Literature DB >> 18521719

Isotope chirality and asymmetric autocatalysis: a possible entry to biological chirality.

Béla Barabás1, Luciano Caglioti, Károly Micskei, Claudia Zucchi, Gyula Pályi.   

Abstract

Natural-abundance isotopic substitution in isotopically prochiral groups of otherwise achiral molecules can provide stochastically formed enantiomeric excesses which exceed the sensitivity threshold of sensitive asymmetric autocatalytic (Soai-type) reactions. This kind of induction of chirality should be taken into consideration in in vitro model experiments and offer a new kind of entry into primary prebiotic or early biotic enantioselection in the earliest stages of molecular evolution.

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Year:  2008        PMID: 18521719     DOI: 10.1007/s11084-008-9138-1

Source DB:  PubMed          Journal:  Orig Life Evol Biosph        ISSN: 0169-6149            Impact factor:   1.950


  27 in total

1.  Application of asymmetric autocatalysis to the determination of absolute configurations of amino acids with low enantiomeric excesses.

Authors:  K Soai; I Sato
Journal:  Enantiomer       Date:  2001

2.  Enantioselective synthesis without discrete optically active additives.

Authors:  Daniel A Singleton; Loan K Vo
Journal:  J Am Chem Soc       Date:  2002-08-28       Impact factor: 15.419

3.  The asymmetric power of chiral ligands determined by competitive asymmetric autocatalysis.

Authors:  François Lutz; Itaru Sato; Kenso Soai
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005

4.  Small amounts of achiral beta-amino alcohols reverse the enantioselectivity of chiral catalysts in cooperative asymmetric autocatalysis.

Authors:  François Lutz; Takashi Igarashi; Tsuneomi Kawasaki; Kenso Soai
Journal:  J Am Chem Soc       Date:  2005-09-07       Impact factor: 15.419

5.  Screening of combinatorial libraries for substrate preference by mass spectrometry.

Authors:  Stanley M Stevens; Katalin Prokai-Tatrai; Laszlo Prokai
Journal:  Anal Chem       Date:  2005-01-15       Impact factor: 6.986

6.  Empirical description of chiral autocatalysis.

Authors:  Karoly Micskei; György Póta; Luciano Caglioti; Gyula Palyi
Journal:  J Phys Chem A       Date:  2006-05-11       Impact factor: 2.781

7.  The thermodynamic properties of isotopic substances.

Authors:  H C UREY
Journal:  J Chem Soc       Date:  1947-04

Review 8.  Origin of the homochirality of biomolecules.

Authors:  L Keszthelyi
Journal:  Q Rev Biophys       Date:  1995-11       Impact factor: 5.318

Review 9.  Mirror symmetry breaking at the molecular level.

Authors:  V Avetisov; V Goldanskii
Journal:  Proc Natl Acad Sci U S A       Date:  1996-10-15       Impact factor: 11.205

10.  The Macromolecular Route to Chiral Amplification.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-11-02       Impact factor: 15.336

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  7 in total

1.  Homochirality in life: two equal runners, one tripped.

Authors:  Mark M Green; Vipul Jain
Journal:  Orig Life Evol Biosph       Date:  2009-11-13       Impact factor: 1.950

Review 2.  Asymmetric Autocatalysis as an Efficient Link Between the Origin of Homochirality and Highly Enantioenriched Compounds.

Authors:  Kenso Soai; Tsuneomi Kawasaki; Arimasa Matsumoto
Journal:  Orig Life Evol Biosph       Date:  2022-08-12       Impact factor: 1.120

3.  Asymmetric autocatalysis induced by meteoritic amino acids with hydrogen isotope chirality.

Authors:  Tsuneomi Kawasaki; Masako Shimizu; Daisuke Nishiyama; Masateru Ito; Hitomi Ozawa; Kenso Soai
Journal:  Chem Commun (Camb)       Date:  2009-06-24       Impact factor: 6.222

Review 4.  Asymmetric autocatalysis. Chiral symmetry breaking and the origins of homochirality of organic molecules.

Authors:  Kenso Soai
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2019       Impact factor: 3.493

5.  Unidirectional Rotary Motion in Isotopically Chiral Molecular Motors: A Computational Analysis.

Authors:  Jun Wang; Baswanth Oruganti; Bo Durbeej
Journal:  Org Lett       Date:  2020-08-21       Impact factor: 6.005

6.  Quantitative Difference in Solubility of Diastereomeric (2H/1H)-Isotopomers.

Authors:  Tsuneomi Kawasaki; Hiroki Kubo; Satoshi Nishiyama; Taiki Saijo; Rintaro Yokoi; Yuji Tokunaga
Journal:  J Am Chem Soc       Date:  2021-11-05       Impact factor: 15.419

7.  Asymmetric Induction by a Nitrogen 14 N/15 N Isotopomer in Conjunction with Asymmetric Autocatalysis.

Authors:  Arimasa Matsumoto; Hanae Ozaki; Shunya Harada; Kyohei Tada; Tomohiro Ayugase; Hitomi Ozawa; Tsuneomi Kawasaki; Kenso Soai
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-18       Impact factor: 15.336

  7 in total

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