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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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JournalChemical Communications
DateAccepted/In press - 1 Sep 2017
DateE-pub ahead of print - 8 Sep 2017
DatePublished (current) - 25 Sep 2017
Volume53
Number of pages4
Pages (from-to)10362-10365
Early online date8/09/17
Original languageEnglish

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 %e.e., 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

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© 2017, The Royal Society of Chemistry. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

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