Literature DB >> 24575857

Deuterium studies reveal a new mechanism for the formose reaction involving hydride shifts.

Chandrakumar Appayee1, Ronald Breslow.   

Abstract

In the formose reaction, formaldehyde is converted to glycolaldehyde, its dimer, under credible prebiotic conditions. Breslow proposed a mechanism for the process in 1959, but recent studies by Benner showed that it was wrong in detail. Our present studies clarify the mechanism, which involves the original Breslow intermediates but some different connecting steps.

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Year:  2014        PMID: 24575857     DOI: 10.1021/ja410886c

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  10 in total

1.  Meteorite-catalyzed syntheses of nucleosides and of other prebiotic compounds from formamide under proton irradiation.

Authors:  Raffaele Saladino; Eleonora Carota; Giorgia Botta; Mikhail Kapralov; Gennady N Timoshenko; Alexei Y Rozanov; Eugene Krasavin; Ernesto Di Mauro
Journal:  Proc Natl Acad Sci U S A       Date:  2015-04-13       Impact factor: 11.205

2.  Evidence for tunneling in base-catalyzed isomerization of glyceraldehyde to dihydroxyacetone by hydride shift under formose conditions.

Authors:  Liang Cheng; Charles Doubleday; Ronald Breslow
Journal:  Proc Natl Acad Sci U S A       Date:  2015-03-23       Impact factor: 11.205

Review 3.  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

4.  Has Inositol Played Any Role in the Origin of Life?

Authors:  Adolfo Saiardi
Journal:  Life (Basel)       Date:  2017-06-05

5.  Hydroxymethanesulfonate from Volcanic Sulfur Dioxide: A "Mineral" Reservoir for Formaldehyde and Other Simple Carbohydrates in Prebiotic Chemistry.

Authors:  J Kawai; D Chris McLendon; H-J Kim; S A Benner
Journal:  Astrobiology       Date:  2019-01-07       Impact factor: 4.335

6.  Prebiotic Chemistry that Could Not Not Have Happened.

Authors:  Steven A Benner; Hyo-Joong Kim; Elisa Biondi
Journal:  Life (Basel)       Date:  2019-11-14

7.  Unusually large deuterium discrimination during spore photoproduct formation.

Authors:  David M Ames; Gengjie Lin; Yajun Jian; Jean Cadet; Lei Li
Journal:  J Org Chem       Date:  2014-05-15       Impact factor: 4.354

8.  The Role of Mg(OH)2 in the So-Called "Base-Free" Oxidation of Glycerol with AuPd Catalysts.

Authors:  Jile Fu; Qian He; Peter J Miedziak; Gemma L Brett; Xiaoyang Huang; Samuel Pattisson; Mark Douthwaite; Graham J Hutchings
Journal:  Chemistry       Date:  2018-01-24       Impact factor: 5.236

9.  The Messy Alkaline Formose Reaction and Its Link to Metabolism.

Authors:  Arthur Omran; Cesar Menor-Salvan; Greg Springsteen; Matthew Pasek
Journal:  Life (Basel)       Date:  2020-07-28

Review 10.  Coenzymes and Their Role in the Evolution of Life.

Authors:  Andreas Kirschning
Journal:  Angew Chem Int Ed Engl       Date:  2020-10-23       Impact factor: 15.336

  10 in total

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