Synthesis and Crystallographic Analysis of 5-Se-Thymidine DNAs

Journal Article · Thu Jan 01 04:00:00 EST 2009 · Organic Letters

DOI:https://doi.org/10.1021/ol9004867· OSTI ID:980600

Hassan, A; Sheng, J; Jiang, J; Zhanbg, W; Huang, Z

We investigated the possibility of the interaction of 5-CH3 of thymidine and its 5?-phosphate backbone (C-H O-PO3 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 CH3SeSeCH3 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-CH3 and 5?-phosphate groups (CH3 PO4- interaction).

• Research Organization: Brookhaven National Laboratory (BNL) National Synchrotron Light Source
• Sponsoring Organization: Doe - Office Of Science
• DOE Contract Number: AC02-98CH10886
• OSTI ID: 980600
• Report Number(s): BNL--93518-2010-JA
• Journal Information: Organic Letters, Journal Name: Organic Letters Journal Issue: 12 Vol. 11; ISSN 1523-7060
• Country of Publication: United States
• Language: English

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
99 GENERAL AND MISCELLANEOUS
COUPLING
DNA
INTERACTIONS
SELENIUM
SYNTHESIS
THYMIDINE
national synchrotron light source