Triple helices formed by polyuridylic acid with some adenosine derivatives

Shim, Jaewon L.; Lohrmann, R.; Orgel, Leslie E.

doi:10.1007/bf01732516

Cited by 7 publications

(5 citation statements)

References 11 publications

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“…Finally, our experiments demonstrate again the significance of the humidity for prebiotic reactions (Lohrmann, 1975;Lohrmann, 1976). In dilute solutions we usually observe little reaction, but in concentrated solution we can, for example, demonstrate the formation of ImpA from ATP and imidazole.…”

Section: Prebiological Significancementioning

confidence: 78%

“…There are a number of routes that make possible the formation of nucleoside 5'-polyphosphates from nucleosides and inorganic phosphates under potentially prebiotic conditions (Kenyon and Steinman, 1969;Neuman and Neuman, 1970;0sterberg et al, 1973 ;Handschuh et al, 1973;Lohrmann, 1975 ;Lohrmann, 1976). The demonstration that many amines react efficiently with "prebiotic" polyphosphates to give phos-phoramidates is, therefore, of considerable interest.…”

Section: Prebiological Significancementioning

confidence: 97%

“…14C-labelled pA was first reacted with trimetaphosphate under conditions which had been found previously to give good yields of polyphosphates (Lohrmann, 1975). Table 4 shows that after 3 days at room temperature and 70 % humidity, 87.5 % of the radioactivity was in the form of adenosine 5Lpolyphosphates pn A (n >~ 3).…”

Section: Reaction Of Adenosine 5'-polyphosphates With Imidazolementioning

confidence: 99%

“…Blum, 1951 ;Kenyon and Steinman, 1969;Ponnamperuma, 1972;papers in Buvet and Ponnamperuma, 1971) have suggested that the primary source of free energy for prebiological systems was a mixture of organic and/or inorganic polyphosphates. In previous papers we showed how organic polyphosphates could have formed under potentially prebiotic conditions (Lohrmann, 1975;Lohrmann, 1976) and how they can be used to activate amino acids (Sawai et al, 1975;Sawai and Orgel, 1975). In addition, we published a preliminary report …”

Section: Introductionmentioning

confidence: 94%

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Formation of nucleoside 5′-phosphoramidates under potentially prebiological conditions

Lohrmann

1977

J Mol Evol

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Adenosine 5'-phosphoramidates form when solutions containing adenosine 5'-polyphosphates pnA (n greater than or equal to 3) or P1, P2-diadenosine 5'-diphosphate and amines are allowed to dry out. Mg ions catalyze these reactions. We have studied systems containing ammonia, imidazole, glycine, ethylenediamine and histamine. The yields of adenosine 5'-phosphoramidates range from 10-50% based on the nucleotide. The prebiotic significance of the reactions is discussed.

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Section: Prebiological Significancementioning

confidence: 78%

Section: Prebiological Significancementioning

confidence: 97%

Section: Reaction Of Adenosine 5'-polyphosphates With Imidazolementioning

confidence: 99%

Section: Introductionmentioning

confidence: 94%

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Formation of nucleoside 5′-phosphoramidates under potentially prebiological conditions

Lohrmann

1977

J Mol Evol

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“…ImpA (Shim et al, 1975). The poly(U) template, which is exclusively composed of D-uridine, facilitates the formation of oligoadenylates from D-ImpA as reported previously by Orgel et al (Weiman et al, 1968;Schneider-Bernloher et al, 1970;Orgel and Lohrmann, 1973).…”

Section: Resultsmentioning

confidence: 76%

Chiral Selection in Oligoadenylate Formation in the Presence of a Metal ion Catalyst or Poly(U) Template

Osawa

Urata

Sawai

2005

Orig Life Evol Biosph

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The lead ion-catalyzed oligomerization of 5'-phosphorimidazolides of D-, L- or racemic DL-adenosine (D-ImpA, L-ImpA and DL-ImpA) gave oligoadenylates up to a pentamer. The oligomers resulting from racemic ImpA were comparable in yields and length to those from chiral D- or L-ImpA. A complex mixture of homochiral and heterochiral oligomers was formed in the reaction from racemic ImpA. Total dimer product from racemic ImpA by the lead ion catalyst showed homochiral selectivity. The reaction catalyzed by uranyl ion yielded oligoadenylates up to 15mer from chiral D- or L-ImpA in over 95% yield. A complex mixture of isomeric oligoadenylates was formed from racemic DL-ImpA in the presence of uranyl ion catalyst in comparable yields to those from D- or L-ImpA. The analysis of the dimer product from DL-ImpA showed that the homochiral 2' -5' linked dimer was selectively formed. D-ImpA polymerized effectively on a poly(U) template, which is exclusively composed of D-uridine, yielding oligoadenylates up to a pentamer. In contrast, L-ImpA or racemic DL-ImpA polymerized far less efficiently on the poly(U) template, demonstrating that chiral selection takes place in the poly(U) template-directed oligoadenylate formation.

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Studies of oligoadenylate formation on a poly(U) template

Lohrmann

Orgel

1979

J Mol Evol

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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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Triple helices formed by polyuridylic acid with some adenosine derivatives

Cited by 7 publications

References 11 publications

Formation of nucleoside 5′-phosphoramidates under potentially prebiological conditions

Formation of nucleoside 5′-phosphoramidates under potentially prebiological conditions

Chiral Selection in Oligoadenylate Formation in the Presence of a Metal ion Catalyst or Poly(U) Template

Studies of oligoadenylate formation on a poly(U) template

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