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Oligo Synthesis

Oligo Synthesis : CEPs

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Ara-C-CE Phosphoramidite

Ara-C-CE Phosphoramidite

Glen Research

Description

Ara-C-CE Phosphoramidite

Structure

Catalog Number: 10-4010-xx

Description: Ara-C-CE Phosphoramidite

5'-Dimethoxytrityl-N-acetyl-2'-O-acetyl-Cytidine Arabinoside,
3'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite
Formula: C43H52N5O10P M.W.: 829.87 F.W.: 305.18

Diluent: Anhydrous Acetonitrile
Coupling: No changes needed from standard method recommended by synthesizer manufacturer.
Deprotection: No changes needed from standard method recommended by synthesizer manufacturer.
Storage: Freezer storage, -10 to -30°C, dry
Stability in Solution: 24 hours

THERAPEUTIC Nucleosides

Cytosine Arabanoside (Ara-C) is an anti-viral drug which has achieved limited use. Its effect on DNA structure and activity can be investigated by incorporating it into synthetic oligonucleotides.

Zebularine (pyrimidin-2-one ribonucleoside) is a cytidine analogue that acts as a DNA demethylase inhibitor, as well as a cytidine deaminase inhibitor. This structure is very active biologically and Zebularine is now used as a potent anti-cancer drug. A 2’-deoxynucleoside analogue of Zebularine, 5-methyl-pyrimidin-2-one, 2’-deoxynucleoside, has been used to probe the initiation of the cellular DNA repair process by making use of its mildly fluorescent properties. This combination of biological activity and fluorescence properties would make 5-Me-2'-deoxyZebularine a strong addition to our array of nucleoside analogues.

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.

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Protocols

MSDS

 

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Applications & Benefits

DILUTION/COUPLING DATA

The table below shows pack size data and, for solutions, dilutions and approximate couplings based on normal priming procedures. Please link for more detailed usage information with the various synthesizers.

ABI 392/394
Cat.No. Pack
Size
Grams/
Pack
0.1M Dil.
(mL)
LV40 LV200 40nm 0.2µm 1µm 10µm
Approximate Number of Additions
10-4010-02 0.25grams .25grams 3.01 87 52.2 32.63 23.73 17.4 4.35
10-4010-90 100µmoles .083grams 1 20 12 7.5 5.45 4 1
Expedite
Cat.No. Pack
Size
Grams/
Pack
Dilution
(mL)
Molarity 50nm 0.2µm 1µm 15µm  
Approximate Number of Additions
10-4010-02 0.25grams .25grams 4.5 .07 83.6 52.25 38 5.23  
10-4010-90 100µmoles .083grams 1.5 .07 23.6 14.75 10.73 1.48  
Beckman
Cat.No. Pack
Size
Grams/
Pack
Dilution
(mL)
Molarity 30nm 200nm 1000nm    
Approximate Number of Additions
10-4010-02 0.25grams .25grams 4.5 .07 85.2 53.25 38.73    
10-4010-90 100µmoles .083grams 1.5 .07 25.2 15.75 11.45    

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Related products

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