Summary
We have studied a variety of condensation reactions involving poly (U) as template and isomeric adenosine dinucleotides as substrates. We find that [3′–5′]-linked dinucleotides such as A3pA and pA3pA are better acceptors than the corresponding [2′–5′]-linked compounds, while ImpA2pA is a better donor than ImpA3pA. The reaction between A2pA and ImpA3pA, for example, yields only 4% of product while the reaction of A3pA with ImpA2pA yields 86% of product.
The more efficient condensation reactions of dimers are about as efficient as the self-condensation of ImpA. They yield a few percent of material in which five or more substrate molecules are linked together. The percentage of the natural [3′–5′]-linkage in the product varies greatly, from as little as 1% to as much as 45%.
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Abbreviations
- Im:
-
imidazole
- MeIm:
-
1-methylimidazole
- A:
-
adenosine
- pA:
-
adenosine 5′-phosphate
- MepA:
-
adenosine 5′-(phosphoric acid methylester)
- Ap:
-
adenosine 2′,(3′)-phosphate
- A>p:
-
adenosine cyclic 2′,3′-phosphate
- ImpA:
-
adenosine 5′-phosphorimidazolide
- (pA)n(n=2,3⋯):
-
oligomers of pA
- (Ap)n(n=2,3⋯):
-
oligomers of Ap
- H2N-pApA:
-
5′-amidate of a diadenylate pApA
- ImpApA:
-
5′-imidazolide of a diadenylate pApA
- A(pA)n :
-
oligoadenylates terminated by a free 5′-OH group
- Me(pA)n(n=1,2⋯):
-
5′-methylester of an oligoadenylate (pA)n
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The numbers given as superscripts between a nucleoside and a phosphate indicates the type of internucleotide linkage, e.g. A2pA3pA is adenylyl-[2′→5′]-adenylyl-[3′→5′]-adenosine; poly(U), polyuridylic acid. A star above the symbol for a nucleoside indicates the position of the radioactive label, e.g. A2pA, [8-14C]-adenylyl-[2′→5′]-adenosine. ODU, optical density units measured at 259 nm. BAP, bacterial alkaline phosphatase (E. coli).
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Lohrmann, R., Orgel, L.E. Studies of oligoadenylate formation on a poly(U) template. J Mol Evol 12, 237–257 (1979). https://doi.org/10.1007/BF01732341
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DOI: https://doi.org/10.1007/BF01732341