Organoautocatalysis: Challenges for experiment and theory

Oparin AI: The Origin of Life. Rabochii, Moscow; 1924. Orgel LE: Molecular replication. Nature 1992, 358: 203–209. 10.1038/358203a0 Joyce GF: RNA evolution and the origins of life. Nature 1989, 338: 217–224. 10.1038/338217a0 von Kiedrowski G: A Self-Replicating Hexadeoxynucleotide. Angew Chem Int Ed 1986, 25: 932–935. von Kiedrowski G: Templates, autocatalysis and molecular replication. Pure Appl Chem 1996, 68: 2145–2152. 10.1351/pac199668112145 Sievers D, von Kiedrowski G: Self-replication of complementary nucleotide-based oligomers. Nature 1994, 369: 221–224. 10.1038/369221a0 Patzke V, von Kiedrowski G: Self-replicating systems. ARKIVOC 2007, 5: 293–310. Ludlow RF, Otto S: Systems Chemistry. Chem Soc Rev 2008, 37: 101–108. 10.1039/b611921m Peyrelans JJP, Otto S: Recent highlights in systems chemistry. Curr Opin Chem Biol 2009, 13: 705–713. 10.1016/j.cbpa.2009.08.006 Tjivikua T, Ballester P, Rebek J Jr: Small molecule self-replication. J Am Chem Soc 1990, 112: 1249–1250. 10.1021/ja00159a057 Nowick JS, Feng Q, Tjivikua T, Ballester P, Rebek J Jr: Kinetic studies and modeling of a self-replicating system. J Am Chem Soc 1991, 113: 8831–8839. 10.1021/ja00023a036 Menger FM, Eliseev AV, Khanjin NA: "A self-replicating system": new experimental data and a new mechanistic interpretation. J Am Chem Soc 1994, 116: 3613–3614. 10.1021/ja00087a063 Menger FM, Eliseev AV, Khanjin NA, Sherrod MJ: Evidence for an alternative mechanism to a previously proposed self-replicating system. J Org Chem 1995, 60: 2870–2878. 10.1021/jo00114a043 Reinhoudt DN, Rudkevich DM, de Jong F: Kinetic analysis of the Rebek self-replicating system: is there a controversy? J Am Chem Soc 1996, 118: 6880–6889. 10.1021/ja960324g Lee DH, Granja JR, Martinez JA, Severin K, Ghadiri MR: A self-replicating peptide. Nature 1996, 382: 525–528. 10.1038/382525a0 Quayle J, Slawin A, Philp D: A structurally simple minimal self-replicating system. Tetrahedron Lett 2002, 43: 7229–7233. 10.1016/S0040-4039(02)01613-1 Rubinov B, Wagner N, Rapaport H, Askhenasi G: Self-replicating amphiphilic β-sheet peptides. Angew Chem Int Ed 2009, 48: 6683–6686. 10.1002/anie.200902790 Li T, Nicolaou KC: Chemical self-replication of palindromic duplex DNA. Nature 1994, 369: 218–221. 10.1038/369218a0 Alberts AH, Wynberg H: The role of the product in carbon-carbon bond formation: stoichiometric and catalytic enantioselective autoinduction. J Am Chem Soc 1989, 111: 7265–7266. 10.1021/ja00200a059 Soai K, Niwa S, Hori H: Asymmetric self-catalytic reaction. Self-production of chiral 1-(3-pyridyl)alkanols as chiral self-catalysts in the enantioselective addition of dialkylzinc reagents to pyridine-3-carbaldehyde. J Chem Soc Chem Commun 1990, 982–983. 10.1039/c39900000982 Soai K, Shibata T, Morioka H, Choji K: Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule. Nature 1995, 378: 767–768. 10.1038/378767a0 Shibata T, Morioka H, Hayase T, Choji K, Soai K: Highly enantioselective catalytic asymmetric automultiplication of chiral pyrimidyl alcohol. J Am Chem Soc 1996, 118: 471–472. 10.1021/ja953066g Soai K, Shibata T, Sato I: Enantioselective automultiplication of chiral molecules by asymmetric autocatalysis. Acc Chem Res 2000, 33: 382–390. 10.1021/ar9900820 Mislow K: Absolute asymmetric synthesis: A commentary. Collect Czech Chem Commun 2003, 68: 849–863. 10.1135/cccc20030849 Puchot C, Samuel O, Dunach E, Zhao S, Agami C: Nonlinear Effects in Asymmetric Synthesis. J Am Chem Soc 1986, 108: 2353–2357. 10.1021/ja00269a036 Blackmond DG, McMillan CR, Ramdeehul S, Schrom A, Brown JM: Origins of asymmetric amplification in autocatalytic alkylzinc additions. J Am Chem Soc 2001, 123: 10103–10104. 10.1021/ja0165133 Buono FG, Blackmond DG: Kinetic evidence for a tetrameric transition state in the asymmetric autocatalytic alkylation of pyrimidyl aldehydes. J Am Chem Soc 2003, 125: 8978–8979. 10.1021/ja034705n Schiaffino L, Ercolani G: Amplification of chirality and Enantioselectivity in the asymmetric autocatalytic Soai reaction. ChemPhysChem 2009, 10: 2508–2515. 10.1002/cphc.200900369 Mauksch M, Tsogoeva SB, Martynova IM, Wei S: Evidence of Asymmetric Autocatalysis in Organocatalytic Reactions. Angew Chem Int Ed 2007, 46: 393–396. 10.1002/anie.200603517 Mauksch M, Tsogoeva SB, Martynova IM, Wei S: Demonstration of spontaneous chiral symmetry breaking in asymmetric Mannich and aldol reactions. Chirality 2007, 19: 816–825. 10.1002/chir.20474 Mauksch M, Wei S, Freund M, Zamfir A, Tsogoeva SB: Spontaneous mirror symmetry breaking in the aldol reaction and its potential relevance in prebiotic chemistry. Orig Life Evol Biosp 2010, 40: 79–91. 10.1007/s11084-009-9177-2 Etzenbach-Effers K, Berkessel A: Noncovalent Organocatalysis Based on Hydrogen Bonding: Elucidation of Reaction Paths by Computational Methods. Topics Curr Chem 2009, 291: 1–27. full_text Prins LJ, Reinhoudt DN, Timmerman P: Noncovalent Synthesis Using Hydrogen Bonding. Angew Chem Int Ed 2001, 40: 2382–2426. Publisher Full Text 10.1002/1521-3773(20010702)40:13<2382::AID-ANIE2382>3.0.CO;2-G Hochstim AR: Nonlinear mathematical models for the origin of asymmetry in biological molecules. Orig Life Evol Biosph 1975, 6: 317–366. 10.1007/BF01130337 Crusats J, Hochberg D, Moyano A, Ribó JM: Frank model and spontaneous emergence of chirality in closed systems. ChemPhysChem 2009, 10: 2123–2131. 10.1002/cphc.200900181 Frank CF: On spontaneous asymmetric synthesis. Biochim Biophys Acta 1953, 11: 459–463. 10.1016/0006-3002(53)90082-1 Mauksch M, Tsogoeva SB: Spontaneous emergence of homochirality via coherently coupled antagonistic and reversible reaction cycles. ChemPhysChem 2008, 9: 2359–2372. 10.1002/cphc.200800226 Qian H: Open-System Nonequilibrium Steady State: Statistical Thermodynamics, Fluctuations, and Chemical Oscillations. J Phys Chem B 2006, 110: 15063–15074. 10.1021/jp061858z Plasson R, Bersini H, Commeyras A: Recycling Frank: Spontaneous emergence of homochirality in noncatalytic systems. Proc Natl Acad Sci 2004, 101: 16733–16738. 10.1073/pnas.0405293101 Plasson R: Energetic and entropic analysis of mirror symmetry breaking processes in recycled microreversible chemical systems. J Phys Chem B 2009, 113: 3477–3490. 10.1021/jp803807p Amedjkouh M, Brandberg M: Asymmetric autocatalytic Mannich reaction in the presence of water and its implication in prebiotic chemistry. Chem Commun 2008, 3043–3045. 10.1039/b804142n Wang X, Zhang Y, Tan H, Wang Y, Han P, Wang DZ: Enantioselective Organocatalytic Mannich Reactions with Autocatalysts and Their Mimics. J Org Chem 2010, 75: 2403–2406. 10.1021/jo902500b