Chemical Phosphorylation Reagent II (CPR II)

Product description

Solvent：MeCN,DMSO

MW : 722.8

Features and Biological Applications

This Chemical Phosphorylation Reagent (CPR II) contains a DMT group that can be left on the oligonucleotide and used for rapid purification of oligonucleotide 5′-phosphates by the popular DMTr-on technique, which employs disposable RP cartridges or “Trityl-on” RP HPLC purification. The DMTr group is removed with aqueous acid (e.g., 2%TFA in the case of Cartridge Purification) and the remaining linker is then eliminated after brief treatment with aqueous ammonium hydroxide (12 -15% ammonium hydroxide at room temperature for 15 minutes) to yield the 5′-phosphate.

References

1. Xu Y, Lee SA, Kutateladze TG, Sbrissa D, Shisheva A, Prestwich GD. (2006) Chemical synthesis and molecular recognition of phosphatase-resistant analogues of phosphatidylinositol-3-phosphate. J Am Chem Soc, 128, 885.

2. Ohkubo A, Ezawa Y, Seio K, Sekine M. (2004) O-selectivity and utility of phosphorylation mediated by phosphite triester intermediates in the N-unprotected phosphoramidite method. J Am Chem Soc, 126, 10884.

3. Tsuruoka H, Shohda K, Wada T, Sekine M. (2000) Synthesis and conformational properties of oligonucleotides incorporating 2′-O-phosphorylated ribonucleotides as structural motifs of pre-tRNA splicing intermediates. J Org Chem, 65, 7479.

4. Olejnik J, Krzymanska-Olejnik E, Rothschild KJ. (1996) Photocleavable biotin phosphoramidite for 5′-end-labeling, affinity purification and phosphorylation of synthetic oligonucleotides. Nucleic Acids Res, 24, 361.

5. Mora N, Lacombe JM, Pavia AA. (1995) A new approach to phosphoserine, phosphothreonine and phosphotyrosine synthons and to thiophospho analogs. Stepwise synthesis of mono- and multiphosphorylated phosphopeptides related to src-protein kinase. Int J Pept Protein Res, 45, 53.

6.  Boumendjel A, Miller SP. (1994) Synthesis of sphingosine-1-phosphate and dihydrosphingosine-1-phosphate. J Lipid Res, 35, 2305.

7. Kitas E, Kung E, Bannwarth W. (1994) Chemical synthesis of O-thiophosphotyrosyl peptides. Int J Pept Protein Res, 43, 146.

8. Tegge W, Ballou CE. (1992) Syntheses of D-myo-inositol 1,4,5-trisphosphate affinity ligands. Carbohydr Res, 230, 63.

9. Perich JW, Reynolds EC. (1991) Fmoc/solid-phase synthesis of Tyr(P)-containing peptides through t-butyl phosphate protection. Int J Pept Protein Res, 37, 572.

10. Lacombe JM, Andriamanampisoa F, Pavia AA. (1990) Solid-phase synthesis of peptides containing phosphoserine using phosphate tert.-butyl protecting group. Int J Pept Protein Res, 36, 275.

Product description

Solvent：MeCN,DMSO

MW : 722.8

Features and Biological Applications

This Chemical Phosphorylation Reagent (CPR II) contains a DMT group that can be left on the oligonucleotide and used for rapid purification of oligonucleotide 5′-phosphates by the popular DMTr-on technique, which employs disposable RP cartridges or “Trityl-on” RP HPLC purification. The DMTr group is removed with aqueous acid (e.g., 2%TFA in the case of Cartridge Purification) and the remaining linker is then eliminated after brief treatment with aqueous ammonium hydroxide (12 -15% ammonium hydroxide at room temperature for 15 minutes) to yield the 5′-phosphate.

References

1. Xu Y, Lee SA, Kutateladze TG, Sbrissa D, Shisheva A, Prestwich GD. (2006) Chemical synthesis and molecular recognition of phosphatase-resistant analogues of phosphatidylinositol-3-phosphate. J Am Chem Soc, 128, 885.

2. Ohkubo A, Ezawa Y, Seio K, Sekine M. (2004) O-selectivity and utility of phosphorylation mediated by phosphite triester intermediates in the N-unprotected phosphoramidite method. J Am Chem Soc, 126, 10884.

3. Tsuruoka H, Shohda K, Wada T, Sekine M. (2000) Synthesis and conformational properties of oligonucleotides incorporating 2′-O-phosphorylated ribonucleotides as structural motifs of pre-tRNA splicing intermediates. J Org Chem, 65, 7479.

4. Olejnik J, Krzymanska-Olejnik E, Rothschild KJ. (1996) Photocleavable biotin phosphoramidite for 5′-end-labeling, affinity purification and phosphorylation of synthetic oligonucleotides. Nucleic Acids Res, 24, 361.

5. Mora N, Lacombe JM, Pavia AA. (1995) A new approach to phosphoserine, phosphothreonine and phosphotyrosine synthons and to thiophospho analogs. Stepwise synthesis of mono- and multiphosphorylated phosphopeptides related to src-protein kinase. Int J Pept Protein Res, 45, 53.

6.  Boumendjel A, Miller SP. (1994) Synthesis of sphingosine-1-phosphate and dihydrosphingosine-1-phosphate. J Lipid Res, 35, 2305.

7. Kitas E, Kung E, Bannwarth W. (1994) Chemical synthesis of O-thiophosphotyrosyl peptides. Int J Pept Protein Res, 43, 146.

8. Tegge W, Ballou CE. (1992) Syntheses of D-myo-inositol 1,4,5-trisphosphate affinity ligands. Carbohydr Res, 230, 63.

9. Perich JW, Reynolds EC. (1991) Fmoc/solid-phase synthesis of Tyr(P)-containing peptides through t-butyl phosphate protection. Int J Pept Protein Res, 37, 572.

10. Lacombe JM, Andriamanampisoa F, Pavia AA. (1990) Solid-phase synthesis of peptides containing phosphoserine using phosphate tert.-butyl protecting group. Int J Pept Protein Res, 36, 275.