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Cited by 54Origins and Evolution of LifeRNA and protein synthesis mechanismsDNA and Nucleic Acid Chemistry

Synthesis of Cytidine Ribonucleotides by Stepwise Assembly of the Heterocycle on a Sugar Phosphate

Ingar, Abdul‐Aziz, Luke, Richard W. A., Hayter, Barry R., Sutherland, John D.·2003·ChemBioChem
DOI 10.1002/cbic.200300554
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Abstract

Although various syntheses of the nucleic acid bases exist and ribose is a product of the formose reaction, no prebiotically plausible methods for attaching pyrimidine bases to ribose to give nucleosides have been described. Kinetic and thermodynamic factors are thought to mitigate against such condensation reactions in aqueous solution. This inability to produce pyrimidine nucleosides and hence nucleotides is a major stumbling block of the “RNA World” hypothesis and has led to suggestions of alternative nucleic acids as evolutionary precursors to RNA. Here, we show that a process in which the base is assembled in stages on a sugar phosphate can produce cytidine nucleotides. The sequential action of cyanamide and cyanoacetylene on arabinose‐3‐phosphate produces cytidine‐2′,3′‐cyclophosphate and arabinocytidine‐3′‐phosphate.

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Crossref · 10.1002/cbic.200300554

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  • This in turn reacts with cyanoacetylene to form a tricyclic intermediate that hydrolyzes to produce a mixture of cytosine arabinoside-3'-phosphate and cytosine 2',3'-cyclic phosphate.

    “This in turn reacts with cyanoacetylene to form a tricyclic intermediate that hydrolyzes to produce a mixture of cytosine arabinoside-3 ′ -phosphate and cytosine 2 ′ ,3 ′ -cyclic phosphate.”

    From Protocells and RNA Self-Replication (2018) · cites this paper as Ingar et al. 2003

  • Starting simply with glycolaldehyde and cyanamide, in the presence of 1 M phosphate at neutral pH, gives 2-amino-oxazole in excellent yield.

    “Sutherland and colleagues (Ingar et al. 2003;Anastasi et al. 2007;Powner et al. 2009) avoided the complication of the separate synthesis of sugars by starting simply with glycolaldehyde and cyanamide, which in the presence of 1 M phosphate at neutral pH gives 2-amino-oxazole an excellent yield (Fig. 2B).”

    From Protocells and RNA Self-Replication (2018) · cites this paper as Ingar et al. 2003

  • Arabinose 3-phosphate reacts with cyanamide to give the corresponding amino-oxazoline.

    “Like arabinose, arabinose 3-phosphate reacts with cyanamide to give the corresponding amino-oxazoline (Fig. 2C).”

    From Protocells and RNA Self-Replication (2018) · cites this paper as Ingar et al. 2003

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Authors
Ingar, A., Luke, R. W. A., Hayter, B. R., & Sutherland, J. D.
Affiliations
  • University of Manchester (GB)
  • AstraZeneca (United Kingdom) (GB)
ORCID
Sutherland, John D.
Venue
ChemBioChem
Publisher
Wiley
Published
2003-06-02
Volume
4
Issue
6
Pages
504-507
ISSN
  • 1439-4227 (ISSN-L)
  • 1439-7633
DOI
10.1002/cbic.200300554
OpenAlex
W2122127862
Cited by
54
References
5
Citations by year
2026: 2 · 2025: 1 · 2024: 1 · 2023: 3 · 2022: 2 · 2020: 3 · 2019: 2 · 2018: 1 · 2017: 2 · 2016: 4 · 2015: 1 · 2014: 2 · 2013: 1 · 2012: 2
FWCI
2.50
Type
journal article
Language
en
Open access
closed
Licence
onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations
  • ChemBioChem (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
Keywords
nucleoside synthesis, prebiotic chemistry, RNA world, pyrimidine nucleosides, sugar phosphates, cyanamide, HC3N
MeSH terms
Cytidine, Magnetic Resonance Spectroscopy, Ribonucleotides, Sugar Phosphates, Molecular Structure

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