Bioorganometallic tagging of N-acetylhistamine with an Fe(CO)3 unit: synthesis, X-ray structure, and protonation
Salah Merniz1, Louiza Himed2, Rofia Djerri2
1Institute of Industrial Hygiene and Safety, University of Batna 2, Batna, Algeria.
Abstract:
This study highlights the potential of organometallic carbonyl complexes as selective markers for biomolecules, enabling sensitive infrared (IR) detection. The regio- and stereoselective coupling of N-acetylhistamine, a histidine analogue, with the precursor complex 1 [Fe(CO)3(1,4-η5-N-pyridiniocyclohexa-1,3-diene)] BF4 affords the labeled complex 3 [Fe(CO)3(1,4-η5-N-acetylhistaminocyclohexa-1,3-diene)]. X-ray diffraction (XRD) confirms the exo stereochemistry and reveals a rigid, well-defined architecture. IR and 1H nuclear magnetic resonance spectroscopic studies combined with IR-monitored acid-base titration demonstrate the complex's stability in aqueous media between pH 5 and 8, alongside a modest increase in basicity relative to the free ligand. These findings establish the Fe(CO)3 moiety as a robust platform for selective labeling of peptides and proteins, paving the way for targeted applications in bioorganometallic chemistry and spectroscopic imaging.
More Related Videos
11:04Ion Mobility-Mass Spectrometry Techniques for Determining the Structure and Mechanisms of Metal Ion Recognition and Redox Activity of Metal Binding Oligopeptides
Published on: September 7, 2019
09:37Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Related Concept Videos
02:51Metal-Ligand Bonds
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
01:23Amines to Sulfonamides: The Hinsberg Test
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
01:23Properties of Organometallic Compounds
02:34Structural Isomerism
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...