Synthesis and Crystal Structure of 2′-Se-Modified Guanosine Containing DNA

• Published in: Journal of organic chemistry Vol. 75; no. 3; pp. 637 - 641
• Main Authors: Salon, Jozef, Sheng, Jia, Gan, Jianhua, Huang, Zhen
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 05.02.2010; Amer Chemical Soc
• Subjects: Analytical, structural and metabolic biochemistry; BASIC BIOLOGICAL SCIENCES; Biological and medical sciences; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Organic; CRYSTAL GROWTH; CRYSTAL STRUCTURE; Crystallography, X-Ray; Deoxyguanosine - analogs & derivatives; Deoxyguanosine - chemical synthesis; Deoxyguanosine - chemistry; DNA; DNA - chemical synthesis; DNA - chemistry; Dna, deoxyribonucleoproteins; Exact sciences and technology; FUNCTIONALS; Fundamental and applied biological sciences. Psychology; GENERAL AND MISCELLANEOUS//MATHEMATICS, COMPUTING, AND INFORMATION SCIENCE; GUANOSINE; Guanosine - chemical synthesis; Guanosine - chemistry; Models, Molecular; MODIFICATIONS; national synchrotron light source; Nucleic Acid Conformation; NUCLEIC ACIDS; Nucleosides, nucleotides and oligonucleotides; Organic chemistry; Organoselenium Compounds - chemical synthesis; Organoselenium Compounds - chemistry; Physical Sciences; Preparations and properties; RESOLUTION; Science & Technology; SELENIUM; SYNTHESIS; CRYSTALLIZATION; MAD; ANOMALOUS DIFFRACTION; RNA; NUCLEOSIDES; SELENIUM DERIVATIZATION; CRYSTALLOGRAPHY; PHOSPHORAMIDITE; NUCLEIC-ACIDS; OLIGONUCLEOTIDES; Crystal growth; Organic selenide; Molecular structure; DNA; Organic phosphoramidite; Nucleoside; Selenium; Chemical synthesis; X ray diffraction; Nucleic acid; Phosphorus Organic compounds; Crystalline structure
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo902190c

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 SeTACAC-3′) was determined at a resolution of 1.20 Å. 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.