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Quadruplex and Pentaplex Self-Assemblies of Oligonucleotides Containing Short Runs of 8-aza-7-deaza-2'-deoxyisoguanosine or 2'-deoxyisoguanosine

Quadruplex and Pentaplex Self-Assemblies of Oligonucleotides Containing Short Runs of 8-aza-7-deaza-2'-deoxyisoguanosine or 2'-deoxyisoguanosine

F Seela, R Kröschel

Bioconjug Chem. Nov-Dec 2001;12(6):1043-50.

PMID: 11716698

Abstract:

Oligonucleotides containing 8-aza-7-deaza-2'-deoxyisoguanosine (4) were investigated regarding their self-assembly in aqueous solution. The aggregation of 4 was compared with that of oligonucleotides containing 2'-deoxyisoguanosine (2b) and 2'-deoxyguanosine (1b). For this purpose the phosphoramidite of 4 was synthesized which was protected by a dibutylaminomethylidene residue at the amino group and a diphenylcarbamoyl residue at the 2-oxo function. Solid-phase synthesis furnished oligonucleotide containing short runs of the nucleoside 4. The self-assembly of the oligonucleotide 5'-d(T(4)4(4)T2) was studied by ion-exchange chromatography. The formation of a pentaplex was observed in the presence of Cs+, while a tetraplex is formed when the counter ion is Na+ or Rb+. The cation selectivity of the oligonucleotide 5'-d(T(4)4(4)T2) was found to be different from the parent 5'-d(T(4)isoG(4)T2) which was forming the tetraplex as well as a pentaplex in aq RbCl solution.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
IAR42411326	DMT-2′O-TBDMS-rU-6-13C,5-d phosphoramidite			Price

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