Metal–Carbon Bonds in Biopolymer Conjugates: Bioorganometallic Nucleic Acid Chemistry

Abstract

This review summarizes the field of bioorganometallic nucleic acid chemistry, with a specific focus on various synthetic approaches for utilizing organometallic groups, in particular ferrocene, as functional tags for existing nucleic acids or as components for novel nucleic acid analogues.

Ferrocenyl GNA Nucleosides: A Bridge between Organic and Organometallic Xeno‐nucleic Acids

“…The ferrocenyl moiety adopts an eclipsed conformation with the average C1−Mp1−Mp2−C6 (Mp=midpoint of the cyclopentadienyl ligand) angles of −1.13° and 0.81° for ( S , R )‐ 2 and ( R , S )‐ 2 , respectively. The geometry of the methylated thymine does not show significant differences compared with the literature . In both structures the methylated thymine moiety points away from the ferrocenyl group.…”

“…The first relies on chemical or enzymatic oligomerization/incorporation of ferrocenyl nucleosides into the biopolymer and the second uses postsynthetic incorporation of ferrocenyl moieties into oligonucleotide strands. These strategies have been discussed in an excellent review . The development of ferrocenyl XNA nucleosides and nucleic acids is a hot topic in chemistry.…”

The Effects of Magnesium Ions on the Enzymatic Synthesis of Ligand-Bearing Artificial DNA by Template-Independent Polymerase

“…Over recent decades, a sustained effort has been devoted to the development of artificial metal-mediated base pairs, which are formed through metal coordination bonding instead of hydrogen bonding [ 4 , 5 ]. Metal coordination is one of the most employed interactions for designing the self-assembly of molecules [ 6 ] and thus has been also utilized for the construction of DNA-based materials [ 7 , 8 , 9 ]. Metallo-base pairs, consisting of two ligand-bearing nucleosides and a bridging metal ion, have unique and fascinating characteristics as noted below.…”

Luminescent fac-[Re(CO)3(phen)] carboxylato complexes with non-steroidal anti-inflammatory drugs: synthesis and mechanistic insights into the in vitro anticancer activity of fac-[Re(CO)3(phen)(aspirin)]

“…anticancer or antibacterial) properties. Thus, metal-containing moieties have been conjugated to a number of biological vectors including peptides, 16 steroid hormones, 17 nucleobases and nucleotides, 18,19 and secondary natural products. 20 Synthetic drugs have also attracted great attention as targets for metal conjugation.…”