Template switching between PNA and RNA oligonucleotides

Böhler, Christof; Nielsen, Peter E.; Orgel, Leslie E.

doi:10.1038/376578a0

Cited by 244 publications

(140 citation statements)

References 11 publications

Supporting

Mentioning

119

Contrasting

Unclassified

Order By: Relevance

“…In recent years, oligonucleotide systems with properties resembling RNA have been studied intensively (22,23), and interesting candidates for a potential predecessor to RNA were found (24). Among these candidates, a peptide nucleic acid (PNA) molecule is an uncharged analogue of a standard nucleic acid, in which the sugar-phosphate backbone is replaced by a backbone held together by amide bonds (25)(26)(27)(28)(29)(30)(31)(32)(33)(34). The backbone can either be composed of N-(2-aminoethyl)glycine (aeg) or its structural analog, leading to aegPNA molecules, or of diamino acids (da), leading to daPNA structures (Fig.…”

Section: Resultsmentioning

confidence: 99%

Identification of diamino acids in the Murchison meteorite

Meierhenrich

Muñoz

Bredehöft

et al. 2004

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

190

137

View full text Add to dashboard Cite

C hondritic meteorites, in particular the CM-type carbonaceous chondrites, make up a unique subset of primitive meteorites, which are of particular interest in the context of origins of life because of their relatively high carbon content and because most of this carbon is present as organic matter. This material is a diverse mixture of compounds that in particular includes carboxylic acids, dicarboxylic acids, hydroxy acids, sulfonic acids, phosphonic acids, and amino acids in the form of monoamino alkanoic acids and monoamino alkandioic acids (1). Among these classes of compounds, a very small fraction of the meteoritic isomers is believed to support prebiotic evolutionary processes. We analyzed hydrolyzed hot-water extracts of a fresh sample of the Murchison CM-chondrite by GC-MS with a chiral column. With an efficient derivatization method and an improved detection technique we focused on compounds with more than two functional groups. MethodsA 1.19-g sample (MPI 320͞14) was taken from the interior of the Murchison meteorite by using a stone crusher. The sample provided fresh fracture surfaces. The sample was powdered for 2 ϫ 2 min at 600 rpm by a planetary micro mill (Pulverisette 7, Fritsch, Idar-Oberstein, Germany) in a positive-pressure ''class 100'' clean room. A 5-mg aliquot of the sample was imaged by a raster electron microscope (CS44, CamScan, Cranberry Township, PA), showing a homogeneous particle size distribution in the low micrometer range. A cold-water (water for organic trace analysis, Fluka) extraction was performed with a 130-mg aliquot that was subjected to diamino acid analysis. In parallel, 347 mg of the powdered sample was extracted with 700 l of water for 20 h at 100°C. After centrifugation (Eppendorf safe-lock tubes in Biopur-quality), the liquid phase was split. One hundred microliters was taken for direct derivatization by using the procedure described ref.2, leading to N,NЈ-diethoxycarbonyl diamino acid ethyl ester (ECEE) derivatives. Another aliquot of 100 l was hydrolyzed in 6 M HCl (hydrochloric acid for amino acid analysis, ampoule, Fluka) at 110°C for 24 h (3). After evaporation of the 6 M HCl, the residue was dissolved in 0.1 M HCl and derivatized by the above protocol. The ECEE derivatives obtained in this way were subjected to enantioselective GC-MS (Varian Chrompack Chirasil-L-Val capillary column; 12 m ϫ 0.25-mm inner diameter, 0.12-m film thickness, 250°C inlet temperature, pulsed splitless injection, 1.5 ml⅐min Ϫ1 constant f low of He carrier gas). The oven temperature program applied for the solvent trapping mode started at 50°C with 10°C⅐min Ϫ1 up to 90°C and then with 2°C⅐min Ϫ1 to 110°C, then was 10°C⅐min Ϫ1 to 180°C, where it was held constant for 39 min. The Agilent 6890͞5973 GC-MSD system was used. The identities of the diamino acid peaks obtained via enantioselective GC-MS were verified by comparing the retention times and the mass spectra with literature data (4) and external standards purchased from Fluka. A serpentine sample was taken as a blank (5). Results a...

show abstract

Section: Resultsmentioning

confidence: 99%

Identification of diamino acids in the Murchison meteorite

Meierhenrich

Muñoz

Bredehöft

et al. 2004

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

190

137

View full text Add to dashboard Cite

show abstract

“…The next difficulty with this hypothesis is the need of a subsequent process that would have converted the amino acid sequences into genetic information. An alternative would be the existence of a first set of residues capable of carrying information such as Peptide Nucleic Acids involving a peptide-like backbone and nucleic bases on the side chains (Bohler et al, 1995;Nielsen, 1999;Nelson et al, 2000). In this way, peptides could have played both the role of information carriers and of catalysts in a pre-RNA world (Figure 5.2).…”

Section: Catalytic Activity and Information Storagementioning

confidence: 99%

5. Prebiotic Chemistry – Biochemistry – Emergence of Life (4.4–2 Ga)

et al. 2006

View full text Add to dashboard Cite

Abstract. This chapter is devoted to a discussion about the difficulties and even the impossibility to date the events that occurred during the transition from non-living matter to the first living cells. Nevertheless, the attempts to devise plausible scenarios accounting for the emergence of the main molecular devices and processes found in biology are presented including the role of nucleotides at early stages (RNA world). On the other hand, hypotheses on the development of early metabolisms, comEarth, Moon, and Planets (2006) 98: 153-203 Ó Springer 2006

show abstract

“…Nucleic acid templated syntheses prior to the current decade predominantly used DNA or RNA templates to mediate ligation reactions that generate oligomers of DNA, RNA or structural analogues of nucleic acids [1][2][3][4][5][6]. In addition to analogues of the phosphoribose backbone, products that mimic the structure of stacked nucleic acid aromatic bases have also been generated by DNA-templated synthesis [7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Replication of cyclobutane pyrimidine dimer analogue by Ex Taq DNA polymerase

Ogino

Okamura

Fujimoto

2007

Science and Technology of Advanced Materials

View full text Add to dashboard Cite

We previously reported an efficient and reversible template-directed photoligation using 5-carboxyvinyl-2 0 -deoxyuridine ( CV U)-containing ODN at the 5 0 -terminal. This method forms d(T-CV U) as a cyclobutane pyrimidine dimer (CPD) analogue between the 3 0 -terminal thymidine and the 5 0 -terminal CV U of two oligodeoxynucleotides (ODNs). In this study, we performed PCR using a DNA template containing d(T-CV U). Then, we found that two adenines were incorporated opposite the d(T-CV U). r

show abstract

Template switching between PNA and RNA oligonucleotides

Cited by 244 publications

References 11 publications

Identification of diamino acids in the Murchison meteorite

Identification of diamino acids in the Murchison meteorite

5. Prebiotic Chemistry – Biochemistry – Emergence of Life (4.4–2 Ga)

Replication of cyclobutane pyrimidine dimer analogue by Ex Taq DNA polymerase

Contact Info

Product

Resources

About