We enable nucleic acid labeling bioconjugation
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5-Hydroxymethyl-dC CEP

Amidite for the Study of Epigenetics

Currency:  
  • Size
  • Catalog No.
  • Price
  • 50 µmol (39.29 mg)
  • BCA-26-50

  • € 300,00
  • 100 µmol (78.58 mg)
  • BCA-26-100

  • € 520,00
  • 250 mg
  • BCA-26-250

  • € 1.000,00
Clear
  • Base modifications, especially 5-methyl deoxycytidine (5-mdC) play a crucial role in the silencing of genes. More recently, it has been discovered that oxidized variants of 5-mdC could have a biological function in the reactivation process of silenced genes.
    A major hypothesis has proposed eradication of 5-mdC through stepwise oxidation by Tet enzymes and decarboxylation to yield the “active” dC.
    5-Hydroxymethyl cytidine (5-hmdC) is the first oxidized variant of 5-mdC and was found to be semi-permenant nucleoside in the cortex of vertebrates. In order to study distinct sequences containing 5-hmdC modifications it is necessary to synthesize oligonucleotides by solid-phase synthesis. Our 5-hydroxymethyl cytidine CEP is the ideal building block to generate 5-hmdC modified oligonucleotides.

    LITERATURE

    S Kriaucionis N Heintz, N. Science, 2009, 423, 929-930.

    M Tahiiliani, K. P. Koh, Y. H. Shen, W. A. Pastor, H. Badukwala, Y. Brundo, S. Agrawal, I. M. Iyer, D. R. Liu, A. Rao, Science, 2009, 324, 930-935

    M. Munzel, D. Globisch, T. Bruckl, M. Wagner, V. Welzmiller, S. Michelakis, M. Müller, M. Biel, T. Carell, Angew. Chemie – Int. Ed. 2010, 49, 5375-5377

    A. Szwagierczak, S. Bultmann, C. S. Schmidt, F. Spada, H. Leonhardt, Nucleic Acids Res. 2010, 38, e181

    M. Munzel, D. Globisch, C. Trindler, T. Carell, T., Org. Lett 2010, 12(24), 5671-5673

    • Molecular Formula

      C41H48N5O9P

    • Shelf Life

      12 months unopened after receipt

    • Storage Conditions

      -20°C dry, inert gas

    • Molecular Weight

      785.83 g/mol

    • Purity

      ≥ 90% (31P NMR)

    • Physical State

      white to yellow colored fluffy solid

    • CAS Number

      1257247-42-9

    • Additional name

      5-Hydroxymethyl-deoxycytidine-CEP (5-HmdC CEP)

    • Preparation/Handling

      Solid-Phase Synthesis Information:
      Note: The deprotection method required for this phosporamidite is not compatible with dmf protecting groups (e.g. dmf-dG CEP). Please adjust the “standard” phosphoramidites for solid-phase synthesis before starting the synthesis, if necessary.
      Diluent: Anhydrous acetonitrile (0.1 M final concentration is recommended)
      Coupling: Standard protocol as recommended by synthesizer manufacturer.
      Deprotection: 0.4 M NaOH in MeOH/H2O (4:1, v/v) for 17 h at room temperature (standard phosphoramidites without dmf protecting group). Alternatively, 50 mM K2CO3 in MeOH for 4 h at room temperature (ultramild phosphoramidites needed).
      Stability in Solution: Maximum of 2-3 days