Literature DB >> 21860459

A route to enantiopure RNA precursors from nearly racemic starting materials.

Jason E Hein1, Eric Tse, Donna G Blackmond.   

Abstract

The single-handedness of biological molecules is critical for molecular recognition and replication processes and would seem to be a prerequisite for the origin of life. A drawback of recently reported synthetic routes to RNA is the requirement for enantioenriched reactants, which fails to address the puzzle of how the single chirality of biological molecules arose. Here, we report the synthesis of highly enantioenriched RNA precursor molecules from racemic starting materials, with the molecular asymmetry derived solely from a small initial imbalance of the amino-acid enantiomers present in the reaction mixture. Acting as spectators to the main reaction chemistry, the amino acids orchestrate a sequence of physical and chemical amplification processes. The emergence of molecules of single chirality from complex, multi-component mixtures supports the robustness of this synthesis process under potential prebiotic conditions and provides a plausible explanation for the single-handedness of biological molecules before the emergence of self-replicating informational polymers.

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Year:  2011        PMID: 21860459     DOI: 10.1038/nchem.1108

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  23 in total

1.  Summary and implications of reported amino acid concentrations in the Murchison meteorite

Authors:  E L Shock; M D Schulte
Journal:  Geochim Cosmochim Acta       Date:  1990-11       Impact factor: 5.010

2.  Large nonlinear effect observed in the enantiomeric excess of proline in solution and that in the solid state.

Authors:  Yujiro Hayashi; Masayoshi Matsuzawa; Junichiro Yamaguchi; Sayaka Yonehara; Yasunobu Matsumoto; Mitsuru Shoji; Daisuke Hashizume; Hiroyuki Koshino
Journal:  Angew Chem Int Ed Engl       Date:  2006-07-10       Impact factor: 15.336

3.  Thermodynamic control of asymmetric amplification in amino acid catalysis.

Authors:  Martin Klussmann; Hiroshi Iwamura; Suju P Mathew; David H Wells; Urvish Pandya; Alan Armstrong; Donna G Blackmond
Journal:  Nature       Date:  2006-06-01       Impact factor: 49.962

4.  Direct assembly of nucleoside precursors from two- and three-carbon units.

Authors:  Carole Anastasi; Michael A Crowe; Matthew W Powner; John D Sutherland
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-18       Impact factor: 15.336

5.  Emergence of solution-phase homochirality via crystal engineering of amino acids.

Authors:  Martin Klussmann; Toshiko Izumi; Andrew J P White; Alan Armstrong; Donna G Blackmond
Journal:  J Am Chem Soc       Date:  2007-05-26       Impact factor: 15.419

6.  A mechanism ffr the amplification of fluctuations in racemic mixtures.

Authors:  H J Morowitz
Journal:  J Theor Biol       Date:  1969-12       Impact factor: 2.691

7.  L-amino acids catalyze the formation of an excess of D-glyceraldehyde, and thus of other D sugars, under credible prebiotic conditions.

Authors:  Ronald Breslow; Zhan-Ling Cheng
Journal:  Proc Natl Acad Sci U S A       Date:  2010-03-15       Impact factor: 11.205

Review 8.  Expanding roles for diverse physical phenomena during the origin of life.

Authors:  Itay Budin; Jack W Szostak
Journal:  Annu Rev Biophys       Date:  2010       Impact factor: 12.981

9.  Chiral selection in poly(C)-directed synthesis of oligo(G).

Authors:  G F Joyce; G M Visser; C A van Boeckel; J H van Boom; L E Orgel; J van Westrenen
Journal:  Nature       Date:  1984 Aug 16-22       Impact factor: 49.962

10.  Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions.

Authors:  Matthew W Powner; Béatrice Gerland; John D Sutherland
Journal:  Nature       Date:  2009-05-14       Impact factor: 49.962

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  18 in total

Review 1.  The Origin of Biological Homochirality.

Authors:  Donna G Blackmond
Journal:  Cold Spring Harb Perspect Biol       Date:  2019-03-01       Impact factor: 10.005

2.  Primitive selection of the fittest emerging through functional synergy in nucleopeptide networks.

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Journal:  Proc Natl Acad Sci U S A       Date:  2021-03-02       Impact factor: 11.205

3.  Chiral encoding may provide a simple solution to the origin of life.

Authors:  Ashley Brewer; Anthony P Davis
Journal:  Nat Chem       Date:  2014-07       Impact factor: 24.427

4.  How DNA and RNA subunits might have formed to make the first genetic alphabet.

Authors:  Kristian Le Vay; Hannes Mutschler
Journal:  Nature       Date:  2020-06       Impact factor: 49.962

Review 5.  On the Origin of Sugar Handedness: Facts, Hypotheses and Missing Links-A Review.

Authors:  R Fernando Martínez; Louis A Cuccia; Cristóbal Viedma; Pedro Cintas
Journal:  Orig Life Evol Biosph       Date:  2022-07-07       Impact factor: 1.120

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

Authors:  Ronald Breslow; Vijayakumar Ramalingam; Chandrakumar Appayee
Journal:  Orig Life Evol Biosph       Date:  2013-12-18       Impact factor: 1.950

7.  Harnessing chemical energy for the activation and joining of prebiotic building blocks.

Authors:  Ziwei Liu; Long-Fei Wu; Jianfeng Xu; Claudia Bonfio; David A Russell; John D Sutherland
Journal:  Nat Chem       Date:  2020-10-22       Impact factor: 24.427

8.  Unusually high α-proton acidity of prolyl residues in cyclic peptides.

Authors:  Oliver R Maguire; Bethany Taylor; Eleanor M Higgins; Matthew Rees; Steven L Cobb; Nigel S Simpkins; Christopher J Hayes; AnnMarie C O'Donoghue
Journal:  Chem Sci       Date:  2020-07-02       Impact factor: 9.825

Review 9.  Illuminating Life's Origins: UV Photochemistry in Abiotic Synthesis of Biomolecules.

Authors:  Nicholas J Green; Jianfeng Xu; John D Sutherland
Journal:  J Am Chem Soc       Date:  2021-04-21       Impact factor: 15.419

10.  Multicomponent assembly of proposed DNA precursors in water.

Authors:  Matthew W Powner; Shao-Liang Zheng; Jack W Szostak
Journal:  J Am Chem Soc       Date:  2012-08-09       Impact factor: 15.419

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