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Studies of oligoadenylate formation on a poly(U) template

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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

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