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Oligo Synthesis

Oligo Synthesis : CEPs

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  • Catalogue
  • Description
  • Protocols
  • References
  • Applications & Benefits

5-Carboxy-dC-CE Phosphoramidite

5-Carboxy-dC-CE Phosphoramidite

Glen Research

Catalogue No.DescriptionPack SizePriceQty
  • Change to:
  • €
10-1066-025-Carboxy-dC-CE Phosphoramidite0.25g£960.00£912.00Offer until : 31-Mar-2021Offer Code : GLEN55% off all Glen productsView OfferQuantityAdd to Order
10-1066-905-Carboxy-dC-CE Phosphoramidite100umole£360.00£342.00Offer until : 31-Mar-2021Offer Code : GLEN55% off all Glen productsView OfferQuantityAdd to Order
10-1066-955-Carboxy-dC-CE Phosphoramidite50umole£184.00£174.80Offer until : 31-Mar-2021Offer Code : GLEN55% off all Glen productsView OfferQuantityAdd to Order

5-Carboxy-dC-CE Phosphoramidite

5-Carboxy-dC-CE Phosphoramidite

Glen Research

Structure

Catalog Number: 10-1066-xx

Description: 5-Carboxy-dC-CE Phosphoramidite

5"-Dimethoxytrityl-N-benzoyl-5-ethylcarboxy-2"-deoxyCytidine,3"-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite
Formula: C49H56N5O10PM.W.: 905.97F.W.: 333.19

Diluent: Anhydrous Acetonitrile
Coupling: No changes needed from standard method recommended by synthesizer manufacturer.
Deprotection: Cleavage and deprotection should be carried out using a mild deprotection: 0.4M methanolic sodium hydroxide (methanol:water 4:1) for 17 hours at room temperature. Pipet off support and neutralize with 2M TEAA.Note: NaOH is not compatible with dmf protecting groups.
Storage: Refrigerated storage, maximum of 2-8°C, dry

Stability in Solution: 2-3 days

DNA Methylation

One of the fastest growing fields in biology and cancer research isepigenetics. While the underlying genetic code defines which proteins and geneproducts are synthesized, it is epigenetic control that defines when and wherethey are expressed. This dynamic control of gene expression is essential for Xchromosome inactivation, embryogenesis, cellular differentiation and appearsintegral to memory formation and synaptic plasticity.

In 2009, two reports1,2 described the discovery of5-hydroxymethyl-2’-deoxyCytidine (hmdC), a novel dC modification in Purkinjeneurons and embryonic stem cells. Later, a third report found this modificationto be strongly enriched in brain tissues associated with higher cognitivefunctions.3 This new dC modification is generated by the action ofa-ketoglutarate dependent TET enzymes (ten eleven translocation), which oxidizes5-Me-dC to hmdC. This finding stimulated discussion about active demethylationpathways that could occur, e.g., via base excision repair (BER), with the helpof specialized DNA glycosylases. Alternatively, one could envision a process inwhich the hydroxymethyl group of hmdC is further oxidized to 5-formyl-dC (fdC)or 5-carboxy-dC (cdC) followed by elimination of either formic acid or carbondioxide4,5.

Glen Research has supported this research since its inception by providingthe building blocks for the synthesis of oligonucleotides containing all the newdC derivatives - hmdC, fdC and cdC. The first generation hmdC phosphoramiditewas fairly very well accepted but requires fairly harsh deprotection conditions.Therefore, a second generation building block (5-Hydroxymethyl-dC II) developedby Carell and co-workers that is compatible with UltraMild deprotection has beenintroduced.6 A second generation fdC-phosphoramidite (5-Formyl-dCII), also developed by Carell and co-workers, has been introduced since it doesnot require the post synthesis elimination step of the first generationversion.7

5-Formyl-dC and 5-carboxy-dC may find uses in research into DNA damage andrepair processes.

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5-Carboxy-dC-CE Phosphoramidite

5-Carboxy-dC-CE Phosphoramidite

Glen Research

MSDS

Glen Report 23.1

Glen Report 23.2

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5-Carboxy-dC-CE Phosphoramidite

5-Carboxy-dC-CE Phosphoramidite

Glen Research

  1. S Kriaucionis and N Heintz, Science, 2009, 324, 929-30
  2. D Globisch, et al., PLoS One, 2010, 5, e15367
  3. S G Jin, X Wu, A X Li and G P Pfeifer, Nucleic Acides Res., 2011
  4. K M Schmitz, et al., Mol Cell, 2009, 33, 344-53
  5. S C Wu and Y Zhang, Nat Rev Mol Cell Biol, 11, 607-20
  6. M Sumino, A Ohkubo, H Taguchi, K Seio and M Sekine, Bioorganic & Medicinal Chemistry Letters, 2008, 18, 274-277
  7. N Karino, Y Ueno andA Matsuda, Nucleic Acids Res., 2001, 29, 2456-2463

If you cannot find the answer to your problem below then please contact us or telephone 01954 210 200

5-Carboxy-dC-CE Phosphoramidite

5-Carboxy-dC-CE Phosphoramidite

Glen Research

DILUTION/COUPLING DATA

The table below shows pack size data and, for solutions, dilutions and approximate couplings based on normal priming procedures.

ABI 392/394
Cat.No.PackSizeGrams/Pack0.1M Dil.(mL)LV40LV20040nm0.2µm1µm10µm
Approximate Number of Additions
10-1066-020.25grams.25grams2.7678.6747.229.521.4515.733.93
10-1066-90100µmoles.091grams120127.55.4541
10-1066-9550µmoles.045grams.53.3321.25.91.67.17
Expedite
Cat.No.PackSizeGrams/PackDilution(mL)Molarity50nm0.2µm1µm15µm
Approximate Number of Additions
10-1066-020.25grams.25grams4.12.077647.534.554.75
10-1066-90100µmoles.091grams1.5.0723.614.7510.731.48
10-1066-9550µmoles.045grams.75.078.65.383.91.54
Beckman
Cat.No.PackSizeGrams/PackDilution(mL)Molarity30nm200nm1000nm
Approximate Number of Additions
10-1066-020.25grams.25grams4.12.0777.648.535.27
10-1066-90100µmoles.091grams1.5.0725.215.7511.45
10-1066-9550µmoles.045grams.75.0710.26.384.64

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