Bioorganometallic Chemistry - Transition Metal Complexes withα-Amino Acids and Peptides

Abstract

A new, interdisciplinary research area has emerged known as bioorganometallic chemistry. It focuses on the introduction of organometallic fragments into biomolecules (see, for example, structure on the right). "Classical" α-amino acid and peptide ligands have proven particularly versatile, and provide access to compounds that display interesting stereochemistry. α-Amino acids and peptides can be synthesized, labeled, stabilized, or activated by organometallic fragments.

Transition metal bioconjugates with an organometallic link between the metal and the biomolecular scaffold

“…It is thus not surprising that this area of bioorganometallic chemistry has seen substantial progress. A 1998 review on transition metal complexes with α-amino acids and peptides reflects the early interest in using these natural compounds in transition metal chemistry [54]. In most cases, the biomolecule binds to the metal centre via a heteroatom that is naturally located in the peptidic backbone, in the side chains of the amino acids, or available after insertion of an extra coordination site [55].…”

Induced-fit recognition of DNA by organometallic complexes with dynamic stereogenic centers

“…For example, Jaouen et al (2) have designed antiestrogenic cyclopentadienyl complexes that recognize the estrogen receptor and have potential for treatment of breast cancer, and other workers have also carried out pioneering studies on the recognition of nucleobases, amino acids, and peptides by organometallic centers (1,(3)(4)(5). However, as far as we are aware, there are few investigations of specific interactions of organometallic arene complexes with natural DNA (6).…”

“…The biological chemistry of Ru( 6 -arene) complexes is relatively unexplored, although there are many reports of their use as chiral catalysts (7)(8)(9) or as synthetic reagents for peptide synthesis (3). We have discovered the anticancer potential of the ethylenediamine (en) complexes [( 6 -arene)RuCl(en)] ϩ , which exhibit in vitro and in vivo activity, for example in a cisplatin-resistant A2780 xenograft model of human ovarian cancer (10,11).…”

A Novel Field of Research: Bioorganometallic Chemistry, Origins, and Founding Principles

“…For a comprehensive review on ferrocenyl bioorganometallics see [207]. The pioneering work of Schlögl was later developed by Sergheraert and Tartar [208] and others [7,209]. Hieber et al [210] used the halo-bridged complex [M(NO) 2 Br] 2 with amino acids for the synthesis of the corresponding N,O-aminocarboxylates.…”

“…CO, alkyls, π-bonded species) or biomolecules (steroids, amino acids, sugars, peptides, DNA, vitamins, enzymes, antibodies) attached by direct metalcarbon linkages, but all having in common their ability to play a role in biological processes. This by no means exhaustive list should give an idea of the potential scope of this field [3][4][5][6][7][8][9][10][11][12][13][14][15].…”