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2'-OMe-5-Me-C (dmf) CE-Phosphoramidite

2'-OMe-5-Me-C (dmf) CE-Phosphoramidite

Phosphoramidite for the incorporation of a 2'-O-methyl 5-Me-ribo-C nucleobase within an oligonucleotide
  • High performance product for use on commercial oliognucleotide synthesizers.
  • Quality ensured by full QC testing.
  • Available packaged options for all common synthesizer instruments, and in bulk.
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Product information

Oligonucleotides containing 2'-OMe-5-Me-U (2'-OMe-T), 2'-OMe-N-Ac-5-Me-C or 2'-OMe-I are particularly applicable to triplex and antisense studies using 2'-OMe-RNA. For example, the immune stimulatory activity of CpG containing oligonucleotides in which C or G was substituted with 2'-OMe ribonucleotides, 5-Me-dC, or 2'-OMe-5-Me-C has been studied alone and in combination with TLR agonists. (1)
When 2'-OMe residues are incorporated into triplex forming oligonucleotides (2) (TFOs), similar trends in nuclease resistance and triplex stability are seen as with duplexes.
Hence they have been used to develop TFOs for use as gene targeting reagents.(3) Triplex stability can be increased further with the incorporation of 2'-OMe-5-Me-U residues into the oligonucleotide (4) using 2'-OMe-5-Me-U. Interestingly, 2'-OMe-5-Me C can have the opposite effect and destabilise the triplex, yet is still more stable than a DNA and/or RNA triplex. Incorporation of both 2'-OMe-5-Me U and 2'-OMe-5-Me C enables fine tuning of the Tm of the resulting triplex.

Ref:

  1. Modifications incorporated in CpG motifs of oligodeoxynucleotides lead to antagonist activity of toll-like receptors 7 and 9, D. Yu, D. Wang, F.-G. Zhu, L. Bhagat, M. Dai, E. R. Kandimalla and S. Agrawal, J. Med. Chem., 52, 5108-5114, 2009.
  2. Pyrimidine motif triplexes containing polypurine RNA or DNA with oligo 2'-O-Methyl or DNA triplex forming oligonucleotides, M. Behan and P.S. Miller, Biochim. Biophys. Acta., 1492, 155-162, 2000.
  3. The development of bioactive triple helix-forming oligonucleotides, M.M. Seidman, N. Puri, A. Majumdar, B. Cuenoud, P.S. Miller and R. Alam, in volume 1058, Therapeutic Oligonucleotides: Transcriptional and Translational Strategies for Silencing Gene Expression, 119–127, November 2005, Wiley-Blackwell.
  4. Effects of 5-methyl substitution in 2'-O-methyl oligo(pyrimidine)nucleotides on triple-helix formation, M. Shimizu, T. Koizumi., H. Inoue and E. Ohstuka, Bioorg. Med. Chem. Letts., 4, 1029-1032, 1994.
Brand BioAutomation
Base C
Modification 2'-OMe RNA
Sequence Internal

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