Literature DB >> 19478058

On the origin of terrestrial homochirality for nucleosides and amino acids.

Ronald Breslow1, Zhan-Ling Cheng.   

Abstract

Before life could start on earth, it was important that the amino acid building blocks be present in a predominant handedness called the L configuration and that the ribose of RNA be predominantly in the D configuration. Because ordinary chemical processes would produce them in equal L and D amounts, it has long been a puzzle how the needed selectivities could have arisen. Carbonaceous chondrites such as the Murchison meteorite, which landed in Australia in 1969, brought some unusual amino acids with a methyl group replacing their alpha hydrogen. They cannot racemize and have a small but real excess of those with the L configuration. We have shown that they can partake in a synthesis of normal L amino acids under credible prebiotic conditions. We and others showed that small preferences can be amplified into solutions with very high dominance of the L amino acids because of the higher solubility of the pure L form than of the more stable DL racemic compound crystal. Here, we show that such solubility-based amplification of small excesses of three D nucleosides, uridine, adenosine, and cytidine, can also occur to form solutions with very high D dominance under credible prebiotic conditions. Guanosine crystallizes as a conglomerate and does not amplify in this way. However, under prebiotic conditions it could have been formed from homochiral D ribose from the hydrolysis of amplified adenosine or cytidine.

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Year:  2009        PMID: 19478058      PMCID: PMC2695116          DOI: 10.1073/pnas.0904350106

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  14 in total

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2.  The extraterrestrial origin of the homochirality of biomolecules--rebuttal to a critique.

Authors:  W A Bonner; J M Greenberg; E Rubenstein
Journal:  Orig Life Evol Biosph       Date:  1999-03       Impact factor: 1.950

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Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

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Journal:  Org Lett       Date:  2008-05-21       Impact factor: 6.005

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

Authors:  H J Morowitz
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8.  The sugar model: catalysis by amines and amino acid products.

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Journal:  Orig Life Evol Biosph       Date:  2001 Feb-Apr       Impact factor: 1.950

9.  Enantiomeric excesses in meteoritic amino acids.

Authors:  J R Cronin; S Pizzarello
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Review 3.  The role of natural selection in the origin of life.

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Journal:  Proc Natl Acad Sci U S A       Date:  2015-04-13       Impact factor: 11.205

5.  Enantiomeric excesses in the Murchison meteorite and the origin of homochirality in terrestrial biology.

Authors:  Jeffrey L Bada
Journal:  Proc Natl Acad Sci U S A       Date:  2009-07-30       Impact factor: 11.205

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

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Review 7.  The Origin of Biological Homochirality.

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8.  A Broad Substrate Scope of Aza-Friedel-Crafts Alkylation for the Synthesis of Quaternary α-Amino Esters.

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9.  Spontaneous Resolution and Super-coiling in Xerogels of the Products of Photo-Induced Formose Reaction.

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Journal:  Orig Life Evol Biosph       Date:  2019-10-22       Impact factor: 1.950

10.  Transketolase reaction under credible prebiotic conditions.

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Journal:  Proc Natl Acad Sci U S A       Date:  2013-02-25       Impact factor: 11.205

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