Functionalisation of a diene-modified hairpin mimic via the Diels–Alder reaction

Abstract

A highly stable 1,3-butadiene-derived DNA hairpin mimic and its derivatisation via the Diels-Alder reaction with various dienophiles are described.

Diels–Alder “click” reactions: recent applications in polymer and material science

“…For example, a number of studies described the use of DA ''click'' chemistry with oligonucleotides 167 bearing a diene or dienophile moiety with small molecules (carboxylic acid, activated ester, benzophenone, pyrene, fluorescent dye, TEMPO, biotin, etc. ), [168][169][170][171][172][173][174][175][176][177][178][179][180] polymers, 170,171,181 gold nanoparticles, 171,182 and glass surfaces. [183][184][185][186][187] The reactions were carried out without interference of the many functional groups presented in RNA and DNA.…”

High definition polyphosphoesters: between nucleic acids and plastics

“…30,31 Häner has used a linear diene to generate hairpins capable of participating in Diels-Alder reactions, permitting conjugation of heterospecies to the nucleic acids via maleimides. 32 Alternatively, if placed at both ends of a hairpin, spacers furnish a way to make compact cyclic DNAs. This was first performed using 2 x C3 units to create 'sausage DNA' which showed a Tm 40 °C higher than the uncapped version.…”

Novel strategies for the site-specific covalent labelling of nucleic acids

“…Tona and Haner developed a 4 base hairpin mimic containing a 1,3-butadien building block which builds a stable hairpin. 79 Conjugation using diff~rent maleinimides within seven days at 20 QC resulted in complete conversion retaining the DNA hairpin structure. Later on crosslinking of complementary strands could be achieved using a bismaleinimide and this butadiene building block.…”