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  6. dC (Ac) Me-Phosphoramidite

dC (Ac) Me-Phosphoramidite

dC (Ac) Me-Phosphoramidite

dC (Ac) Me-Phosphoramidite

CAS No.:833480-37-8

Phosphoramidite used to incorporate a deoxycytidine into an oligonucleotide, with a methylated backbone.

Key features

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  • Useful for creating nuclease resistant methyl phosphotriester linkage.
  • Applications in nucleic acid therapeutics.
  • Compatible with UltraMILD synthesis.
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Product information

The UltraMILD set of methyl phosphoramidites, in conjunction with UltraMILD deprotection conditions, can be used to prepare the interesting, nuclease resistant methyl phosphotriester linkage. These have potential therapeutic applications.

We also produce a range of ethyl phosphoramidites with classical nucleobase protection. Nuclease resistant P-ethoxy oligonucleotides (a hydrophobic analogue of phosphodiesters) have been shown, through incorporation into liposomes, to be effective in the inhibition of protein expression and cell growth in therapeutic applications.(1) The neutral charge and slight lipophilic character appears to improve the delivery of the oligonucleotide into a cell.

Ref:

  1. (a) Cellular pharmacology of P-ethoxy antisense oligonucleotides targeted to Bcl-2 in a follicular lymphoma cell line, Y. Gutiérrez-Puente, A.M. Tari, R.J. Ford, R. Tamez-Guerra, R. Mercado-Hernandez, M. Santoyo-Stephano, and G. Lopez-Berestein, Leuk. Lymphoma., 44, 1979-85, 2003. (b) Safety, pharmacokinetics, and tissue distribution of liposomal P-ethoxy antisense oligonucleotides targeted to Bcl-2, Y. Gutiérrez-Puente, A.M. Tari, C. Stephens, M. Rosenblum, R.T. Guerra, G. Lopez-Berestein, J. Pharmacol. Exp. Ther., 291, 865-9, 1999.

Applicable Products

LK2050 Ac-dC-Me Phosphoramidite
LK2051 iPr-Pac-dG-Me Phosphoramidite
LK2052 Pac-dA-Me Phosphoramidite
LK2078 dT-Me Phosphoramidite

Physical & Dilution Data

Unit weights are expressed for the methyl triester form. Dilution volumes (in ml) are for 0.1M solutions in dry acetonitrile (LK4050) Adjust accordingly for other concentrations. For µmol pack sizes, products should be diluted as 100µmol/ml to achieve 0.1M, regardless of molecular weight.

Item

Mol. Formula

Mol. Wt.

Unit Wt.

250mg

500mg

1g
LK2050 C39H49N4O8P 732.81 303.21 3.41 6.82 13.65
LK2051 C49H59N6O9P 907.21 343.23 2.76 5.51 11.03
LK2052 C46H53N6O8P 848.93 327.23 2.94 5.89 11.78
LK2078 C38H48N3O8P 705.79 318.22 3.54 7.08 14.17

Coupling

No changes are required from the standard method recommended by the synthesiser manufacturer. Coupling is as per standard nucleoside amidites. If the oligo contains many dG residues, use phenoxyacetic anhydride in the Cap Mix A (LK4210) to avoid the exchange of the iPr-Pac group on the dG with acetate from the acetic anhydride capping mix.

Deprotection

Use UltraMILD deprotection with 0.05M potassium carbonate in methanol to leave the methyl triester intact.1

Storage & Stability

Refrigerate the solids at a maximum of 2-8°C. Stability in solution is 2-3 days.

Reference

  1. See also: T. Atkinson and M. Smith in Oligonucleotide synthesis: a Practical Approach, M.J. Gait (editor), IRL Press Limited, Oxford, 1984, pages 68-70.

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