Catalysis of glyceraldehyde synthesis by primary or secondary amino acids under prebiotic conditions as a function of pH

Origins of Life and Evolution of the Biosphere : the Journal of the International Society for the Study of the Origin of Life
Ronald BreslowChandrakumar Appayee

Abstract

The synthesis of an excess of D-glyceraldehyde by coupling glycolaldehyde with formaldehyde under prebiotic conditions is catalyzed by L amino acids having primary amino groups at acidic pH's, but at neutral or higher pH's they preferentially form L-glyceraldehyde. L Amino acids having secondary amino groups, such as proline, have the reverse preferences, affording excess L-glyceraldehyde at low pH but excess D-glyceraldehyde at higher pHs. Detailed mechanistic proposals make these preferences understandable. The relevance of these findings to the origin of D sugars on prebiotic Earth is described.

References

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Jun 2, 2006·Nature·Martin KlussmannDonna G Blackmond
Aug 30, 2006·Proceedings of the National Academy of Sciences of the United States of America·Ronald Breslow, Mindy S Levine
May 29, 2007·Journal of the American Chemical Society·Martin KlussmannDonna G Blackmond
Nov 17, 2009·Origins of Life and Evolution of the Biosphere : the Journal of the International Society for the Study of the Origin of Life·Ronald BreslowZhan-Ling Cheng
Mar 17, 2010·Proceedings of the National Academy of Sciences of the United States of America·Ronald Breslow, Zhan-Ling Cheng
May 15, 2010·Journal of the American Chemical Society·Donna G BlackmondAlan Armstrong
Aug 24, 2011·Nature Chemistry·Jason E HeinDonna G Blackmond
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Feb 27, 2013·Proceedings of the National Academy of Sciences of the United States of America·Ronald Breslow, Chandrakumar Appayee

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Citations

Mar 1, 2014·Journal of the American Chemical Society·Chandrakumar Appayee, Ronald Breslow
Oct 13, 2016·Faraday Discussions·Jonny ProppeMarkus Reiher
Mar 26, 2015·Chemical Communications : Chem Comm·Arkadii V TarasevychJean-Claude Guillemin
Jan 31, 2019·Astrobiology·Hyo-Joong Kim, Justin Kim
Jan 16, 2018·Chemical Communications : Chem Comm·Zoe R ToddDimitar D Sasselov
Jun 8, 2021·Chemical Science·Oliver R MaguireAnnMarie C O'Donoghue
May 5, 2017·ACS Central Science·Alexander J WagnerDonna G Blackmond
Nov 20, 2019·Chemical Reviews·Daniel P GlavinJason P Dworkin

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