Synthesis and base-pairing properties of pyrazine nucleic acids. (2nd June 2020)
- Record Type:
- Journal Article
- Title:
- Synthesis and base-pairing properties of pyrazine nucleic acids. (2nd June 2020)
- Main Title:
- Synthesis and base-pairing properties of pyrazine nucleic acids
- Authors:
- Gately, Maura
Wong, Sarah
Peoples, Jennifer
Galamay, Davin
Delgado, Guillermo
Weber, Arthur L.
Campbell, Tammy - Abstract:
- Abstract: The diversity of backbone modifications in the study of primitive informational polymers is partly limited by the plausible formation of their prebiotic starting components. In this paper, we synthesize pyrazine nucleic acid, an acyclic polymer, with the nucleoside derivable from a prebiotic one-pot synthesis containing alanine amide and D -ribose. Pyrazine nucleic acid (PzNA) which has a backbone structurally similar to glycerol nucleic acid (GNA), contain pyrazine derived nucleosides as informational elements that may exhibit base pairing properties similar to the pyrimidines present in RNA. [ 1 ] We found that insertion of pyrazinone nucleotides into DNA oligonucleotide sequences is not well-tolerated, and that homogenous sequences of PzNA are unable to form duplexes with RNA or DNA. Reasons for our results may be attributed to the pyrazine-2-one moiety, which is purposed to be a thymine analog, but has a lower p K a (p K a ∼ 8.5) than thymine and uracil. Additionally, we discovered an "apparent" regioselective protection of pyrazine-2-one derivatives in the presence of a secondary hydroxyl group that proved crucial in the preparation of the pyrazine-2-one phosphoramidite. The regioselectivity observed is proposed to be of general interest in the context of heterocyclic chemistry. In the larger context of origins of life studies, it points to the importance of keto-enol preferences of the canonical nucleobases versus pyrazine heterocycles in functioning asAbstract: The diversity of backbone modifications in the study of primitive informational polymers is partly limited by the plausible formation of their prebiotic starting components. In this paper, we synthesize pyrazine nucleic acid, an acyclic polymer, with the nucleoside derivable from a prebiotic one-pot synthesis containing alanine amide and D -ribose. Pyrazine nucleic acid (PzNA) which has a backbone structurally similar to glycerol nucleic acid (GNA), contain pyrazine derived nucleosides as informational elements that may exhibit base pairing properties similar to the pyrimidines present in RNA. [ 1 ] We found that insertion of pyrazinone nucleotides into DNA oligonucleotide sequences is not well-tolerated, and that homogenous sequences of PzNA are unable to form duplexes with RNA or DNA. Reasons for our results may be attributed to the pyrazine-2-one moiety, which is purposed to be a thymine analog, but has a lower p K a (p K a ∼ 8.5) than thymine and uracil. Additionally, we discovered an "apparent" regioselective protection of pyrazine-2-one derivatives in the presence of a secondary hydroxyl group that proved crucial in the preparation of the pyrazine-2-one phosphoramidite. The regioselectivity observed is proposed to be of general interest in the context of heterocyclic chemistry. In the larger context of origins of life studies, it points to the importance of keto-enol preferences of the canonical nucleobases versus pyrazine heterocycles in functioning as recognition elements. … (more)
- Is Part Of:
- Nucleosides, nucleotides & nucleic acids. Volume 39:Number 6(2020)
- Journal:
- Nucleosides, nucleotides & nucleic acids
- Issue:
- Volume 39:Number 6(2020)
- Issue Display:
- Volume 39, Issue 6 (2020)
- Year:
- 2020
- Volume:
- 39
- Issue:
- 6
- Issue Sort Value:
- 2020-0039-0006-0000
- Page Start:
- 866
- Page End:
- 891
- Publication Date:
- 2020-06-02
- Subjects:
- nucleosides -- nucleic acids -- pyrazinone -- origins of life -- prebiotic
Nucleosides -- Periodicals
Nucleotides -- Periodicals
Nucleic acids -- Periodicals
572.8 - Journal URLs:
- http://www.tandfonline.com/toc/lncn20/current ↗
http://www.tandfonline.com/ ↗ - DOI:
- 10.1080/15257770.2020.1711525 ↗
- Languages:
- English
- ISSNs:
- 1525-7770
- Deposit Type:
- Legaldeposit
- View Content:
- Available online (eLD content is only available in our Reading Rooms) ↗
- Physical Locations:
- British Library DSC - 6184.092000
British Library DSC - BLDSS-3PM
British Library HMNTS - ELD Digital store - Ingest File:
- 13622.xml