Summary
When 2′-deoxythymidine-3′,5′-cyclic diphosphate, or the cyclic pyrophosphates of the acyclic nucleoside analogues II and IV are heated to 65–85°C in the presence of imidazole, oligomers with lengths up to 20–30 are formed in excellent yield. This reaction provides a useful source of oligomers for use as templates in aqueous condensation reactions. In the absence of evidence to the contrary, we assume that the oligomers are atactic. The potential significance of this reaction in prebiotic chemistry is discussed.
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Abbreviations
- Im:
-
imidazole
- EDAC:
-
1-ethyl-3(3-dimethylaminopropyl)-carbodiimide hydrochloride
- EDTA:
-
ethylenediaminetetraacetic acid
- TEAB:
-
triethylammonium bicarbonate
- poly(C):
-
polycytidylic acid
- poly(U):
-
polyuridylic acid
- A:
-
adenine
- G:
-
guanine
- \(p\mathop A\limits^ = p!\) :
-
9-[3-hydroxy-2-(hydroxymethyl)prop-1-yl]adenine cyclic diphosphate
- \(p\mathop G\limits^ = p!\) :
-
9-[3-hydroxy-2-(hydroxymethyl)prop-1-yl]guanine cyclic diphosphate
- pTp!:
-
2′-deoxythymidine-3′,5′-cyclic diphosphate
- pPrp!:
-
1,3-propanediol cyclic diphosphate
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Tohidi, M., Orgel, L.E. Polymerization of the cyclic pyrophosphates of nucleosides and their analogues. J Mol Evol 30, 97–103 (1990). https://doi.org/10.1007/BF02099935
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DOI: https://doi.org/10.1007/BF02099935