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BA 0317
Product Information Molecular Structure


Notes: This phosphoramidite installs a thymidine residue bearing a bulky NPOM protecting group at N1, thus efficiently disrupting Watson-Crick base-pairing. Upon brief exposure to UV light of 365 nm, the "caged" oligonucleotide is uncaged, restoring base-pairing ability.

Description:  Many strategies have surfaced for the caging of oligonucleotides using photochemically labile groups. Caging the nucleobase is particularly attractive.1,2 One of the most promising strategies for doing so involves the use of the 6-nitropiperonyloxymethyl (NPOM) group, installed at N1 of thymidine, as developed by Deiters and co-workers at North Carolina State University.3-5 Thus, NPOM-Caged-dT CEP (BA 0317) was incorporated it into oligonucleotides using standard automated DNA synthesis protocols, resins, and reagents.3,4 The bulky NPOM group was found to effectively block hydrogen-bond formation in duplexes, blocking DNAzyme activity, DNA/RNA hybridization, and allowing the control of PCR amplification. The caged thymidine is stable to a wide range of chemical and physiological conditions, but the NPOM caging group is removed within minutes by irradiation with 365 nm UV light, restoring normal biological function in all cases. This can be achieved using a standard fluorescent microscope, UV LED fiberoptic instruments, or even with a simple hand-held 25 watt UVA lamp. This wavelength is long enough to avoid damage to the oligonucleotides or cells.

Learn more about this phosphoramidite and its use in the control of oligonucleotide function by downloading a Product Information Sheet for BA 0317.

Also in our collection of photolabile tools for oligonucleotide research is the phosphoramidite Caged Strand-Breaker CEP (BA 0315), a monomer that allows the light-induced cleavage of oligonucleotides into two phosphate-terminated daughter strands.

1. Reviews: (a) Mayer, G.; Heckel, A. Angew. Chem. Int. Ed. 2006, 45, 4900-4921. (b) Young, D. D.; Deiters, A. Org. Biomol. Chem. 2007, 5, 999-1005. Tang, X. Dmochowski, I. J. Mol. BioSyst. 2007, 3, 100-110.

2. Examples: (a) Ting, R.; Lermer, L.; Perrin, D. M. J. Am. Chem. Soc. 2004, 126, 12720-12721. (b) Heckel, A.; Meyer, G. J. Am. Chem. Soc. 2005, 127, 822-823. Krock, L.; Heckel, A. Angew. Chem. Int. Ed. 2005, 44, 471-473. (d) Tang, X.; Dmochowski, I. J. Org. Lett. 2005, 7, 279-282. Wenter, P.; Furtig, B.; Hainard, A.; Schwalbe, H.; Pitsch, S. Angew. Chem. Int. Ed. 2005, 44, 2600-2603. (f) Hobartner, C.; Silverman, S. K. Angew. Chem. Int. Ed. 2005, 44, 7305-7309.

3. Lusic, H.; Young, D. D.; Lively, M. O.; Deiters, A. Org. Lett. 2007, 9, 1903-1906.

4. Young, D. D.; Edwards, W. F.; Lusic, H.; Lively, M. O.; Deiters, A. Chem. Commun. 2008, 462-464.

5. Lusic, H.; Deiters, A., Synthesis 2006, 2147-2150.

Product Details Product Pricing

MF: C50H58N5O13P

MW: 967.99

CAS NO: 942218-71-5

Storage Conditions: -20 oC, dry, dark



Stock maintained. Ships within 1-3 days.

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Unit Weight Unit Price Quantity
100 µmol $386.40
0.25 g $766.50
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