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Oligo Modifications List | Oligo Modifications Reference Category
Modification : dihydro dC (5-6 DHC)
Reference Catalog Number 26-6893
Category Minor Bases
Modification Code 5aza 5-6 DHC
5 Prime Y
3 Prime Y
Internal Y
Molecular Weight (mw) 292.18
Extinction Coeficient (ec) 7.4
Technical Info (pdf) PS26-6893.pdf
Catalog NoScalePrice
26-6893-0550 nmol$360.00
26-6893-02200 nmol$360.00
26-6893-011 umol$468.00
26-6893-032 umol$702.00
26-6893-1010 umol$3,744.00
26-6893-1515 umol$4,680.00

Discounts are available for dihydro dC (5-6 DHC)!
Modification* Discount Price Structure
1 site/order List price
2 sites/order 10% discount
3 sites/order 20% discount
4 sites/order 30% discount
5-9 sites/order 50% discount
10+ sites/order 60% discount
*Exceptions apply

Related Modifications
dihydro dU (5-6 DHdU)
dihydro dT (5-6 DHT)

5-aza, 5,6-dihydro dC (5,6-DHC) is primarily used to modify oligonucleotides slated for use as tools in cytosine-5-methyltransferase research studies. Cytosine-5-methyltransferases are key enzymes involved in methylation of CpG motifs necessary for epigenetic gene regulation in a wide variety of living organisms (1). Defects in the regulation of this set of enzymes are implicated in cancer (2). The reaction mechanism for these enzymes generates a transient dihydrocytosine as a key intermediate. In an oligo modified with 5-aza, 5,6-dihydro dC, the modification acts as a transition-state mimic, and binds non-covalently to the enzyme’s active site with high affinity. As such, it functions as a potent inhibitor of cytosine-5-methyltransferases, which makes them an excellent tool for structural studies, and an attractive alternative to 5-fluoro-cytosine (3).

References
1. Bestor, T., Laudano, A., Mattaliano, R., et al. Cloning and sequencing of a cDNA encoding DNA methyltransferase of mouse cells. The carboxyl-terminal domain of the mammalian enzymes is related to bacterial restriction methyltransferases. J. Mol. Biol. (1997), 270: 385-395.
2. Beaulieu, N., Morin, S., Chute, I.C., et al. An essential role for DNA methyltransferase DNMT3B in cancer cell survival. J. Biol. Chem. (2002), 277: 28176-28181.
Marquez, V.E., Goddard, A., Alvarez, E., et al. Oligonucleotides containing 5,6-dihydro-5-azacytosine at CpG sites can produce potent inhibition of DNA cytosine-C5-methyltransferase without covalently binding to the enzyme.Antisense & Nucleic Acid Drug Dev. (1999), 9: 415-421.
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