Glycerol nucleic acid

Glycerol nucleic acid (GNA) is a chemical similar to DNA or RNA but differing in the composition of its "backbone". GNA is not known to occur naturally in existing life on Earth.

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The 2,3-dihydroxypropylnucleoside analogues were first prepared by Ueda et al (1971). Soon thereafter it was shown that phosphate-linked oligomers of the analogues did in fact exhibit hypochromicity in the presence of RNA and DNA in solution (Seita et al 1972). The preparation of the polymers was later described by Cook et al (1995, 1999) and Acevedo and Andrews (1996). The GNA-GNA self-pairing described by Zhang and Meggers is however novel, and the specificity of interaction well-demonstrated, the molecules themselves.

DNA and RNA have a deoxyribose and ribose sugar backbone, respectively, whereas GNA's backbone is composed of repeating glycerol units linked by phosphodiester bonds. The glycerol molecule has just three carbon atoms and still shows Watson-Crick base pairing. Interestingly, the Watson-Crick base pairing is much more stable in GNA than its natural counterparts DNA and RNA as it requires a high temperature to melt a duplex of GNA. It is possibly the simplest of the nucleic acids, so making it a possible simple precursor to RNA.

References

• Zhang Lilu, Peritz Adam, Meggers Eric (2005). "A simple glycol nucleic acid". J Am Chem Soc 127 (12): 4174-5. PMID 15783191.

Seita, Tooru; Yamauchi, Kiyoshi; Kinoshita, Masayoshi; Imoto, Minoru. Condensation polymerization of nucleotide analogues. Die Makromolekulare Chemie (1972), 154:255-261.

Ueda, Nasuo; Kawabata, Toshio; Takemoto, Kiichi. Synthesis of N-(2,3-dihydroxypropyl) derivatives of nucleic bases. Journal of Heterocyclic Chemistry (1971), 8(5), 827-9.

Acevedo, Oscar L.; Andrews, Robert S. Synthesis of propane-2,3-diol combinatorial monomers. Tetrahedron Letters (1996), 37(23), 3931-3934.

Cook, Phillip Dan; Acevedo, Oscar L.; Davis, Peter W.; Ecker, David J.; Hebert, Normand. Synthesis of acyclic oligonucleotides as antiviral and antiinflammatory agents and inhibitors of phospholipase A2. PCT Int. Appl. (1995), 126 pp. WO 9518820 A1 19950713 CAN 124:30276 AN 1995:982328

Cook, Phillip Dan; Acevedo, Oscar L.; Davis, Peter W.; Ecker, David J.; Hebert, Normand. Preparation of ethylene glycol phosphate linked oligodeoxyribonucleotides as phospholipase A2 inhibitors. U.S. (1999), 39 pp., Cont.-in-part of U.S. Ser. No. 179,970. CODEN: USXXAM US 5886177 A 19990323 CAN 130:237811 AN 1999:205354