Modification of Oligo (Poly) Nucleotide Phosphomonoester Groups in Aqueous Solutions

DNA duplex and dumbbells containing chemically active acylphosphate internucleotide groups were synthesized. To obtain these compounds the chemical ligation method was used. The acylphosphate group was inserted into a DNA duplex and dumbbells as a result of template-directed condensation of 5P-phosphate and especially introduced 3P-carboxy groups of oligonucleotides. 1-Ethyl-3-(3P-dimethylaminopropyl)carbodiimide (EDC) was used as a condensing agent. Oligonucleotides containing a carboxy group were obtained by the interaction of their 3P-phosphate with glycine methyl ester under the action of EDC, followed by ester hydrolysis. The yields of acylphosphatecontaining double-stranded oligonucleotides achieved 15^25% depending on the structure of their precursors. It was shown that these compounds are acylating agents and are efficiently cleaved in near-physiological conditions under the action of ethylenediamine or N-methylimidazole. These results indicate that doublestranded oligonucleotides carrying acylphosphate internucleotide groups could constitute new crosslinking reagents for affinity modification of DNA recognizing proteins.z 1998 Federation of European Biochemical Societies.

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“…This reaction was carried out with a quantitative yield. It is in agreement with data obtained earlier [15].…”

Section: Resultssupporting

confidence: 94%

Design and synthesis of double‐stranded oligonucleotides containing reactive acylphosphate internucleotide groups

1998

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“…[6] However, this approach to derivatization excludes the use of fluorescence markers or buffer systems with carboxylic acid, primary amino, or phosphate groups. It involves the hydrolysis of DNA, fluorescence labeling of modified and unmodified nucleotides, micellar electrokinetic chromatography, and laser-induced-fluorescence detection (CE-LIF) with 4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diazas-indacene-3-propionylethylenediamine (BODIPY FL EDA) as the fluorescence marker.…”

mentioning

confidence: 99%

Capillary Electrophoresis Analysis of DNA Adducts as Biomarkers for Carcinogenesis

et al. 2004

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“…With this method the positively charged fluorescence marker and degradation product of EDC (for structure see Fig. 1, [18]) are complexed by the tetraphenyl borate anion and removed from solution. To prevent the inclusion of the derivatised nucleotides in the voluminous precipitate, in a following step the tetraphenyl borate complex was diluted in methylene chloride.…”

Section: Resultsmentioning

confidence: 99%

Determination of the DNA methylation level of the marbled crayfish: An increase in sample throughput by an optimised sample preparation

Schiewek¹,

Wirtz²,

Thiemann³

et al. 2007

Journal of Chromatography B

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Modification of Oligo (Poly) Nucleotide Phosphomonoester Groups in Aqueous Solutions

Cited by 44 publications

References 16 publications

Design and synthesis of double‐stranded oligonucleotides containing reactive acylphosphate internucleotide groups

Design and synthesis of double‐stranded oligonucleotides containing reactive acylphosphate internucleotide groups

Capillary Electrophoresis Analysis of DNA Adducts as Biomarkers for Carcinogenesis

Determination of the DNA methylation level of the marbled crayfish: An increase in sample throughput by an optimised sample preparation

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