Formation of Potentially Prebiotic Amphiphiles by Reaction of β‐Hydroxy‐<i>n</i>‐alkylamines with Cyclotriphosphate

Mullen, Lee; Sutherland, John D.

doi:10.1002/ange.200700394

“…In reducing atmospheres these oxidants are also accompanied by an appreciable flux of reducing agents like formaldehyde; however, our experiments have shown no significant impediment to the accumulation of condensed phosphates. [9] We estimate that the global production of polyphosphates exceeded 10 9 mole per year under a neutral atmosphere (Figure 2), producing condensed phosphates for up to a billion years of earths history and affording steady-state concentrations in the range 10 À8 -10 À5 m in the mixed zone of the ocean, with localized concentrations across the surface of the earth in excess of 10 À3 m. [9] These concentrations are high enough to promote the phosphorylation of glycolaldehyde and b-hydroxy n-alkyl amines [13] and are comparable to modern cellular phosphorus concentrations.…”

Section: àmentioning

confidence: 99%

Production of Potentially Prebiotic Condensed Phosphates by Phosphorus Redox Chemistry

Pasek

¹

,

Kee

²

,

Bryant

³

et al. 2008

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Experimental SectionFenton Chemistry: A series of solutions were prepared with Na 2 HPO 3 or NaH 2 PO 2 in concentrations between 0.001 M to 0.1 M, iron (as FeCl 2 × 4H 2 O or as FeSO 4 ) concentrations between 0.001 M to 0.1 M, and H 2 O 2 concentrations between 0.002 M to 0.5 M (Table S1), each with a starting pH of 7±1, unless otherwise noted. Peroxide was added last to promote the reactions. One experiment was performed with a formaldehyde concentration of 1.2 M to act as a reductant. The solutions were stirred for 1-20 days, a 2 mL aliquot of each solution was extracted and placed in 2 mL of a 1:1 mixture of 10 M NaOH solution and D 2 O to quench the reaction, precipitate Fe III and prepare the sample for analysis by NMR. Decanted samples were analyzed using 31 P NMR on a Varian 300 four-nucleus probe FT-NMR spectrometer at 121.43 MHz and 24.5 ºC for 256 to 6000 scans following prior work [6a,c]

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Production of Potentially Prebiotic Condensed Phosphates by Phosphorus Redox Chemistry

Pasek

¹

,

Kee

²

,

Bryant

³

et al. 2008

View full text Add to dashboard Cite

Experimental SectionFenton Chemistry: A series of solutions were prepared with Na 2 HPO 3 or NaH 2 PO 2 in concentrations between 0.001 M to 0.1 M, iron (as FeCl 2 × 4H 2 O or as FeSO 4 ) concentrations between 0.001 M to 0.1 M, and H 2 O 2 concentrations between 0.002 M to 0.5 M (Table S1), each with a starting pH of 7±1, unless otherwise noted. Peroxide was added last to promote the reactions. One experiment was performed with a formaldehyde concentration of 1.2 M to act as a reductant. The solutions were stirred for 1-20 days, a 2 mL aliquot of each solution was extracted and placed in 2 mL of a 1:1 mixture of 10 M NaOH solution and D 2 O to quench the reaction, precipitate Fe III and prepare the sample for analysis by NMR. Decanted samples were analyzed using 31 P NMR on a Varian 300 four-nucleus probe FT-NMR spectrometer at 121.43 MHz and 24.5 ºC for 256 to 6000 scans following prior work [6a,c]

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Stabilization of Short Oligonucleotides in the Prebiotic Mix: The Potential Role of Amino Alcohols

Pino

¹

,

Mauro

²

,

Costanzo

³

et al. 2019

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Alkylation of RNA oligonucleotides by the amino alcohols 2‐amino‐2‐hydroxymethyl‐propane‐1,3‐diol (commonly known as Tris‐base) and 2‐amino‐2‐methyl‐1‐propanol has been observed in strongly acidic environments. The reaction occurs according to a carbocationic mechanism and is time‐, temperature‐, concentration‐ and, strictly, pH‐dependent. Our results suggest that amino alcohols present in the prebiotic mix could not only alter the chemical composition of the oligonucleotides formed on dry land under hydrothermal conditions, but, more importantly, they could protect the first informational polymers from degradation.

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Formation of Potentially Prebiotic Amphiphiles by Reaction of β‐Hydroxy‐n‐alkylamines with Cyclotriphosphate

Cited by 4 publications

References 16 publications

Production of Potentially Prebiotic Condensed Phosphates by Phosphorus Redox Chemistry

Production of Potentially Prebiotic Condensed Phosphates by Phosphorus Redox Chemistry

Production of Potentially Prebiotic Condensed Phosphates by Phosphorus Redox Chemistry

Stabilization of Short Oligonucleotides in the Prebiotic Mix: The Potential Role of Amino Alcohols

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