Abstract
An achiral nucleotide analog based on barbituric acid has been synthesized. The analog, which is 5,5-di(2-phosphoethyl)barbituric acid, undergoes extensive oligomerization in aqueous solution, when activated, to produce pyrophosphate-linked chains. In contrast to a number of other bisphosphorylated nucleoside analogs which have been studied, the compound has little tendency to cyclize. The possible prebiotic implications are discussed.
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Abbreviations
- TEAB:
-
triethylammonium bicarbonate
- EDTA:
-
ethylene diamine tetraacetic acid
- TEA:
-
triethylamine
- DMF:
-
dimethylformamide
- DMSO:
-
dimethylsulfoxide
- Im:
-
imidazole
- Tris:
-
tris(hydroxymethyl)aminomethane
- \(\widetilde{\text{C}}\) :
-
1-(1,3-dihydroxy-2propoxy)methyl]cytosine
- p\(\widetilde{\text{C}}\)p:
-
the bisphosphate of \(\widetilde{\text{C}}\)
- \(\widetilde{\text{G}}\) :
-
9-[(1,3-dihydroxy-2-propoxy)methyl]guanine
- 2:
-
5,5-di(2-hydroxyethyl)-2,4,6pyrimidinetrione
- p2p:
-
the bisphosphate of 2
- Imp2pIM:
-
the bisphosphoimidazolide of 2
- Imp\(\widetilde{\text{G}}\)pIM:
-
the bisphosphoimidazolide of \(\widetilde{\text{G}}\)
- AppA:
-
diadenosine-5′,5′-pyrophosphate
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Correspondence to: AM. Schwartz
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van Vliet, M.J., Visscher, J. & Schwartz, A.W. An achiral (oligo)nucleotide analog. J Mol Evol 38, 438–442 (1994). https://doi.org/10.1007/BF00178843
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DOI: https://doi.org/10.1007/BF00178843