Oligomerization of activated derivatives of 3′-amino-3′-deoxyguanosine on poly(C) and poly(dC) templates

Zieliński, Wojciech; Orgel, Leslie E.

doi:10.1093/nar/13.7.2469

Cited by 52 publications

(36 citation statements)

References 10 publications

(15 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, the 2 0 -and 3 0 -hydroxyl groups of activated mononucleotides can be replaced by an amino group at either position, providing enhanced nucleophilicity and resulting in more rapid template-dependent (and template-independent) oligomerization (Lohrmann and Orgel 1976;Zielinski and Orgel 1985). Dinucleotide building blocks, consisting of 3 0 -amino, 3 0 -deoxynucleotide analogs can also be oligomerized in the presence of a suitable condensing agent (Zielinski and Orgel 1987).…”

Section: Nonenzymatic Replication Of Rnamentioning

confidence: 99%

The Origins of the RNA World

Robertson¹,

Joyce²

2010

Cold Spring Harbor Perspectives in Biology

445

326

View full text Add to dashboard Cite

SUMMARYThe general notion of an "RNA World" is that, in the early development of life on the Earth, genetic continuity was assured by the replication of RNA and genetically encoded proteins were not involved as catalysts. There is now strong evidence indicating that an RNA World did indeed exist before DNA-and protein-based life. However, arguments regarding whether life on Earth began with RNA are more tenuous. It might be imagined that all of the components of RNA were available in some prebiotic pool, and that these components assembled into replicating, evolving polynucleotides without the prior existence of any evolved macromolecules. A thorough consideration of this "RNA-first" view of the origin of life must reconcile concerns regarding the intractable mixtures that are obtained in experiments designed to simulate the chemistry of the primitive Earth. Perhaps these concerns will eventually be resolved, and recent experimental findings provide some reason for optimism. However, the problem of the origin of the RNA World is far from being solved, and it is fruitful to consider the alternative possibility that RNA was preceded by some other replicating, evolving molecule, just as DNA and proteins were preceded by RNA.

show abstract

Section: Nonenzymatic Replication Of Rnamentioning

confidence: 99%

The Origins of the RNA World

Robertson¹,

Joyce²

2010

Cold Spring Harbor Perspectives in Biology

445

326

View full text Add to dashboard Cite

show abstract

“…We describe in this paper (a) some useful modifications in methods for incorporating 5 Preparation of Dimers I and IV (Solution Phase) Compound IV was prepared in solution and converted to the hydrogen phosphonate (I) as previously described. '5 The properties for Dimer IV are: 3'P NMR (in pyridine-d5), 6 (VIIa) was taken up in anhydrous acetonitrile (6 ml) and treated with 5'-O-trityl-3'-amino-3'-deoxythymidine25 (270 mg, 0.56 mmole) in carbon tetrachloride (6 ml) and triethylamine (1 ml 4.75 (m, lH, H3'), 5.92 (m, lH, Hl'), 6.29 (t, lH, Hl'), 7.82 (s, 1H, H6), 7.85 (s, 1H, H6). Finally, the phosphoramidate salt hydrolyzed cleanly to 3'-aminodeoxythymidine (RP HPLC 9.0 min, positive ninhydrin test) and thymidine 5'-phosphate (RP HPLC 6.7 min) when treated with 80% aqueous acetic acid (16 h, room temp).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of oligonucleotides containing aminodeoxythymidine units

Gryaznov

Letsinger

1992

Nucl Acids Res

View full text Add to dashboard Cite

show abstract

“…Work from our laboratory has extended this concept to the transcription of DNA into a complementary threose nucleic acid (TNA) polymer (10)(11)(12). More generally, the formation of Watson-Crick basepaired duplexes between different nucleic acids suggests that information transfer should be possible between many different nucleic acids, including variants such as 3′-amino RNA and DNA (13)(14)(15), 2′-amino RNA and DNA (16,17), 4′-3′ lyxopyranosyl-NA (18), glycerol nucleic acid (GNA) (19), TNA (20), and others. As long as two polymers can base-pair with each other, it seems reasonable that a mixed polymer containing monomers of each type could still engage in base-pair mediated replication.…”

mentioning

confidence: 99%

Evolution of functional nucleic acids in the presence of nonheritable backbone heterogeneity

Trevino

Zhang

Elenko

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

Multiple lines of evidence support the hypothesis that the early evolution of life was dominated by RNA, which can both transfer information from generation to generation through replication directed by base-pairing, and carry out biochemical activities by folding into functional structures. To understand how life emerged from prebiotic chemistry we must therefore explain the steps that led to the emergence of the RNA world, and in particular, the synthesis of RNA. The generation of pools of highly pure ribonucleotides on the early Earth seems unlikely, but the presence of alternative nucleotides would support the assembly of nucleic acid polymers containing nonheritable backbone heterogeneity. We suggest that homogeneous monomers might not have been necessary if populations of heterogeneous nucleic acid molecules could evolve reproducible function. For such evolution to be possible, function would have to be maintained despite the repeated scrambling of backbone chemistry from generation to generation. We have tested this possibility in a simplified model system, by using a T7 RNA polymerase variant capable of transcribing nucleic acids that contain an approximately 1∶1 mixture of deoxy-and ribonucleotides. We readily isolated nucleotide-binding aptamers by utilizing an in vitro selection process that shuffles the order of deoxy-and ribonucleotides in each round. We describe two such RNA/DNA mosaic nucleic acid aptamers that specifically bind ATP and GTP, respectively. We conclude that nonheritable variations in nucleic acid backbone structure may not have posed an insurmountable barrier to the emergence of functionality in early nucleic acids.abiogenesis | genetic takeover | RNA progenitor | origin of life G iven that RNA is likely to have played a key role early in the evolution of life (1), understanding the origins of the RNAbased biosphere is a critical aspect of understanding the origin of life. The difficulties associated with the prebiotic synthesis of a macromolecule as complicated and fragile as RNA have stimulated interest in the hypothesis that RNA was preceded by simpler and/or more stable progenitor nucleic acids (2-4). The systematic exploration of nucleic acids that are structurally related to RNA has revealed that the formation of stable WatsonCrick base-paired, antiparallel duplex structures is compatible with a surprising degree of variation in the sugar-phosphate backbone (5). These studies imply that many distinct nucleic acids are in principle capable of mediating the inheritance of genetic information. On the other hand, recent advances in the prebiotic chemistry leading to the pyrimidine ribonucleotides (6) have revived the prospects of the RNA-first model, with the attendant advantage of avoiding a difficult genetic takeover. Both RNAfirst and RNA-late models assume that life began with a single, well-defined genetic polymer. Perhaps the greatest problem implicit in this assumption is the challenge of explaining the origin of pure nucleotide monomers on the early Earth. Indeed, the supp...

show abstract

Oligomerization of activated derivatives of 3′-amino-3′-deoxyguanosine on poly(C) and poly(dC) templates

Cited by 52 publications

References 10 publications

The Origins of the RNA World

The Origins of the RNA World

Synthesis and properties of oligonucleotides containing aminodeoxythymidine units

Evolution of functional nucleic acids in the presence of nonheritable backbone heterogeneity

Contact Info

Product

Resources

About