Modular assembly of novel DNA-based catalysts

Abstract

A novel modular strategy towards the assembly of DNA-based catalysts containing a covalently anchored metal complex is presented.

Asymmetric Catalysis with Helical Polymers

“…This strategy involves two oligonucleotides, ON1 and ON2, with a covalently attached 2,2'-bipyridine ligand at the terminus of one of the strands (Scheme 16). [40] Upon hybridization of both oligonucleotides with a complementary template strand, the catalytic moiety is placed in an internal position in the DNA duplex. Complexation of Cu 2 + to the bipyridine moiety produced the DNA-based catalyst, which was found to be active in the asymmetric Diels-Alder reaction of azachalcone with cyclopentadiene.…”

“…[39,40] The Diels-Alder reaction of azachalcone with cyclopentadiene was used initially to demonstrate the concept and has been used as the benchmark reaction for mechanistic studies. Using the first generation of ligands, which contain separated DNA intercalation and metal binding moieties that are connected by a spacer, up to 50 % ee was found for this reaction (Scheme 17 a).…”

Synthesis and Evaluation of Biological Activities of Some 2-Hydroxy-1-Naphthyl Bicyclo [2.2.1] Heptene-2-Yl-Methanones

“…1,2,8,9 Rideout and Breslow 10 have studied the cycloaddition reaction of ethylenic ketones and cyclopentadiene in an aqueous medium and they reported the reaction rate is greater than 700 times faster than in non-aqueous media. Many catalysts such as Lewis acids, 5 Bronsted acids, 6,11 asymmetric helical polymers, 12 Cu 2+ ion-mediated nanotubes 13 and Micellar-DNAs 8, [13][14][15][16][17][18] have been employed for the Diels-Alder [4+2] cycloaddition reaction of cyclopentadiene (diene) and (E)-chalcones (dienophiles).…”

Aqueous phase fly-ash catalyzed [4+2] Diels-Alder reaction of aryl enones and cyclopentadiene: Synthesis and insect antifeedant activities of aryl bicyclo [2.2.1] heptene-2-yl-methanones

“…Reidant and Breslow [10] have investigated the aqueous phase reaction of cyclopentadiene and vinyl methyl ketones in water and the reaction rate is greater than 700 times faster than in organic solvents. Numerous catalysts including Lewis acids [5], Bronsted acids [5,11], Asymmetric catalyst with helical polymers [12], Cu 2+ ion-mediated nanotubes [13], DNA and Micellar based catalysts [7,14,15,16,17] have been employed for this [4+2] cycloaddition Diels-Alder reaction of cyclopentadiene(diene) and E-chalcones (dienophiles). The vinyl ketones, aza-vinyl ketones, bicyclo methanones possess antimicrobial activities and antibodies [18].…”