How useful is ferrocene as a scaffold for the design of β-sheet foldamers?

被引:48
作者
Chowdhury, Somenath [2 ]
Schatte, Gabriele [3 ]
Kraatz, Heinz-Bernhard [1 ]
机构
[1] Univ Western Ontario, Dept Chem, 1151 Richmond St, London, ON N6A 5B7, Canada
[2] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
[3] Univ Saskatchewan, Saskatchewan Struct Sci Ctr, Saskatoon, SK S7N 5C9, Canada
关键词
ferrocene; foldamers; molecular scaffolds; peptides; self-assembly;
D O I
10.1002/anie.200801460
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Crease crossing peptide embossing: The first tripeptide ferrocene foldamers to adopt an extended β-sheet-like structure in solution and solid state are presented. The flexibility of peptide substituents in 1,n′-ferrocene-bispeptide conjugates was thought to prevent the formation of extended β-sheet foldamers. The results suggest that ferrocene is a valuable scaffold for extended β-sheets. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7056 / 7059
页数:4
相关论文
共 36 条
[1]  
[Anonymous], ANGEW CHEM
[2]  
Aravinda S, 2002, ANGEW CHEM INT EDIT, V41, P3863, DOI 10.1002/1521-3773(20021018)41:20<3863::AID-ANIE3863>3.0.CO
[3]  
2-A
[4]  
Aravinda S., 2002, ANGEW CHEM, V114, P4019
[5]  
Balzani V, 2000, ANGEW CHEM INT EDIT, V39, P3348, DOI 10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO
[6]  
2-X
[7]   The first oligopeptide derivative of 1′-aminoferrocene-1-carboxylic acid shows helical chirality with antiparallel strands [J].
Barisic, L ;
Dropucic, M ;
Rapic, V ;
Pritzkow, H ;
Kirin, SI ;
Metzler-Nolte, N .
CHEMICAL COMMUNICATIONS, 2004, (17) :2004-2005
[8]   What vibrations tell us about proteins [J].
Barth, A ;
Zscherp, C .
QUARTERLY REVIEWS OF BIOPHYSICS, 2002, 35 (04) :369-430
[9]   Discovery of a pseudo β barrel:: Synthesis and formation by tiling of ferrocene cyclopeptides [J].
Chowdhury, S ;
Sanders, DAR ;
Schatte, G ;
Kraatz, HB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (05) :751-754
[10]   Amino acid conjugates of 1,1′-diaminoferrocene.: Synthesis and chiral organization [J].
Chowdhury, S ;
Mahmoud, KA ;
Schatte, G ;
Kraatz, HB .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (16) :3018-3023