Structure and total synthesis of cyclodidemnamide B, a cycloheptapeptide from the ascidian Didemnum molle

被引:14
作者
Arrault, A [1 ]
Witczak-Legrand, A [1 ]
Gonzalez, P [1 ]
Bontemps-Subielos, N [1 ]
Banaigs, B [1 ]
机构
[1] Univ Perpignan, UMR 5054 CNRS, Ctr Phytopharm, F-66860 Perpignan, France
关键词
cycloheptapeptide; thiazole-containing peptide; ascidian; Didemnum molle;
D O I
10.1016/S0040-4039(02)00693-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new cycloheptapeptide. cyclodidemnamide B (1), has been isolated from the marine ascidian Didemnum molle, collected at Ibo island, Mozambique. The structure of the bisthiazole-containing macrocyclic peptide was initially assigned using 2D NMR analysis and data comparisons with cyclodidemnamide. The absolute configuration was deduced after hydrolysis and characterization of degradation residues by chiral HPLC analysis. The total synthesis served as an unambiguous structural and stereochemical proof. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4041 / 4044
页数:4
相关论文
共 13 条
[1]   Total synthesis and assignment of configuration of the thiazoline-based cyclopeptide cyclodidemnamide isolated from the sea squirt Didemnum molle [J].
Boden, CDJ ;
Norley, M ;
Pattenden, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (06) :883-888
[2]   Total syntheses and re-assignment of configurations of the cyclopeptides lissoclinamide 4 and lissoclinamide 5 from Lissoclinum patella [J].
Boden, CDJ ;
Pattenden, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (06) :875-882
[3]   STUDIES OF AUSTRALIAN ASCIDIANS .4. MOLLAMIDE, A CYTOTOXIC CYCLIC HEPTAPEPTIDE FROM THE COMPOUND ASCIDIAN DIDEMNUM MOLLE [J].
CARROLL, AR ;
BOWDEN, BF ;
COLL, JC ;
HOCKLESS, DCR ;
SKELTON, BW ;
WHITE, AH .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (01) :61-69
[4]   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
[5]   Total synthesis of mollamide, a reverse prenyl substituted cytotoxic cyclic peptide from Didemnum molle [J].
McKeever, B ;
Pattenden, G .
TETRAHEDRON LETTERS, 1999, 40 (52) :9317-9320
[6]   Total synthesis and revision of stereochemistry of cyclodidemnamide, a novel cyclopeptide from the marine ascidian Didemnum molle [J].
Norley, MC ;
Pattenden, G .
TETRAHEDRON LETTERS, 1998, 39 (19) :3087-3090
[7]   Four new cytotoxic cyclic hexa- and heptapeptides from the marine ascidian Didemnum molle [J].
Rudi, A ;
Aknin, M ;
Gaydou, EM ;
Kashman, Y .
TETRAHEDRON, 1998, 54 (43) :13203-13210
[8]  
Stanchev M, 1999, ARCH PHARM, V332, P297, DOI 10.1002/(SICI)1521-4184(19999)332:9<297::AID-ARDP297>3.3.CO
[9]  
2-R
[10]   CYCLODIDEMNAMIDE - A NEW CYCLIC HEPTAPEPTIDE FROM THE MARINE ASCIDIAN DIDEMNUM MOLLE [J].
TOSKE, SG ;
FENICAL, W .
TETRAHEDRON LETTERS, 1995, 36 (46) :8355-8358