Catalysts for the self-polymerization of adenosine cyclic 2′,3′-phosphate

Verlander, Michael S.; Lohrmann, R.; Orgel, Leslie E.

doi:10.1007/bf01654098

Cited by 131 publications

(140 citation statements)

References 9 publications

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“…In this system, in addition to the capacity to form phosphate bridges, the higher stability of 3 ,5 bonds relative to 2 ,3 bonds in double-stranded RNA structures was observed [109]. In the presence of 1-2 diamino ethane at alkaline pH the self-polymerization of 2 ,3 cyclic adenosine mono-phosphate (2 ,5 cAMP) was described [110]. The non-enzymatic ligation of short-chained 2 -5 -or 3 -5 -linked oligoribonucleotides on 2 -5 -or 3 -5 -linked complementary templates was also reported [111].…”

Section: Abiotic Rnamentioning

confidence: 81%

Formamide and the origin of life

Saladino

Crestini

Pino

et al. 2012

Physics of Life Reviews

260

234

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The complexity of life boils down to the definition: "self-sustained chemical system capable of undergoing Darwinian evolution" (Joyce, 1994) [1]. The term "self-sustained" implies a set of chemical reactions capable of harnessing energy from the environment, using it to carry out programmed anabolic and catabolic functions. We briefly present our opinion on the general validity of this definition.Running anabolic and catabolic functions entails complex chemical information whose stability, reproducibility and evolution constitute the core of what is dubbed genetics.Life as-we-know-it is made of the intimate interaction of metabolism and genetics, both built around the chemistry of the most common elements of the Universe (hydrogen, oxygen, nitrogen, carbon). Other elements like phosphorus and sulphur play important but ancillary and potentially replaceable roles.The reproducible interaction of metabolic and genetic cycles results in the hypercycles of organization and de-organization of chemical information that we consider living entities. In order to approach the problem of the origin of life it is therefore reasonable to start from the assumption that both metabolism and genetics had a common origin, shared a common chemical frame, were embedded in physical-chemical conditions favourable for the onset of both.The most abundant three-atoms organic compound in interstellar environment is hydrogen cyanide HCN, the most abundant three-atoms inorganic compound is water H 2 O. The combination of the two results in the formation of formamide H 2 NCOH. We have explored the chemistry of formamide in conditions compatible with the synthesis and the stability of compounds of potential pre-genetic and pre-metabolic interest. We discuss evidence showing (i) that all the compounds necessary for the build-up of nucleic acids are easily obtained abiotically, (ii) that essentially all the steps leading to the spontaneous generation of RNA are abiotically possible, (iii) that the key compounds of extant metabolic cycles are obtained in the same chemical frame, often in the same test tube.How close are these observations to a plausible scenario for the origin of life?

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Section: Abiotic Rnamentioning

confidence: 81%

Formamide and the origin of life

Saladino

Crestini

Pino

et al. 2012

Physics of Life Reviews

260

234

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“…concentration by evaporation, adsorption or formation of eutectic solutions. It was shown that selfpolymerization of A>p in high-concentrated solutions and in the dry state results in the formation of phosphodiester linkages with ratio of 3 ,5 /2 ,5 more than 1,5 (Verlander et al, 1973). Recently the ligation of hairpin ribozyme substrates, one of which contained 2 ,3 -cyclic phosphate, under eutectic conditions was reported.…”

Section: Catalysis Of Ligation Reaction By Divalent Metal Ionsmentioning

confidence: 99%

The nonenzymatic template-directed ligation of oligonucleotides

et al. 2006

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Abstract. The nonenzymatic template-directed ligation of oligonucleotides containing 2 ,3 -cyclic phosphate was investigated in the presence of divalent cations. Ligation of the oligonucleotides readily occurred in the presence of Mg 2+ , Mn 2+ , Co 2+ , Zn 2+ , Pb 2+ . Efficacy of the metal ion catalysts inversely correlated with pKa values of the metal-bound water molecules. The intermolecular transesterification reaction yielded at least 95% of 2 ,5 -phosphodiester bonds independently on the nature of the metal ion. Relatively high reaction yields (up to 15%) suggest, that RNA fragmentation to oligonucleotides with 2 ,3 -cyclic phosphates, followed by reactions of those oligonucleotides could provide a source of new RNA molecules under prebiotic conditions.

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“…Thew ellknown preferential hydrolysis of 2',5'-bonds in ah elical context [11,13] might have played ak ey role in this transition, with 3',5'-linkages becoming enriched simply through the depletion of 2',5'-linked material. However,r ather than just degrading RNA, am ore plausible scenario would embrace recycling, with formation of new 3',5'-bonds through repair of the broken linkages.Atheoretical model addressing this was proposed in 1977 by Usher, [14] who envisioned that day/night alternation on the early earth could have created suitable conditions for the degradation of 2',5'-bonds and subsequent joining of the resulting fragments.H owever,U sher invoked dry-state non-templated oligomerization for the joining chemistry,a nd this is known to only slightly favor the formation of natural linkages [15] and is limited by unfavorable equilibrium considerations to producing short fragments. [16] Furthermore,hydrolysis followed by non-templated synthesis would not allow the propagation of sequence information and, accordingly,w es ought as cheme whereby 2',5'-bonds could be "corrected" to 3',5'-bonds through proofreading with retention of sequence.W er easoned that any such repair process would have an energetic cost, and hence sought an energy-dissipative cycle [17,18] that would combine selective hydrolysis of duplex 2',5'-linkages with templated 3',5'-selective ligation chemistry.…”

mentioning

confidence: 99%

Non‐Enzymatic RNA Backbone Proofreading through Energy‐Dissipative Recycling

Mariani

Sutherland

2017

Angewandte Chemie

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Non-enzymatic oligomerization of activated ribonucleotides leads to ribonucleic acids that contain amixture of 2',5'-and 3',5'-linkages,and overcoming this backbone heterogeneity has long been considered am ajor limitation to the prebiotic emergence of RNA. Herein, we demonstrate nonenzymatic chemistry that progressively converts 2',5'-linkages into 3',5'-linkages through iterative degradation and repair.The energetic costs of this proofreading are met by the hydrolytic turnover of ap hosphate activating agent and an acylating agent. With multiple rounds of this energy-dissipative recycling,w es how that all-3',5'-linked duplex RNAc an emerge from ab ackbone heterogeneous mixture,t hereby delineating ar oute that could have driven RNAe volution on the early earth.

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Catalysts for the self-polymerization of adenosine cyclic 2′,3′-phosphate

Cited by 131 publications

References 9 publications

Formamide and the origin of life

Formamide and the origin of life

The nonenzymatic template-directed ligation of oligonucleotides

Non‐Enzymatic RNA Backbone Proofreading through Energy‐Dissipative Recycling

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