Incorporation of the unnatural organometallic amino acid 1′-aminoferrocene-1-carboxylic acid (Fca) into oligopeptides by a combination of Fmoc and Boc solid-phase synthetic methods

被引：58

作者：

Barisic, Lidija

Rapic, Vladimir

Metzler-Nolte, Nils

机构：

[1] Univ Bochum, Dept Chem, D-44801 Bochum, Germany

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

[3] Heidelberg Univ, Inst Pharm & Mol Biotechnol, D-69120 Heidelberg, Germany

来源：

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY | 2006年 / 20期

关键词：

bioorganometallic chemistry; ferrocene; peptides; solid-phase peptide synthesis; unnatural amino acids;

D O I：

10.1002/ejic.200600534

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The organometallic amino acid 1'-aminoferrocene-1-carboxylic acid (Fca) was incorporated internally into a peptide sequence by solid-phase methods combining natural Fmoc-protected amino acids and Boc-Fca-OH to give the pentapeptide Boc-Fca-Ala-Gly-Val-Leu-NH2 (2) and the octapeptide Ac-Val-Gly-Ala-Fca-Ala-Gly-Val-Leu-NH2 (3). Compound 3 was found to have a helically ordered structure by NMR and CD spectroscopy, which is stabilized by intramolecular hydrogen bonding in an antiparallel beta-sheet-like arrangement. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).

引用

页码：4019 / 4021

页数：3

共 31 条

[1] The first oligopeptide derivative of 1′-aminoferrocene-1-carboxylic acid shows helical chirality with antiparallel strands [J].