F. Morvan

Oligonucleotide Carbohydrate-Centered Galactosyl Cluster Conjugates Synthesized by Click and Phosphoramidite Chemistries

Oligonucleotide glycoconjugates with a mannose or galactose core bearing four galactose residues introduced by phosphoramidite chemistry and copper catalyzed azide alkyne 1,3-dipolar cycloaddition (click chemistry) have been synthesized. A first click reaction allowed the introduction on a solid support of a mannose core on which four pentynyl linkers were introduced using a phosphoramidite derivative. After the elongation of the oligonucleotide, a second click reaction performed either on solid support or in solution allowed the introduction of four galactose azide derivatives. Repeating the phosphoramidite and click chemistries afforded an oligonucleotide glycoconjugate dendrimer bearing 16 galactoses on its periphery.

Combinatorial and Automated Synthesis of Phosphodiester Galactosyl Cluster on Solid Support by Click Chemistry Assisted by Microwaves

Small libraries of di-, tri-, and tetragalactosyl clusters were efficiently synthesized using combinatorial methodology, on solid support, by click chemistry assisted by microwaves, starting from different poly alkyne DNA-based scaffolds and two galactosyl azide derivatives. The scaffold was synthesized by standard DNA solid-supported phosphoramidite chemistry using a novel alkyne phosphoramidite and an alkyne solid support. The proportion of each glycocluster in a library was modulated using different molar ratios of both galactose azides.

Direct MALDI-TOF MS analysis of oligonucleotides on solid support through a photolabile linker.

MALDI-TOF mass spectrometry was used to analyze oligonucleotides still anchored to long-chain alkylamine controlled-pore glass (LCAA-CPG) through a photolabile linker. This technique is useful to follow supported chemical reactions in real time and monitor by-products formation.

Synthesis of oligonucleotide prodrugs bearing N-acetyl nucleobases.

Abstract N-Acetyl oligonucleotides and their prodrugs were synthesized on photolabile solid support. Tm studies showed a decrease of hydridization for N-acetyl A and G and an increase for N-acetyl C. In cells extract, acetyl groups were hydrolysed.

SELF-ASSEMBLY ARCHITECTURES OF NEW DNA-BASED STRUCTURES IN AIR AND IN LIQUIDS ANALYZED BY ATOMIC FORCE MICROSCOPY

The architecture of self assembled X shaped DNA structure was studied by AFM on mica. The dimensions and extent of self assembled structures were influenced by mica surface treatment and depended on whether observations were performed in air or in Tris buffer solution. A molecular model is proposed.

The Pro-Oligonucleotide Approach: Chimeric Dodecamers Bearing Six Bioreversible Protecting Groups

Abstract Chimeric dodecamers prooligo bearing a 6 POM gap were fblly hydrolyzed in total CEM cell extract with half-lives of about 30 h.

Triplex Formation of α-Oligodeoxynucleotides Containing 5-Me-α-dC(N-4-Spermine)

Abstract Pyrimidine α-ODNs containing 5-Me-α-dC(N-4-spermine) at the 5′-end or in the sequence were synthesized. The corresponding αββ triple helices were strongly stabilized by Mg2+ cations. Unlike in β-series these triplexes were not stabilized at pH 7.