Efficient Reagent-Saving Method for the N-Terminal Labeling of Bioactive Peptides with Organometallic Carboxylic Acids by Solid-Phase Synthesis

被引：13

作者：

Slootweg, Jack C. ^{[1
,3
]}

Albada, H. Bauke ^{[2
,3
]}

Siegmund, Daniel ^{[3
]}

Metzler-Nolte, Nils ^{[3
]}

机构：

[1] Mercachem, Kerkenbos 1013, NL-6546 BB Nijmegen, Netherlands

[2] Wageningen Univ & Res, Organ Chem Lab, Stippeneng 4, NL-6708 WE Wageningen, Netherlands

[3] Ruhr Univ Bochum, Fak Chem & Biochem, Lehrstuhl Anorgan Chem Bioanorgan Chem 1, D-44801 Bochum, Germany

来源：

ORGANOMETALLICS | 2016年 / 35卷 / 18期

关键词：

ANTIBACTERIAL PEPTIDES; RUTHENOCENE; FERROCENE; CHEMISTRY; LIGANDS; KETONES; SCAN;

D O I：

10.1021/acs.organomet.6b00544

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Labeling of biomolecules with organometallic moieties holds great promise as a tool for chemical biology and for the investigation of biochemical signaling pathways. Herein, we report a robust and reproducible synthetic strategy for the synthesis of ruthenocenecarboxylic acid, giving the acid in 53% overall yield. This organometallic label was conjugated via solid phase peptide synthesis in near-quantitative yield to a number of different biologically active peptides, using only 1 equiv of the acid and coupling reagents, thereby avoiding wasting the precious organometallic acid. This optimized method of stoichiometric N-terminal acylation was then also successfully applied to conjugating ferrocenecarboxylic acid and a novel organometallic Re-I(CO)(3) complex, showing the generality of the synthetic procedure.

引用

页码：3192 / 3196

页数：5

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