7-Deaza-2′-deoxyguanosines Functionalized with 7-(ω-Aminoalk-1-YNYL) Residues

Ramzaeva, N.; Mittelbach, Cathrin; Seela, Frank

doi:10.1080/07328319908044747

Cited by 9 publications

(4 citation statements)

References 3 publications

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“…The β-cyanoethyl phosphoramidites containing phthaloyl-protected propargylamine side chains (2)(3)(4)(5) were incorporated at the penultimate position of the 3 -end of the primer using phosphorothioate chemistry. To obtain coupling yields of the modified building blocks greater than 96%, we have increased the coupling step by a factor of 10.…”

Section: Resultsmentioning

confidence: 99%

Novel Propargylamine-Linked Nucleosides for High Throughput SNP Genotyping by Maldi-Tof MS

Wenzel¹,

Fröhlich²,

Strassburger³

et al. 2001

Nucleosides, Nucleotides and Nucleic Acids

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The synthesis of positively charged and mass tagged nucleosides containing a quaternary ammonium functionality within the penultimate position of a primer is described. Neutralization of the sugar/thiophosphate backbone by alkylation increases the detection sensitivity in the mass spectrometric analysis by a factor of at least 100. The variable introduction of these novel compounds within the extension primers enables flexible design of multiplex genotyping reactions.

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Section: Resultsmentioning

confidence: 99%

Novel Propargylamine-Linked Nucleosides for High Throughput SNP Genotyping by Maldi-Tof MS

Wenzel¹,

Fröhlich²,

Strassburger³

et al. 2001

Nucleosides, Nucleotides and Nucleic Acids

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“…The key intermediate for the synthesis of the title compounds is the 7-iodo nucleoside 2b (Chart 1)which has been described earlier (Ramzaeva and . Pd(0)-catalyzed cross coupling reaction of compound 2b with 3-phthalimido-1-propyne (3a) (Gibson and Benkovic, 1987) gave 4a in 80% yield (Ramzaeva et al, 1999;. Analogously, compound 2b was now reacted with 4-phthalimido-1butyne (3b) (Meyer, 1994) to give 4b in about the same yield.…”

Section: Synthesis Of Monomersmentioning

confidence: 99%

“…Subsequently, both compounds were treated with 4,4′dimethoxytriphenyl-methyl chloride (Schaller et al, 1963) in pyridine to give the 5′-protected derivatives 6a (86%) and 6b (65%), respectively (Chart 2). The dimethoxytrityl derivative 6a was phosphitylated with 2-cyanoethyl diisopropylphosphoramidochloridite (Beaucage and Caruthers, 1981) following a standard protocol to yield the phosphoramidite 7a (Ramzaeva et al, 1999 Characterization of the Monomers. The newly synthesized derivatives (Charts 1 and 2) were characterized by elemental analysis as well as by 1 H, 13 C, and 31 P NMR spectroscopy (Tables 1, 2, and Experimental Procedures).…”

Section: Synthesis Of Monomersmentioning

confidence: 99%

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Oligonucleotides Incorporating 7-(Aminoalkynyl)-7-deaza-2‘-deoxyguanosines: Duplex Stability and Phosphodiester Hydrolysis by Exonucleases

et al. 2002

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Oligonucleotides containing 7-(omega-aminoalkyn-1-yl)-7-deaza-2'-deoxyguanosines (1a-c) were investigated regarding their thermal stability (T(m) values) as well as their phosphodiester hydrolysis catalyzed by exonucleases. Those derivatives are suitable for the labeling of nucleic acid constituents as well as for the postlabeling of DNA. For this, the phosphoramidites 7a,c (obtained from the nucleoside 1a,b), protected by an isobutyryl group at the 2-amino group and a phthaloyl residue at the side-chain amino function, were synthesized. Using compounds 7a,c together with the phosphoramidite of 1c in solid-phase synthesis, a series of self-complementary and non-self-complementary oligonucleotides were prepared and characterized by MALDI-TOF mass spectrometry. A comparison of the T(m) values of the modified oligomers shows that the thermal stability of the duplexes decreases with the length of the nucleobase 7-(omega-aminoalkyn-1-yl) side chain. Exonucleolytic cleavage of oligonucleotide single strands incorporating either the 7-(3-aminopropyn-1-yl)- or the 7-(4-aminobutyn-1-yl)-substituted nucleosides 1a or 1b, respectively, reveals that 3' --> 5' specific snake venom phosphodiesterase liberates 1a 5'-monophosphate but not the methylene-extended 1b 5'-monophosphate. On the contrary, the 5' --> 3' specific bovine spleen exonuclease is able to cleave off single 1a and 1b 3'-monophosphate residues; its action is, however, terminated in the case of oligonucleotides containing two consecutive 1a or 1b nucleotide units.

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