Abstract
The polycondensation of a silane derivative such as aminopropyltrimethoxysilane (ATMS) in the presence of nucleic acids has never been investigated. Our group has previously demonstrated that in chloroform ATMS hydrolysis and polycondensation were faster when the reaction were carried out in the presence of double stranded DNA (146 bp). The results showed that the kinetics of ATMS hydrolysis was affected by the base type used, a fast hydrolysis reaction rate being observed with nucleotide molecules containing adenosine group, and that in the absence of water the amino group of deoxyadenosine units, and not the hydroxylic group of the sucrose residue, can react with ATMS methoxy groups. The present work was initiated aiming at providing a better understanding of this effect. It was observed that the polymerization degree of oligodeoxyadenylate has a clear impact on the kinetic of reaction this effect being as much important as the polymerization degree of the oligodeoxyadenylate was high. Structural investigation by molecular modeling showed that this enhanced reactivity can be explained by conformational effects. Altogether, these results are accounted for assuming that DNA can act as a specific template for ATMS polycondensation, in organic medium such as chloroform, opening the way to possible DNA encapsulation, and a new way for DNA chemical modification in organic solvent.
Highlights
Oligonucleotides have been seldom investigated as catalyst for simple organic reaction [1], but rather as catalyst for biological systems (RNA and DNA ligation, hydrolytic cleavages, photorepair of DNA, reactions of peptides...) [2]
3 Results and discussion 3.1 Enhancement of ATMS reaction in chloroform by various oligonucleotides In order to confirm the impact of the nucleotide type on the methanol production reaction rate in the ATMS-DNA system, experiments were carried out using homo-oligonucleotides composed of 20 residues of deoxyadenosine, deoxycytidine, deoxyguanosine or deoxythymidine
It was observed that 3h after ATMS addition, the methanol formation reaction was complete in the presence of oligo-dA20 whereas with the other homo-oligonucleotides, reaction reached 55%
Summary
Oligonucleotides have been seldom investigated as catalyst for simple organic reaction [1], but rather as catalyst for biological systems (RNA and DNA ligation, hydrolytic cleavages, photorepair of DNA, reactions of peptides...) [2]. DNA synthesis has been mostly studied in the case of biological processes applied to nucleic acid templated synthesis such as replication of genetic information, or transcription of DNA into RNA [3,4,5]. The hydrolysis and the step polymerization of ATMS have been investigated by 1H and 29Si NMR in the presence and the absence of ds-DNA in chloroform. The ATMS reaction was studied in presence of different DNA bases, nucleosides and nucleotides in order to clarify the influence of the nucleic acid structure. The reaction of ATMS in the presence of DNA was explained by its reactivity with deoxyadenosine units. This unexpected reactivity of adenine based units deserves a specific investigation, and the presentpaper reports efforts to address such templated mechanism
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