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. 2013 May 27;52(22):5845-7.
doi: 10.1002/anie.201300321. Epub 2013 Apr 22.

Synthesis of aldehydic ribonucleotide and amino acid precursors by photoredox chemistry

Dougal J Ritson  1 , John D Sutherland
Affiliations
Free PMC article

Synthesis of aldehydic ribonucleotide and amino acid precursors by photoredox chemistry

Dougal J Ritson et al. Angew Chem Int Ed Engl. .
Free PMC article
No abstract available

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Figures

Scheme 1
Scheme 1
Photoredox systems chemistry of hydrogen cyanide 1, with 1 also acting as the ultimate reductant.
Figure 1
Figure 1
13C NMR spectrum of the products of irradiation (2 h, pH 7) of a system made by mixing a solution of [13C2]-labeled glycolonitrile 5 (10 mm), hydrogen sulfide 10 (30 mm), and sodium phosphate (33 mm) with solid copper(I) cyanide (10 mol % with respect to 5).
Scheme 2
Scheme 2
Photoredox systems chemistry of glycolonitrile 5, with hydrogen sulfide 10 as the ultimate reductant.
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References

    1. Ritson D, Sutherland JD. Nat. Chem. 2012;4:895–899. - PMC - PubMed
    1. Powner MW, Gerland B, Sutherland JD. Nature. 2009;459:239–242. - PubMed
    1. Zahnle K, Schaefer L, Fegley B. Cold Spring Harbor Perspect. Biol. 2010;2:a004895. - PMC - PubMed
    2. Sugita S, Schultz PH. Geophys. Res. Lett. 2009;36
    1. Cleaves HJ., II Precambrian Res. 2008;164:111–118.
    1. After 6 h irradiation, the system had simplified, and acetaldehyde 1241215454561112 and formaldehyde were the predominant products. The apparent yield of at this point was 15 % (as measured by H NMR integration relative to an added standard of pentaerythritol) based on starting glycolonitrile. The production of also consumes but the amount of could not be quantitated by integration owing to overlap with the HOD signal. We did not quantitate products by another method because the system generates multiple biomolecule precursors, so the yield of any particular product has less significance than it does in conventional synthetic chemistry, it being unclear what the ideal product distribution should be: the compositional ratio of changes from 14:41:8:37 after 2 h to 0:15:10:75 after 4 h, and 0:0:12:88 after 6 h.

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