The synthesis of phosphoramidite reagents and solid-phase supports based on hydroxyprolinol for the introduction of the residues of biotin, lipoic acid, amino groups, and terminal acetylene groups at different positions of the oligonucleotide chain has been described. The efficiency of the reagents and supports has been confirmed by the synthesis of the corresponding modified oligonucleotides.

Synthesis of a phosphoramidite reagent for the preparation of oligonucleotides labeled at the 5′-end with a fluorescent dye, 3,3,3′,3′-tetramethyl-2,2′-indodicarbocyanine, is described. The efficiency of this reagent is confirmed by the synthesis of several labeled oligonucleotides.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

N-[2-(1-pyrenyl)ethyl]-1-pyrenylacetamide, bis[2-(1-pyrenyl)ethyl]amine, and N,N-bis[2-(1-pyrenyl)ethyl]succinamide were synthesized from 1-pyrenylacetic acid. These compounds contain adjacent pyrene residues and display excimer fluorescence. The latter compound, as a pentafluorophenyl ester, was used to prepare fluorescently labeled oligodeoxyribonucleotide (5)CAGGAAACAGCTATGAC. For N,N-bis[2-(1-pyrenyl)ethyl]succinamide, the excimer-to-monomer fluorescence ratio and intensity of fluorescence in water-methanol solutions changed in the presence of single-stranded and double-stranded oligonucleotides, upon attachment to an oligonucleotide, and upon hybridization of the resulting conjugate with the complementary nucleotide sequence.

Abstract A series of pyrene-containing reagents have been synthesized and used for the fluorescent labeling of oligonucleotides.

N-[2-(1-pyrenyl)ethyl]-1-pyrenylacetamide, bis[2-(1-pyrenyl)ethyl]amine, and N,N-bis[2-(1-pyrenyl)ethyl]succinamide were synthesized from 1-pyrenylacetic acid. These compounds contain adjacent pyrene residues and display excimer fluorescence. The latter compound, as a pentafluorophenyl ester, was used to prepare fluorescently labeled oligodeoxyribonucleotide (5)CAGGAAACAGCTATGAC. For N,N-bis[2-(1-pyrenyl)ethyl]succinamide, the excimer-to-monomer fluorescence ratio and intensity of fluorescence in water-methanol solutions changed in the presence of single-stranded and double-stranded oligonucleotides, upon attachment to an oligonucleotide, and upon hybridization of the resulting conjugate with the complementary nucleotide sequence.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Novel phosphoramidite reagents for nonradioactive polylabelling of oligonucleotides have been developed, including two branching reagents, 4 and 8, and a biotin-containing phosphoramidite 19 which call be used to incorporate a biotin moiety into any position of the oligonucleotide.

A novel phosphoramidite 4 based on the hydroxyprolinol 1 backbone has been synthesized and used to chemically prepare DNA fragments bearing a pyrene-containing nucleoside analogue.