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Published TCIMAIL newest issue No.198
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Easy-to-Handle and Safe Phosphitylation Reagent for Syntheses of DNA and RNA Fragments
No.145(March 2012)
Protected 2’-deoxyribo and ribonucleoside-3’-phosphoramidites, which have been widely used for syntheses of DNA and RNA fragments, are prepared from N,O-diprotected nucleosides and a phosphitylation reagent with an activator such as 1H-tetrazole. 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite (1) has been the reagent of frequent choice for phosphitylation due to its ease in handling and safety.1)
References
- 1)Synthesis of protected nucleoside-3'-phosphoramidites using 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite
- a)J. Nielsen, M. Taagaard, J. E. Marugg, J. H. van Boom, O. Dahl, Nucl. Acids Res. 1986, 14, 7391.
- b)I. Okamoto, K. Shohda, K. Seio, M. Sekine, J. Org. Chem. 2003, 68, 9971.
- c)A. Misra, S. Mishra, K. Misra, Bioconjugate Chem. 2004, 15, 638.
- d)R. Gukathasan, M. Massoudipour, I. Gupta, A. Chowdhury, S. Pulst, S. Ratnam, Y. S. Sanghvi, S. A. Laneman, J. Organomet. Chem. 2005, 690, 2603.
- a)J. Nielsen, M. Taagaard, J. E. Marugg, J. H. van Boom, O. Dahl, Nucl. Acids Res. 1986, 14, 7391.
- 2)Multibenzoylated nucleosides for synthesis of small oligonucleotides
Related Compounds
- N,O-Protected nucleosides for DNA and RNA fragments synthesis
- B3103
- N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine
- B3087
- N4-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine
- D3566
- 5'-O-(4,4'-Dimethoxytrityl)thymidine
- I0697
- N2-Isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine
- B3101
- N6-Benzoyl-2'-deoxyadenosine Hydrate
- B3102
- N4-Benzoyl-2'-deoxycytidine
- I0700
- N2-Isobutyryl-2'-deoxyguanosine
- B3093
- N6-Benzoyladenosine
- B3094
- N4-Benzoylcytidine
- I0699
- N2-Isobutyrylguanosine Monohydrate
- B3460
- N6-Dibenzoyladenosine 2',3'-Dibenzoate
- Activators
- B3020
- 5-(Benzylthio)-1H-tetrazole
- D2026
- 4,5-Dicyanoimidazole
- E0670
- 5-(Ethylthio)-1H-tetrazole
- T1017
- 1H-Tetrazole
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