Albany 2015:Book of Abstracts

Albany 2015
Conversation 19
June 9-13 2015
©Adenine Press (2012)

Synthesis and Base Pairing Studies of Geranylated DNA and RNA

RNA plays essential roles in living systems and dramatically expands the complexity of life as genetic information carrier, catalyst, and regulator. These RNA functions are mainly achieved by the diversified and well-defined 3D structures derived from specific base-base recognition and interaction. Nature uses modified nucleobases to increase the specificity and diversity of RNA base-base interactions. Over 140 post-transcriptional modifications have been discovered so far in mRNA, rRNA, tRNA, and non-coding RNAs. Studying the structures and energetics of base pairing containing modified nucleobases is significant for the further elucidation of RNA functions, the development of new RNA-based therapeutics, and the study of the origins of life.

Very recently, two hydrophobic 5-substituted-2-thiouridines in which the sulfur atom is functionalized with a geranyl residue were identified in several bacterial strains at position 34 of tRNAs specific for lysine, glutamine and glutamic acid. The geranylation of the wobble S2U nucleoside affects the codon preference and frame shifting during translation. Selenouridine synthase SelU, which can install selenium into the position 2 of 2-thiouridine, is the responsible enzyme for this geranylation. It is quite interesting that the same enzyme can carry out two different reactions using the same substrates. We presented herein our preliminary synthesis and base pairing studies of these geranylated DNA and RNA.

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Rui Wang
Fusheng Shen
Stephanie M. Magliocco
Vibhav A. Valsangkar
Jia Sheng*

Department of Chemistry
RNA Institute
University at Albany
State University of New York
Albany, NY 12222

Phone: (518) 437-4419