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- W2040835372 abstract "Syntheses via the phosphotriester method are described for DNA oligonucleotides containing O4-ethylated thymine (e 4 Thy) and adenine (Ade) bases, d(e 4 TpA), d(Ape 4 T), and d(Ape 4 TpA), for their unmodified analogs, d(TpA), d(ApT), and d(ApTpA), and for d(Tpe 4 TpT). 1 H NMR chemical shift data obtained from 10 to 70 °C at 300 and 500 MHz show that these molecules form right-handed minihelices at low temperature in aqueous solution; the presence of the O4-ethyl group does not seem to have a drastic effect on the stacking geometry of the thymine base. The presence of right-handed stacking is confirmed by circular dichroic data obtained over a similar temperature range. Coupling constants for the sugar ring indicate that the e 4 Tp unit of d(e 4 TpA) does not show the shift towards the 3′-endo (N) pucker noted for the corresponding unit of d(e 4 TpT). A prominent quasimolecular ion peak [M – H] − is observed for the modified and unmodified molecules in the spectra obtained by Fast Atom Bombardment mass spectrometry (FAB-MS) operating in the negative ion mode, indicating that the labile O4-ethyl group is sufficiently stable to withstand the ionization process used in this method. In addition, a number of fragment ion peaks such as [O4-ethylthymine – H] − are observed that reveal the potential of FAB-MS for characterizing DNA oligomers modified by alkylating agents. Keywords: oligonucleotides, O-alkylation, stereochemistry, NMR, mass spectrometry." @default.
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- W2040835372 date "1990-11-01" @default.
- W2040835372 modified "2023-10-18" @default.
- W2040835372 title "Synthesis and properties of DNA oligomers containing an O4-ethylated thymine. d(e4TpA), d(Ape4T), d(Ape4TpA), and d(Tpe4TpT)" @default.
- W2040835372 doi "https://doi.org/10.1139/v90-308" @default.
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