Oligodeoxynucleotides synthesis

There are three widely used chemistries for oligodeoxynucleotide synthesis, and all have been successfully transferred onto SP. The first is the so-called phosphotriester approach (71), which is shown in Fig. 2.9. In this method a 5 -protected nucleoside... 

Phosphorus protection. The protecting group is stable to acid and is removed by fragmentation using aqueous NH4OH. It is introduced by the phosphoramidite approach and is useful for internucleotidic bonds in oligodeoxynucleotide synthesis. 

Table 1 Summary of a 0.2-)amol-Scale Cycle for Oligodeoxynucleotide Synthesis on ABI 394 DNA-RNA Synthesizer ...

As in solution syntheses, two types of strategies have been used for oligodeoxynucleotide synthesis. These are the diester and the triester approaches. The earliest attempts by Letsinger and co-workers employed the triester approach. This is illustrated in Schemes 5-3 and 5-4, X = H). Most of the recent work has employed the diester approach. The advemtage in this particular approach is that the phosphorylating reagents are more reactive than those leading to phosphotriesters. Most workers... 

Fourrey, J L and Varenne, J. (1984) Improved procedure for the preparation of deoxynucleoside phosphoramidites Aiylphosphoramidites as a new convenient intermediates for oligodeoxynucleotide synthesis Tetrahedron Lett, 25,4511-4514... 

Hydrolysis of the activated H-phosphonate leads to the starting nucleoside H-phosphonate, and thus, allows for the recovery and recycling of excess H-phosphonate from oligodeoxynucleotide synthesis. The activated H-phosphonate is quenched into lAf aq. TEAB (pH = 8.5), extracted into CH2CI2, dried over Na2S04, and evaporated. After column chromatography (see above), the H-phosphonate can be reused... 

Synthesis of 3 -C- and 4 -C-branched oligodeoxynucleotides and the development of locked nucleic acids (LNA) 99ACR301. 

Caruthers, M. H., Synthesis of oligonucleotides and oligonucleotide analogues, in Oligodeoxynucleotides — Antisense Inhibitors of Gene Expression, Cohen, J. S., Ed., CRC Press, Boca Raton, FL, 1989, 7. 

Short reviews of die synthesis of oligodeoxynucleotides with mesitylenesulfonyl- or triisopropylbenzenesulfonyltetrazoles as coupling agents are provided in references [26] and [27],... 

B. R. Babu, L. Keinicke, M. Petersen, C. Nielsen, and J. Wengel, 2 -Spiro ribo- and arabinonucleo-sides Synthesis, molecular modelling and incorporation into oligodeoxynucleotides, Org. Biomol. Chem., 1 (2003) 3514-3526. 

DNA synthesis, primed in part by the oligodeoxynucleotide, leads to heteroduplex plasmid circles. (Source After G. Dalbadie-McFarland, L. W. Cohen, A. D. Riggs, C. Morin, K. Itakura, and J. H. Richards, Oligonucleotide-directed mutagenesis as a general and powerful method for studies of protein function, Proc. Natl. Acad. Sci. USA 79 6408-6412, 1982.)... 

Thymidine dimers in which the natural phosphodiester linkage has been replaced by a 2,5-disubstituted tetrazole ring have been synthesized and have been incorporated into oligodeoxynucleotides <02HCA2847>. The synthesis of mono- and bis-3-substituted thymidine derivatives with a polycyclic tetrazole linker (l,5-bis(tetrazol-5-yl)-3-oxapentane) has been reported <02TL1901>. a-Methylene tetrazole-based peptidomimetics were synthesized for inhibition studies of HIV protease <02JCS(P1)172>. A catalytic amount of tetrazole was found to be useful in the syntheses of symmetrical P,P -dialkyl partial esters of methylenebisphosphonic acid from the corresponding acid chloride via a facile two-step, one-... 

Dougherty JP, Rizzo CJ, Breslow R. Oligodeoxynucleotides that contain 2, 5" linkages synthesis and hybridization properties. 

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