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Prebiotic synthesis of simple sugars by photoredox systems chemistry
Open accessAbstract
A recent synthesis of activated pyrimidine ribonucleotides under prebiotically plausible conditions relied on mixed oxygenous and nitrogenous systems chemistry. As it stands, this synthesis provides support for the involvement of RNA in the origin of life, but such support would be considerably strengthened if the sugar building blocks for the synthesis--glycolaldehyde and glyceraldehyde--could be shown to derive from one carbon feedstock molecules using similarly mixed oxygenous and nitrogenous systems chemistry. Here, we show that these sugars can be formed from hydrogen cyanide by ultraviolet irradiation in the presence of cyanometallates in a remarkable systems chemistry process. Using copper cyanide complexes, the process operates catalytically to disproportionate hydrogen cyanide, first generating the sugars and then sequestering them as simple derivatives.
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In the citing paper
“in 2012, Ritson and Sutherland [26] revealed a more continuous reaction network starting from HCN 1 that produces glycolaldehyde 4 and glyceraldehyde 5 in a chemical process driven by UV-photocatalytic irradiation of cyanocuprate complexes”
From Prebiotic Reaction Networks in Water (2020) · cites this paper as [26]
In the citing paper
“The production of these hydroxyaldehydes follows a Kiliani-Fischer homologation mechanism that occurs within a single aqueous mixture.”
From Prebiotic Reaction Networks in Water (2020) · cites this paper as [26]
In the citing paper
“irradiation of the cyanocuprates photooxidises the copper(I) centres to copper(II) generating in the process a hydrated electron (eaq−), which effectively serves as a reducing agent.”
From Prebiotic Reaction Networks in Water (2020) · cites this paper as [26]
In the citing paper
“Spontaneous hydrolysis of cyanogen yields cyanate, which reacts irreversibly, however, with both glycolaldehyde and glyceraldehyde to form oxazolidinone rings.”
From Prebiotic Reaction Networks in Water (2020) · cites this paper as [26]
In the citing paper
“Reversible addition of HCN to formaldehyde yields the cyanohydrin glycolonitrile 33, which like HCN 1 can also undergo reduction affording the imine that yields glycolaldehyde 4 after hydrolysis.”
From Prebiotic Reaction Networks in Water (2020) · cites this paper as [26]
In the citing paper
“Methanimine is subsequently hydrolysed by water to form formaldehyde 3, releasing an equivalent of ammonia.”
From Prebiotic Reaction Networks in Water (2020) · cites this paper as [26]
In the citing paper
“Another round of this homologation chemistry yields a racemic mixture of glyceraldehyde 5.”
From Prebiotic Reaction Networks in Water (2020) · cites this paper as [26]
In the citing paper
“The HCN 1 in solution is then reduced to methanimine 32, likely proceeding through a methaniminyl radical intermediate.”
From Prebiotic Reaction Networks in Water (2020) · cites this paper as [26]
In the citing paper
“Meanwhile, the copper(II) complexes oxidise HCN to cyanogen thereby restoring the initial copper(I) state.”
From Prebiotic Reaction Networks in Water (2020) · cites this paper as [26]
In the citing paper
“In the proposed mechanism, gamma radiolysis generates hydrated electrons which initiate a Kiliani-Fischer-type [26] synthesis that affords the production of the cyanohydrins, glycolonitrile and glyceronitrile 37, from the reversible addition of HCN 1 to formaldehyde 3 and glycolaldehyde, respectively.”
From Prebiotic Reaction Networks in Water (2020) · cites this paper as [26]
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Metadata
- Authors
- Ritson, D., & Sutherland, J. D.
- Affiliations
- MRC Laboratory of Molecular Biology (GB)
- Corresponding author
- Sutherland, John D.
- Venue
- Nature Chemistry
- Published
- 2012-09-30
- Volume
- 4
- Issue
- 11
- Pages
- 895-899
- ISSN
- 1755-4330 (ISSN-L)
- 1755-4349
- PMC
- PMC3589744
- OpenAlex
- W2040480490
- Cited by
- 258
- References
- 39
- Citations by year
- 2026: 20 · 2025: 17 · 2024: 19 · 2023: 18 · 2022: 29 · 2021: 16 · 2020: 26 · 2019: 21 · 2018: 21 · 2017: 23 · 2016: 13 · 2015: 13 · 2014: 12 · 2013: 10
- FWCI
- 6.12
- Type
- journal article
- Language
- en
- Open access
- green
- europepmc.org
- Licence
- www.springer.com/tdm (tdm)
- Locations
- Nature Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Europe PMC (PubMed Central) (acceptedVersion)
- PubMed Central (acceptedVersion)
- Funders
- Engineering and Physical Sciences Research Council (EP/H044140/1)
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Radical Photochemical Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Carbohydrate Chemistry and Synthesis
- Keywords
- prebiotic synthesis, monosaccharides, glycolaldehyde, glyceraldehyde, hydrogen cyanide, photoredox catalysis, copper cyanide complexes, cyanocuprates, cyanide complexes, origin of life, RNA, one-carbon feedstocks, UV irradiation
- MeSH terms
- Carbohydrates, Hydrogen Cyanide, Oxidation-Reduction, Photochemical Processes, Prebiotics, Chemistry Techniques, Synthetic
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