Summary information and primary citation
- PDB-id
- 3bm0; DSSR-derived features in text and JSON formats
- Class
- DNA
- Method
- X-ray (1.8 Å)
- Summary
- Structure of DNA octamer g(duse)g(5-sedu)acac
- Reference
- Hassan AE, Sheng J, Jiang J, Zhang W, Huang Z (2009): "Synthesis and crystallographic analysis of 5-Se-thymidine DNAs." Org.Lett., 11, 2503-2506. doi: 10.1021/ol9004867.
- Abstract
- We investigated the possibility of the interaction of 5-CH(3) of thymidine and its 5'-phosphate backbone (C-H...O(-)-PO(3) interaction) in DNA via the insertion of the atomic probe (a selenium atom) into the exo-5-position of thymidine (5-Se-T). 5-Se-T was synthesized for the first time, via Mn(OAc)(3) assisted electrophilic addition of CH(3)SeSeCH(3) to 3',5'-di-O-benzoyl-2'-deoxyuridine. The 5-Se-T phosphoramidite was subsequently synthesized and incorporated into DNA in over 99% coupling yield. Biophysical and structural investigations of the 5-Se-T DNAs revealed that the Se-modified and nonmodified DNAs are virtually identical. In addition, the crystallographic analysis of a 5-Se-T DNA strongly suggests a hydrogen-bond formation between the 5-CH(3) and 5'-phosphate groups (CH(3)...PO(4)(-) interaction).
