Literature DB >> 15369330

Kinetic evidence for a tetrameric transition state in the asymmetric autocatalytic alkylation of pyrimidyl aldehydes.

Frederic G Buono1, Donna G Blackmond.   

Abstract

Experimental kinetic data coupled with kinetic modeling implicates a tetrameric transition state in the Soai autocatalytic alkylation of pyrimidyl aldehydes. The kinetic model accurately predicts both the reaction rate and the amplification in enantiomeric excess observed in reactions carried out under a wide range of conditions. These studies reveal the Soai reaction to be an example of true autocatalytic efficiency in a template-directed "minimal system" for self-replication.

Entities:  

Year:  2003        PMID： 15369330     DOI： 10.1021/ja034705n

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


  12 in total

1.  From bifunctional to trifunctional (tricomponent nucleophile-transition metal-lewis acid) catalysis: the catalytic, enantioselective α-fluorination of acid chlorides.

Authors:  Jeremy Erb; Daniel H Paull; Travis Dudding; Lee Belding; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

2.  Asymmetric autocatalysis and its implications for the origin of homochirality.

Authors:  Donna G Blackmond
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

3.  The origin of biological homochirality.

Authors:  Donna G Blackmond
Journal:  Philos Trans R Soc Lond B Biol Sci       Date:  2011-10-27       Impact factor: 6.237

Review 4.  The origin of biological homochirality.

Authors:  Donna G Blackmond
Journal:  Cold Spring Harb Perspect Biol       Date:  2010-03-31       Impact factor: 10.005

5.  Stochastic and empirical models of the absolute asymmetric synthesis by the Soai-autocatalysis.

Authors:  Béla Barabás; Claudia Zucchi; Marco Maioli; Károly Micskei; Gyula Pályi
Journal:  J Mol Model       Date:  2015-02-03       Impact factor: 1.810

6.  Spontaneous mirror symmetry breaking in the aldol reaction and its potential relevance in prebiotic chemistry.

Authors:  Michael Mauksch; Shengwei Wei; Matthias Freund; Alexandru Zamfir; Svetlana B Tsogoeva
Journal:  Orig Life Evol Biosph       Date:  2009-11-13       Impact factor: 1.950

Review 7.  The Origin of Biological Homochirality.

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

8.  Mirror-symmetry breaking in the Soai reaction: a kinetic understanding.

Authors:  Jesús Rivera Islas; Dominique Lavabre; Jean-Michel Grevy; Ramón Hernández Lamoneda; Haydée Rojas Cabrera; Jean-Claude Micheau; Thomas Buhse
Journal:  Proc Natl Acad Sci U S A       Date:  2005-09-20       Impact factor: 11.205

9.  Asymmetric autocatalysis: novel structures, novel mechanism?

Authors:  Ilya D Gridnev; John M Brown
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-01       Impact factor: 11.205

10.  Structural Contributions to Autocatalysis and Asymmetric Amplification in the Soai Reaction.

Authors:  Soumitra V Athavale; Adam Simon; K N Houk; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2020-10-14       Impact factor: 15.419
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