Concise synthesis of stereodefined, thiazole -: containing cyclic hexa- and octapeptide relatives of the Lissoclinums, via cyclooligomerisation reactions

被引:36
作者
Bertram, A [1 ]
Blake, AJ [1 ]
de Turiso, FGL [1 ]
Hannam, JS [1 ]
Jolliffe, KA [1 ]
Pattenden, G [1 ]
Skae, M [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
关键词
Lissoclinum; cyclooligomerisation; thiazole;
D O I
10.1016/S0040-4020(03)00821-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a range of thiazole containing cyclic peptides using cyclooligomerisation reactions of amino acid substituted thiazole monomers and by macrolactamisation procedures is reported. The synthetic approaches lead to high yields of novel 18- and 24-membered ring analogues of the naturally occurring Lissoclinum families of cyclic peptides found in marine organisms and algae. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6979 / 6990
页数:12
相关论文
共 40 条
[11]   THE CHIRAL SYNTHESIS OF THIAZOLE AMINO-ACID ENANTIOMERS [J].
BREDENKAMP, MW ;
HOLZAPFEL, CW ;
VANZYL, WJ .
SYNTHETIC COMMUNICATIONS, 1990, 20 (15) :2235-2249
[12]   REFINEMENT OF ANGULAR DEPENDENCE OF PEPTIDE VICINAL NH-C ALPHA H COUPLING-CONSTANT [J].
BYSTROV, VF ;
IVANOV, VT ;
PORTNOVA, SL ;
BALASHOVA, TA ;
OVCHINNIKOV, YA .
TETRAHEDRON, 1973, 29 (06) :873-877
[13]   PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE - A NEW EFFICIENT COUPLING REAGENT IN PEPTIDE CHEMISTRY [J].
CHEN, SQ ;
XU, JC .
TETRAHEDRON LETTERS, 1991, 32 (46) :6711-6714
[14]   Conformations of cyclic octapeptides and the influence of heterocyclic ring constraints upon calcium binding [J].
Cusack, RM ;
Grondahl, L ;
Abbenante, G ;
Fairlie, DP ;
Gahan, LR ;
Hanson, GR ;
Hambley, TW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (02) :323-331
[15]   Cyclic octapeptides containing thiazole. Effect of stereochemistry and degree of flexibility on calcium binding properties [J].
Cusack, RM ;
Grondahl, L ;
Fairlie, DP ;
Gahan, LR ;
Hanson, GR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2002, (03) :556-563
[16]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[17]   NEW CYCLIC-PEPTIDES WITH CYTO-TOXIC ACTIVITY FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].
DEGNAN, BM ;
HAWKINS, CJ ;
LAVIN, MF ;
MCCAFFREY, EJ ;
PARRY, DL ;
VANDENBRENK, AL ;
WATTERS, DJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1349-1354
[18]   Marine metabolites and metal ion chelation. Circular dichroism studies of metal binding to Lissoclinum cyclopeptides [J].
Freeman, DJ ;
Pattenden, G ;
Drake, AF ;
Siligardi, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (01) :129-135
[19]   Interaction of zinc(II) with the cyclic octapeptides, cyclo[Ile(Oxn)-D-Val(Thz)]2 and ascidiacyclamide, a cyclic peptide from Lissoclinum patella [J].
Grondahl, L ;
Sokolenko, N ;
Abbenante, G ;
Fairlie, DP ;
Hanson, GR ;
Gahan, LR .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (08) :1227-1234
[20]   NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .51. A SYNTHESIS OF ASCIDIACYCLAMIDE, A CYTO-TOXIC CYCLIC PEPTIDE FROM ASCIDIAN - DETERMINATION OF ITS ABSOLUTE-CONFIGURATION [J].
HAMADA, Y ;
KATO, S ;
SHIOIRI, T .
TETRAHEDRON LETTERS, 1985, 26 (27) :3223-3226