Metallacyclopeptides: Artificial analogues of naturally occurring peptides

被引:40
作者
Albrecht, M [1 ]
Stortz, P [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
D O I
10.1039/b405660d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Naturally occurring metalloproteins contain metal ions either to introduce a special reactivity or to stabilize a peptide structure. Since the early 1990s, chemists have been trying to use metal coordination for the fixation of short artificial peptides in well-defined cyclic structures. In this tutorial review a survey of the general approaches towards metallacyclopeptides as small cyclic peptide derivatives or as a part of a bigger alpha-helix (or beta-sheet) structure is given. In three case studies it is shown how naturally occurring compounds can be mimicked by metal coordination to non-natural peptide derivatives.
引用
收藏
页码:496 / 506
页数:11
相关论文
共 46 条
[1]   Solid-phase synthesis of a double 4-pyridinyl terminated Leu-Ala-Leu tripeptide and macrocyclization by Palladium(II) coordination [J].
Albrecht, M ;
Stortz, P ;
Engeser, M ;
Schalley, CA .
SYNLETT, 2004, (15) :2821-2823
[2]   Preparation of tripeptide-bridged dicatechol Ligands and their macrocyclic molybdenum(VI) complexes: Fixation of the RGD sequence and the WKY sequence of urotensin II in a cyclic conformation [J].
Albrecht, M ;
Stortz, P ;
Runsink, J ;
Weis, P .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (15) :3657-3666
[3]   Mimicking the biologically active part of the cyclopeptides segetalin A and B by "clipping" of a linear tripeptide derivative by metal coordination [J].
Albrecht, M ;
Stortz, P ;
Weis, P .
SUPRAMOLECULAR CHEMISTRY, 2003, 15 (7-8) :477-483
[4]  
Albrecht M, 2003, SYNTHESIS-STUTTGART, P1307
[5]   Facile solid-phase synthesis of the WAGV-tetrapeptide front of the cyclopeptides segetalin A and B terminated by catechol moieties and formation of a metalla-cyclopeptide [J].
Albrecht, M ;
Stortz, P ;
Weis, P .
SYNLETT, 2003, (06) :867-869
[6]   The fixation of linear versus loop-type peptidic structures by metal coordination:: the coordination chemistry of Val-Val- and Val-Val-Val-bridged dicatechol ligands [J].
Albrecht, M ;
Spiess, O ;
Schneider, M ;
Weis, P .
CHEMICAL COMMUNICATIONS, 2002, (07) :786-787
[7]   Human urotensin-II is a potent vasoconstrictor and agonist for the orphan receptor GPR14 [J].
Ames, RS ;
Sarau, HM ;
Chambers, JK ;
Willette, RN ;
Alyar, NV ;
Romanic, AM ;
Louden, CS ;
Foley, JJ ;
Sauermelch, CF ;
Coatney, RW ;
Ao, ZH ;
Disa, J ;
Holmes, SD ;
Stadel, JM ;
Martin, JD ;
Liu, WS ;
Glover, GI ;
Wilson, S ;
McNulty, DE ;
Ellis, CE ;
Elshourbagy, NA ;
Shabon, U ;
Trill, JJ ;
Hay, DWP ;
Ohlstein, EH ;
Bergsma, DJ ;
Douglas, SA .
NATURE, 1999, 401 (6750) :282-286
[8]   ZINC-FINGER DOMAINS - FROM PREDICTIONS TO DESIGN [J].
BERG, JM .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :14-19
[9]   Metal-assembled modular proteins: Toward functional protein design [J].
Case, MA ;
Mclendon, GL .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (10) :754-762
[10]   Metal-directed assembly of cyclometallopeptides [J].
Constable, EC ;
Housecroft, CE ;
Mundwiler, S .
DALTON TRANSACTIONS, 2003, (11) :2112-2114