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Biochemistry of Selenium‐Derivatized Naturally Occurring and Unnatural Nucleic Acids
Author(s) -
CatonWilliams Julianne,
Huang Zhen
Publication year - 2008
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200890040
Subject(s) - nucleic acid , chemistry , transfer rna , rna , dna , nucleotide , biochemistry , macromolecule , translation (biology) , nucleic acid structure , amino acid , selenium , stereochemistry , organic chemistry , messenger rna , gene
Selenium (Se) can provide unique biochemical and biological functions, and properties to macromolecules, including protein and RNA. Although Se has not yet been found in DNA, identification of the presence of Se in natural tRNAs has led to discovery of the naturally occurring 2‐selenouridine and 5‐[(methylamino)methyl]‐2‐selenouridine (mnm 5 se 2 U). The Se‐atoms at C(2) of the modified uridines are introduced by 2‐selenouridine synthase via displacement of the S‐atoms in the corresponding 2‐thiouridine nucleotides of the tRNAs, and selenophosphate is used as the Se donor. The research indicated that mnm 5 se 2 U is located at the first or wobble position of the anticodons in several bacterial tRNAs, including tRNA Lys , tRNA Glu , and tRNA Gln . The 2‐seleno functionality on this modified nucleotide probably improves the translation accuracy and/or efficiency. These observations in vivo suggest that the presence of Se can provide natural RNAs with useful properties to better function and survival. To further investigate the biochemical and structural properties of Se‐derivatized nucleic acids (SeNA), we have pioneered chemical and enzymatic synthesis of Se‐derivatized nucleic acids, and introduced Se into both RNA and DNA at a variety of positions by atom‐specific replacement of oxygen. This review outlines the recent advancements in chemical and biochemical syntheses, and studies of SeNAs, and their potential applications in structural and functional investigation of nucleic acids and their protein complexes.