The absolute stereochemistry of kahalalide F

被引:28
作者
Goetz, G [1 ]
Yoshida, WY [1 ]
Scheuer, PJ [1 ]
机构
[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA
关键词
antitumor compounds; depsipeptides; marine metabolites; stereochemistry;
D O I
10.1016/S0040-4020(99)00410-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Kahalalide F (1) is a depsipeptide of 14 residues, five of which form a 19-membered ring. It was isolated from a marine mollusk, Elysia rufescens, and is currently in preclinical trials against lung and colon cancers. It was known from conventional amino acid analysis that five valine and two threonine residues represented D- and L- enantiomers, but their position in the molecule was not known. After extensive hydrolytic trials, a combination of acid hydrolysis and hydrazinolysis succeeded in definitive stereochemical assignment. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7739 / 7746
页数:8
相关论文
共 6 条
[1]   Two acyclic kahalalides from the sacoglossan mollusk Elysia rufescens [J].
Goetz, G ;
Nakao, T ;
Scheuer, PJ .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (06) :562-567
[2]   KAHALALIDE-F - A BIOACTIVE DEPSIPEPTIDE FROM THE SACOGLOSSAN MOLLUSK ELYSIA-RUFESCENS AND THE GREEN-ALGA BRYOPSIS SP [J].
HAMANN, MT ;
SCHEUER, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) :5825-5826
[3]   Kahalalides: Bioactive peptide from a marine mollusk Elysia rufescens and its algal diet Bryopsis sp [J].
Hamann, MT ;
Otto, CS ;
Scheuer, PJ ;
Dunbar, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6594-6600
[4]  
KAHALALIDE F, Patent No. 9127225
[5]   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
[6]  
Schroeder W A, 1972, Methods Enzymol, V25, P138, DOI 10.1016/S0076-6879(72)25011-X