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Issue 75, 2017
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Prebiotic synthesis of 2-deoxy-D-ribose from interstellar building blocks promoted by amino esters or amino nitriles

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Abstract

Understanding the prebiotic genesis of 2-deoxy-D-ribose, which forms the backbone of DNA, is of crucial importance to unravelling the origins of life, yet remains open to debate. Here we demonstrate that 20 mol% of proteinogenic amino esters promote the selective formation of 2-deoxy-D-ribose over 2-deoxy-D-threopentose in combined yields of ≥4%. We also demonstrate the first aldol reaction promoted by prebiotically-relevant proteinogenic amino nitriles (20 mol%) for the enantioselective synthesis of D-glyceraldehyde with 6% ee, and its subsequent conversion into 2-deoxy-D-ribose in yields of ≥ 5%. Finally, we explore the combination of these two steps in a one-pot process using 20 mol% of an amino ester or amino nitrile promoter. It is hence demonstrated that three interstellar starting materials, when mixed together with an appropriate promoter, can directly lead to the formation of a mixture of higher carbohydrates, including 2-deoxy-D-ribose.

Graphical abstract: Prebiotic synthesis of 2-deoxy-d-ribose from interstellar building blocks promoted by amino esters or amino nitriles

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Publication details

The article was received on 03 Aug 2017, accepted on 01 Sep 2017 and first published on 08 Sep 2017


Article type: Communication
DOI: 10.1039/C7CC06083A
Citation: Chem. Commun., 2017,53, 10362-10365
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    Prebiotic synthesis of 2-deoxy-D-ribose from interstellar building blocks promoted by amino esters or amino nitriles

    A. M. Steer, N. Bia, D. K. Smith and P. A. Clarke, Chem. Commun., 2017, 53, 10362
    DOI: 10.1039/C7CC06083A

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