Synthesis and crystal structure of 2'-se-modified guanosine containing DNA.
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 A. 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.
Salon
Jozef
J
Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA.
Sheng
Jia
J
Gan
Jianhua
J
Huang
Zhen
Z
D018360:Crystallography, X-Ray; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006151:Guanosine / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
C548323:2'-selenomethyl-2'-deoxyguanosine; D016566:Organoselenium Compounds; D006151:Guanosine; D004247:DNA; D003849:Deoxyguanosine