Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 3, Pages 637-641Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo902190c
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Funding
- U.S. National Science Foundation (NSF) [MCB-0824837]
- Georgia Cancer Coalition (GCC) Distinguished Cancer Clinicians and Scientists
- Direct For Biological Sciences
- Div Of Molecular and Cellular Bioscience [0824837] Funding Source: National Science Foundation
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Selenium modification of nucleic acids is of great importance in X-ray crystal structure determination and functional study of nucleic acids. Herein, we describe a convenient synthesis of a new building block, the 2'-SeMe-modified guanosine (G(Se)) phosphoramidite, and report the first incorporation of the 2'-Se-G moiety into DNA. The X-ray crystal structure of the 2'-Se-modified octamer DNA (5'-GTG(Se)TACAC-3') was determined at a resolution of 1.20 angstrom. We also found that the 2'-Se modification points to the minor groove and that the modified and native structures are virtually identical. Furthermore, we observed that the 2'-Se-G modification can significantly facilitate the crystal growth with respect to the corresponding native DNA.
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