- NMR Spectroscopic Determination of the Solution Structure of a Branched Nucleic Acid from Residual Dipolar Couplings by Using Isotopically Labeled Nucleotides
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Only a small set of magnetic-field-induced residual dipolar couplings is required to determine the global structure of branched nucleic acids. This is demonstrated for the example of the Holliday junction (shown schematically) after 13C labelin
- Van Buuren, Bernd N. M.,Schleucher, Juergen,Wittmann, Valentin,Griesinger, Christian,Schwalbe, Harald,Wijmenga, Sybren S.
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p. 187 - 192
(2007/10/03)
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- Chemical synthesis of 13C labeled anti-HIV nucleosides as mass-internal standards
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Synthesis of [13C5]-labeled anti-HIV nucleosides, e.g. d4T, ddI, ddA, is described. The methodology used has been optimized due to the very high cost of the starting compound. The key step of this approach was the stereoselective dehomologation of 1,2:5,6-di-O-isopropylidene-3-oxo-α-D-glucofuranose (2) with periodic acid and sodium borohydride, which gave optically pure ribose derivative as the exclusive product. Nucleoside derivatives 6a-c were obtained from ribosylation of 5 with persilylated nucleobases under Vorbru?ggen conditions. Deoxygenation of 9a-c under Corey-Winter conditions afforded the desired labeled nucleoside analogues 12a-c.
- Saito, Yoshio,Zevaco, Thomas A,Agrofoglio, Luigi A
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p. 9593 - 9603
(2007/10/03)
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- A multigram, stereoselective synthesis of D-[13C5]ribose from D-[13C6]glucose and its conversion into [13C5]nucleosides
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The preparation of 13C-labeled ribonucleosides starting from D-[13D6]glucose in 45% overall yield is described. The key of this short synthetic way is the dehomologation of di-O-isopropylidene hexofuranose 2 with periodic acid and NaBH4 that afforded stereoselectively the labeled ribofuranose derivative 3 in high yield.
- Agrofoglio, Luigi A.,Jacquinet, Jean-Claude,Lancelot, Gerard
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p. 1411 - 1412
(2007/10/03)
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- Chemical Synthesis of 13C-labelled Monomers for the Solid-Phase and Template Controlled Enzymatic Synthesis of DNA and RNA Oligomers
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The preparation of 13C-labelled ribonucleosides starting from -glucose 1 and the corresponding nucleobases 5a-e or 6a-e (N6-benzoyl-adenine, N2-acetyl-guanine, N4-benzoyl-cytosine, uracil and thymine) in 47-66percent overall yield is described.Their subsequent transformation into 5'-O-dimethoxytrityl protected DNA-phosphoramidites and 5'-O-dimethoxytrityl-2'-O-trialkylsilyl protected RNA-phosphor-amidites for the solid phase synthesis of DNA- and RNA-oligomers and to 5'-O-ribo- and deoxyribo-nucleosidetriphosphates for template controlled enzymatic synthesis (polymerase- or reverse transcriptase reaction) has been carried out.
- Quant, S.,Wechselberger, R. W.,Wolter, M. A.,Woerner, K.-H.,Schell, P.,et al.
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p. 6649 - 6652
(2007/10/02)
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