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  • 1
    Electronic Resource
    Electronic Resource
    Template-catalyzed oligomerization with an atactic glycerol-based polynucleotide analog (1990)
    Springer
    Journal of molecular evolution 31 (1990), S. 163-166 
    Details
    ISSN: 1432-1432
    Keywords: Chemical evolution ; Nucleic acid analogs ; Oligonucleotides ; Template-directed synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary We have tested the effect of a nonstereoregular (atactic) template, based on the acyclic nucleotide analog $$p\tilde Cp$$ , on the oligomerization of the complementary bis-phosphoimidazolide monomer, $$Imp\tilde GpIm$$ . Although there is little catalysis when the template is added together with magnesium ions, the substitution of manganese for magnesium produces a substantial increase in the extent of oligomerization as well as increasing the effect of the template. These results are discussed in relation to the hypothesis that prochiral nucleotide analogs may have been precursors to the first RNA molecules.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02109491
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  • 2
    Electronic Resource
    Electronic Resource
    Nucleic acid-like structures III. Oligomerization of 3′-deoxyadenosine 2′,5′-diphosphoimidazolide (1987)
    Springer
    Journal of molecular evolution 26 (1987), S. 291-293 
    Details
    ISSN: 1432-1432
    Keywords: Chemical evolution ; Template synthesis ; Polynucleotides ; Nucleotide oligomerization ; Nucleic acid analogues
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary The activated dimonophosphate of 3′-deoxyadenosine (cordycepin) undergoes oligomerization to produce a new family of pyrophosphate-linked oligomers in which the average repeating unit involves a nine-atom structural group. The presence of a poly(U) template increase the relative yields of higher oligomers, although the template-free reaction is itself extremely efficient.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02101146
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  • 3
    Electronic Resource
    Electronic Resource
    Template-directed synthesis of acyclic oligonucleotide analogues (1988)
    Springer
    Journal of molecular evolution 28 (1988), S. 3-6 
    Details
    ISSN: 1432-1432
    Keywords: Chemical evolution ; Template synthesis ; Oligonucleotides ; Nucleic acid analogues
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Bis-phosphoimidazolides of an analogue of adenosine (in which ribose is replaced by an acyclic chain) and of two related analogues of guanosine undergo oligomerization in the presence of complementary polynucleotide templates. Data on the template- and nontemplate-directed reactions are presented, and the possible relevance to origins of life is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02143492
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  • 4
    Electronic Resource
    Electronic Resource
    An achiral (oligo)nucleotide analog (1994)
    Springer
    Journal of molecular evolution 38 (1994), S. 438-442 
    Details
    ISSN: 1432-1432
    Keywords: Nucleotide analogs ; Oligomerization ; Chirality ; Barbituric acid ; Pentaerythritol ; Prebiotic chemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: 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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00178843
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  • 5
    Electronic Resource
    Electronic Resource
    Reactive Phosphonic Acids as Prebiotic Carriers of Phosphorus (1997)
    Springer
    Journal of molecular evolution 44 (1997), S. 237 -241 
    Details
    ISSN: 1432-1432
    Keywords: Key words: Prebiotic chemistry — Nucleotide analogues — Phosphonic acids — Photochemistry — Ribose
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract. Phosphonic acids are the only phosphorus-containing organic compounds detected in the Murchison meteorite. We earlier described the synthesis of methyl-, hydroxymethyl-, and 1-hydroxyethyl phosphonic acids using sodium phosphite as a source of phosphite radicals. We now show that ultraviolet irradiation of dilute aqueous solutions of acetylene in the presence of sodium phosphite leads to the synthesis of vinyl phosphonic acid. At neutral to basic pH, vinyl phosphonic acid reacts under photochemical conditions to produce phosphonoacetaldehyde and 2-hydroxyethyl phosphonic acid as the major products, as well as smaller yields of 1-hydroxyethyl phosphonic acid, phosphonoacetic acid, and ethyl phosphonic acid. Of these products, phosphonoacetaldehyde is particularly interesting as a potential precursor of prebiotic carbohydrate derivatives.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/PL00006140
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  • 6
    Electronic Resource
    Electronic Resource
    Template-directed polynucleotide synthesis on mineral surfaces (1985)
    Springer
    Journal of molecular evolution 21 (1985), S. 299-300 
    Details
    ISSN: 1432-1432
    Keywords: Chemical evolution ; Template synthesis ; Minerals ; Polynucleotides ; Nucleotide oligomerization
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Ferric hydroxide, a plausible prebiotic material, strongly adsorbs polynucleotides. We show that adsorption on ferric hydroxide and on several other minerals has no effect, under the conditions studies, on the template-directed oligomerization of guanylic acid on polycytidylic acid.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02102362
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  • 7
    Electronic Resource
    Electronic Resource
    Acceleration of HCN oligomerization by formaldehyde and related compounds: Implications for prebiotic syntheses (1982)
    Springer
    Journal of molecular evolution 18 (1982), S. 351-353 
    Details
    ISSN: 1432-1432
    Keywords: HCN ; HCN Oligomers ; Chemical Evolution ; Primitive Earth ; Formaldehyde ; Cyanohydrins ; Catalysis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Formaldehyde and other simple carbonyl compounds are known to react rapidly with HCN in aqueous solution to produce the corresponding cyanohydrin compounds. We have observed that these cyanohydrins markedly accelerate the rate of HCN oligomeri-zation, both in homogeneous solution as well as in the frozen state. These results, for which a tentative mechanism is suggested, significantly extend the possible range of conditions for HCN oligomerization on the prebiotic Earth.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01733902
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  • 8
    Electronic Resource
    Electronic Resource
    Mineral Catalysis of a Potentially Prebiotic Aldol Condensation (1998)
    Springer
    Journal of molecular evolution 47 (1998), S. 501-507 
    Details
    ISSN: 1432-1432
    Keywords: Key words: Aldol condensation — Chemical evolution — Origin of life — Double-layer hydroxide minerals — Phosphonic acids
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract. Minerals may have played a significant role in chemical evolution. In the course of investigating the chemistry of phosphonoacetaldehyde (PAL), an analogue of glycolaldehyde phosphate, we have observed a striking case of catalysis by the layered hydroxide mineral hydrotalcite ([Mg2Al(OH)6][Cl.nH2O]). In neutral or moderately basic aqueous solutions, PAL is unreactive even at a concentration of 0.1 M. In the presence of a large excess of NaOH (2 M), the compound undergoes aldol condensation to produce a dimer containing a C3–C4 double-bond. In dilute neutral solutions and in the presence of the mineral, however, condensation takes place rapidly, to produce a dimer which is almost exclusively the C2–C3 unsaturated product.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/PL00006406
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  • 9
    Electronic Resource
    Electronic Resource
    Manganese-catalyzed oligomerizations of nucleotide analogs (1989)
    Springer
    Journal of molecular evolution 29 (1989), S. 284-287 
    Details
    ISSN: 1432-1432
    Keywords: Chemical evolution ; Nucleic acid analogs ; Oligonucleotides ; Metal ion catalysis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary The synthesis of pyrophosphate-linked oligomers from the bis-phosphoimidazolides of deoxyadenosine and deoxyguanosine, as well as from acyclic analogs of these nucleosides, is catalyzed much more effectively by Mn(II) than by Mg(II). The presence of Mn(II) reduces the extent of cyclization of the monomer-bis-phosphoimidazolide and thereby increases the yields of oligomeric products. The Mn(II)-catalyzed oligomerization is less sensitive to the presence of a complementary polynucleotide template than is the Mg(II)-catalyzed reaction.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02103615
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  • 10
    Electronic Resource
    Electronic Resource
    Oligomerization of cytosine-containing nucleotide analogs in aqueous solution (1990)
    Springer
    Journal of molecular evolution 30 (1990), S. 3-6 
    Details
    ISSN: 1432-1432
    Keywords: Chemical evolution ; Nucleic acid analogs ; Oligonucleotides ; Metal ion catalysis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Bisphosphoimidazolides of 2′-deoxycytidine and of its acyclic analog $$\tilde C$$ can be oligomerized in aqueous solution in the presence of Mn(II). Under certain conditions, a range of products extending to at least the 20mer can be obtained. These products are of interest as possible templates for oligomerization of the complementary monomers.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02102447
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