc metallocycle [J].
Trousdale, EK ;
Taylor, SW ;
Parkin, S ;
Hope, H ;
Molinski, TF .
NATURAL PRODUCT LETTERS, 1998, 12 (01) :61-66
[19]   NEW POLYCHLORINATED AMINO-ACID DERIVATIVES FROM THE MARINE SPONGE DYSIDEA-HERBACEA [J].
UNSON, MD ;
ROSE, CB ;
FAULKNER, DJ ;
BRINEN, LS ;
STEINER, JR ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) :6336-6343
[20]   CYANOBACTERIAL SYMBIONT BIOSYNTHESIS OF CHLORINATED METABOLITES FROM DYSIDEA-HERBACEA (PORIFERA) [J].
UNSON, MD ;
FAULKNER, DJ .
EXPERIENTIA, 1993, 49 (04) :349-353