5-aza-5,6-dihydro-dC-CE Phosphoramidite

default
10-1511
5'-Dimethoxytrityl-N4-dimethylformamidine-5,6-dihydro-5-aza-2'-deoxyCytidine,3'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite

Product Specifications

Formula:
C41H54N7O7P
M.W.:
787.89
F.W.:
292.18
Catalog Number: Select Pack Size and Format to Reveal

Description

Cytosine-5-methyltransferases are found in everything from archaebacteria to mammals and when the regulation of cytosine-5-methyltransferases goes awry, cancer can result. The mechanism of action for this family of enzymes involves attack of a cysteine thiol group on the C6 position of cytosine, leading to a transient dihydrocytosine intermediate, which then facilitates the nucleophilic attack by C5 on the activated methyl group of the S-adenosyl-L-methionine cofactor. As with many enzymes, the intermediate can be trapped using a suicide substrate and 5-fluoro-cytosine has been used extensively in this role. An alternate strategy is to use a transition-state mimic that binds to the active site with high affinity. An excellent candidate was found in 5-aza-5,6-dihydrocytosine. Despite not being covalently bound to the enzyme, it was found1,2 to be a more potent inhibitor of cytosine-5-methyltransferases than 5-fluoro-cytosine. 5-Aza-5,6-dihydro-dC is compatible with standard oligonucleotide synthesis and deprotection conditions and is an excellent tool for use in methyltransferase research.

Details

Usage

  • Coupling: No changes needed from standard method recommended by synthesizer manufacturer.
  • Deprotection: No changes needed from standard method recommended by synthesizer manufacturer.
Specifications
Diluent Anhydrous Acetonitrile
Storage Freezer storage, -10 to -30°C, dry
Stability 2-3 days


Dilution/Coupling Data

The table below show pack size data and, for solutions, dilution and approximate coupling based on normal priming procedures.

ABI 392/394

Catalog # Pack Size Grams/Pack 0.1M Dil. (mL) Approximate Number of Additions
LV40 LV200 40nm 0.2μm 1μm 10μm
10-1511-02 0.25 g .25grams 3.17 92.33 55.4 34.63 25.18 18.47 4.62
10-1511-90 100 µmol .079grams 1 20 12 7.5 5.45 4 1
10-1511-95 50 µmol .039grams 0.5 3.33 2 1.25 0.91 0.67 0.17

Expedite

Catalog # Pack Size Grams/Pack Dilution (mL) Approximate Number of Additions
Molarity 50nm 0.2μm 1μm 15μm
10-1511-02 0.25 g .25grams 4.74 0.07 88.4 55.25 40.18 5.53
10-1511-90 100 µmol .079grams 1.5 0.07 23.6 14.75 10.73 1.48
10-1511-95 50 µmol .039grams 0.75 0.07 8.6 5.38 3.91 0.54