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BA 0300
Product Information Molecular Structure

Anthraquinone-pyrrolidine CEP

Notes:  Anthraquinone-Pyrrolidine CEP is a 3-hydroxyprolinol analog bearing an anthraquinone amide at the pyrrolidine amino group. The anthraquinone pyrrolidine can be installed internally or at the 5'-terminus of an oligonucleotide.

Description: Anthraquinones may be incorporated into oligonucleotides by a variety of methods using a host of different phosphoramidites. The anthraquinone moiety is useful for applications such as intercalation, duplex and triplex stabilization, photochemical immobilization, quenching of fluorescence, electrochemical detection, and charge transport through nucleic acids. Of the various anthraquinone phosphoramidites that have been explored, amide formation at the carboxyl group of anthraquinone-2-carboxylic acid is popular.1-8

Hydroxyprolinol has found use as a substitute for the sugar ring of nucleotides.9-10 We now offer Anthraquinone-pyrrolidine CEP, a 3-hydroxyprolinol analog bearing an anthraquinone amide at the pyrrolidine amino group. The anthraquinone pyrrolidine can be installed internally or at the 5'-terminus of an oligonucleotide.

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1. (a) Gasper, S. M.; Schuster, G. B. J. Am. Chem. Soc. 1997, 119, 12762-12771. (b) Shao, F.; Augustyn, K.; Barton, J. K. J. Am. Chem. Soc. 2005, 127, 17445-17452.

2. Whittemore, N. A.; Mullenix, A. N.; Inamati, G. B.; Manoharan, M.; Cook, P. D.; Tuinman, A. A.; Baker, D. C.; Chambers, J. Q. Bioconj. Chem. 1999, 10, 261-270.

3. Tierney, M. T.; Grinstaff, M. W. Org. Lett. 2000, 2, 3413-3416.

4. Tierney, M. T.; Grinstaff, M. W. J. Org. Chem. 2000, 65, 5355-5359.

5. Koch, T.; Jacobsen, N.; Fensholdt, J.; Boas, U.; Fenger, M.; Jakobsen, M. H. Bioconj. Chem. 2000, 11, 474-483.

6. Al-Rawi, S.; Ahlborn, C.; Richert, C. Org. Lett. 2005, 7, 1569-1572.

7. Asanuma, H.; Hayashi, H.; Zhao, J.; Liang, X.; Yamazawa, A.; Kuramochi, T.; Matsunaga, D.; Aiba, Y.; Kashida, H.; Komiyama, M. Chem. Commun. 2006, 5062-5064.

8. Shibata, A.; Ueno, Y.; Shinbo, K.; Nakanishi, M.; Matsuda, A.; Kitade, Y. Bioorg. Med. Chem. Lett. 2006, 16, 1410-1413.

9. Ceulemans, G.; Van Aerschot, A.; Rozenski, J.; Herdewijn, P. Tetrahedron 1997, 53, 14957-14974.

10. Scharer, O. D.; Ortholand, J.-P.; Ganesan, A.; Ezaz-Nikpay, K.; Verdine, G. L. J. Am. Chem. Soc. 1995, 117, 6623-6624.

Anthraquinone-pyrrolidine CEP
Product Details Product Pricing

MF: C50H52N3O8P

MW: 853.94

CAS NO: 1221186-23-7

Storage Conditions: Dry, -20 C, dark

Purity≥90%

Availability: 

Stock maintained. Ships within 1-3 days.

Unit Weight Unit Price Quantity
100 µmol $395.00
0.25 g $895.00
 
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