Ferrocene-dipeptide conjugates derived from aminoferrocene and 1-acetyl-1′-aminoferrocene: synthesis and conformational studies

被引：22

作者：

Kovac, Veronika ^{[1
]}

Semencic, Mojca Cakic ^{[1
]}

Kodrin, Ivan ^{[2
]}

Roca, Suncica ^{[3
]}

Rapic, Vladimir ^{[1
]}

机构：

[1] Univ Zagreb, Fac Food Technol & Biotechnol, Zagreb 10000, Croatia

[2] Fac Sci, Dept Chem, Zagreb 10000, Croatia

[3] Rudjer Boskovic Inst, NMR Ctr, Zagreb 10000, Croatia

来源：

TETRAHEDRON | 2013年 / 69卷 / 48期

关键词：

Ferrocene peptide; Conformational analysis; Hydrogen bonds; Induced circular dichroism; DFT calculations; AMINO-ACIDS; 1'-AMINOFERROCENE-1-CARBOXYLIC ACID; CHIRALITY ORGANIZATION; PEPTIDES; SYSTEM; CHAINS; TURNS;

D O I：

10.1016/j.tet.2013.09.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study we present the synthesis and conformational analysis of mono- and disubstituted ferrocene bioconjugates bearing dipeptide chains (Boc-AA-AA-Fn-X, AA=Gly, L-Val). The conformational preferences of novel aminoferrocene derived conjugates with X=H, as well as their 1-acetyl analogues (X=COMe), were investigated by spectroscopic techniques (IR, NMR and CD) and corroborated by DFT calculations. Chirally organized structures, stabilized through intrachain hydrogen bonds, prevail in solution when X=H. The resulting 10-membered hydrogen-bond ring is destabilized by heteroannular introduction of an acetyl group when X=COMe. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：10497 / 10506

页数：10

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