title: Stochastic and empirical models of the absolute asymmetric synthesis by the Soai-autocatalysis.
abstract: Absolute asymmetric synthesis (AAS) is the preparation of pure (or excess of one) enantiomer of a chiral compound from achiral precursor(s) by a chemical reaction, without enantiopure chiral additive and/or without applied asymmetric physical field. Only one well-characterized example of AAS is known today: the Soai-autocatalysis. In an attempt at clarification of the mechanism of this particular reaction we have undertaken empirical and stochastic analysis of several parallel AAS experiments. Our results show that the initial steps of the reaction might be controlled by simple normal distribution ("coin tossing") formalism. Advanced stages of the reaction, however, appear to be of a more complicated nature. Symmetric beta distribution formalism could not be brought into correspondence with the experimental observations. A bimodal beta distribution algorithm provided suitable agreement with the experimental data. The parameters of this bimodal beta function were determined by a Pólya-urn experiment (simulated by computer). Interestingly, parameters of the resulting bimodal beta function give a golden section ratio. These results show, that in this highly interesting autocatalysis two or even perhaps three catalytic cycles are cooperating. An attempt at constructing a "designed" Soai-type reaction system has also been made.
authors: Institute of Mathematics, University of Technology and Economics of Budapest, 1111, Budapest, Műegyetem rkp. 3/H, Hungary.
authors: Béla
authors: B
authors: Barabás
authors: Claudia
authors: C
authors: Zucchi
authors: Marco
authors: M
authors: Maioli
authors: Károly
authors: K
authors: Micskei
authors: Gyula
authors: G
authors: Pályi
references: J Phys Chem B. 2007 Oct 4;111(39):11506-10
references: 17850066
references: Naturwissenschaften. 1977 Nov;64(11):541-65
references: 593400
references: J Theor Biol. 1997 Aug 21;187(4):583-93
references: 9299301
references: Orig Life Evol Biosph. 2010 Feb;40(1):79-91
references: 19911304
references: J Phys Chem A. 2006 May 11;110(18):5982-4
references: 16671665
references: Chirality. 2007 Nov;19(10 ):816-25
references: 17786910
references: Angew Chem Int Ed Engl. 2007;46(3):393-6
references: 17146824
references: Q Rev Biophys. 1995 Nov;28(4):473-507
references: 8771235
references: Chemistry. 2010 Mar 8;16(10):3147-56
references: 20119988
references: Chirality. 2009 Feb;21(2):299-304
references: 18537164
references: Chirality. 2005 Nov;17(9):511-4
references: 16170794
references: Amino Acids. 2010 May;38(5):1343-50
references: 19763785
references: Chemphyschem. 2009 Aug 24;10(12):2123-31
references: 19504530
references: Proc Natl Acad Sci U S A. 2005 Sep 27;102(39):13743-8
references: 16174731
references: Nature. 1984 Sep 6-11;311(5981):19-23
references: 6472461
references: Chem Rec. 2014 Feb;14(1):70-83
references: 24449510
references: Phys Chem Chem Phys. 2007 Dec 14;9(46):6134-41
references: 18167589
references: Chirality. 2011 Jan;23(1):65-8
references: 20803490
references: Chem Rec. 2004;4(5):267-78
references: 15543607
references: Chem Biodivers. 2010 Jun;7(6):1660-9
references: 20564680
references: J Am Chem Soc. 2003 Jul 30;125(30):8978-9
references: 15369330
references: J Phys Chem A. 2006 Nov 30;110(47):12711-3
references: 17125283
references: Angew Chem Int Ed Engl. 2003 Jan 20;42(3):315-7
references: 12548688
references: J Theor Biol. 1966 Aug;11(3):495-8
references: 5967446
references: Biochim Biophys Acta. 1953 Aug;11(4):459-63
references: 13105666
references: Chemphyschem. 2009 Oct 5;10(14):2508-15
references: 19708050
references: Biosystems. 1975 Jul;7(1):15-21
references: 1156666
references: Angew Chem Int Ed Engl. 2008;47(36):6832-5
references: 18651692
references: Chirality. 2009 Mar;21(3):354-8
references: 18571800
references: Chemphyschem. 2008 Nov 10;9(16):2359-71
references: 18942050
references: J Phys Chem B. 2008 Jul 31;112(30):9196-200
references: 18593153
references: Chirality. 2006 Aug;18(7):479-82
references: 16612805
references: Chem Commun (Camb). 2008 Jul 14;(26):3043-5
references: 18688342
references: J Org Chem. 2010 Apr 2;75(7):2403-6
references: 20196532
references: Orig Life Evol Biosph. 2005 Oct;35(5):461-75
references: 16231209
references: Annu Rev Phys Chem. 2008;59:741-69
references: 18173376
references: Acc Chem Res. 2000 Jun;33(6):382-90
references: 10891056
references: J Phys Chem A. 2005 Dec 8;109(48):11058-63
references: 16331951
references: Acta Crystallogr A. 2009 Sep;65(Pt 5):371-89
references: 19687573
references: Angew Chem Int Ed Engl. 2002 Dec 16;41(24):4618-30
references: 12481315
references: Colloids Surf B Biointerfaces. 2009 Dec 1;74(2):498-503
references: 19647985
references: Orig Life Evol Biosph. 2011 Jun;41(3):249-59
references: 21161387
references: J Org Chem. 2011 Apr 15;76(8):2619-26
references: 21401089
references: J Am Chem Soc. 2001 Oct 17;123(41):10103-4
references: 11592892