Prebiotic Synthesis of 2-Deoxy-D-Ribose from Interstellar Building Blocks Promoted by Amino Esters or Amino Nitriles

TY - JOUR

T1 - Prebiotic Synthesis of 2-Deoxy-D-Ribose from Interstellar Building Blocks Promoted by Amino Esters or Amino Nitriles

AU - Clarke, Paul Andrew

AU - Smith, David Kelham

AU - Steer, Andrew Mark

AU - Bia, Nicolas

N1 - © 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.

PY - 2017/9/25

Y1 - 2017/9/25

N2 - 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

AB - 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

U2 - 10.1039/C7CC06083A

DO - 10.1039/C7CC06083A

M3 - Article

SN - 1359-7345

VL - 53

SP - 10362

EP - 10365

JO - Chemical Communications

JF - Chemical Communications

M1 - c7cc06083a

ER -