The self-disproportionation of enantiomers (SDE): a menace or an opportunity?

Herein we report on the well-documented, yet not widely known, phenomenon of the self-disproportionation of enantiomers (SDE): the spontaneous fractionation of scalemic material into enantioenriched and -depleted fractions when any physicochemical process is applied.

[1]  M. Shimizu,et al.  In vivo formation of a glutathione conjugate derived from thalidomide in humanized uPA-NOG mice. , 2011, Chemical research in toxicology.

[2]  Kenso Soai,et al.  Amplification of a Slight Enantiomeric Imbalance in Molecules Based on Asymmetric Autocatalysis: The First Correlation between High Enantiomeric Enrichment in a Chiral Molecule and Circularly Polarized Light , 1998 .

[3]  Donna J. Nelson,et al.  Self-Disproportionation of Enantiomers via Sublimation; New and Truly Green Dimension in Optical Purification , 2011 .

[4]  V. Soloshonok,et al.  Possible Case of Halogen Bond-Driven Self-Disproportionation of Enantiomers (SDE) via Achiral Chromatography. , 2017, Chemistry.

[5]  M. Netopilík.  Toward ideal separation by size-exclusion chromatography. , 2017, Journal of chromatography. A.

[6]  Jean-Claude Guillemin,et al.  Attempts to explain the self-disproportionation observed in the partial sublimation of enantiomerically enriched carboxylic acids , 2010 .

[7]  V. Schurig.  Elaborate treatment of retention in chemoselective chromatography--the retention increment approach and non-linear effects. , 2009, Journal of chromatography. A.

[8]  P. Cintas,et al.  Asymmetric amplification in amino acid sublimation involving racemic compound to conglomerate conversion. , 2011, Chemical communications.

[9]  Pedro Cintas,et al.  On the physical basis of asymmetry and homochirality. , 2012, Chirality.

[10]  P. Somasundaran.  Foam separation methods , 1972 .

[11]  K. Klika.  Suggested New Terms for Describing Chiral States and the State-Dependent Behavior of Chiral Systems , 2012 .

[12]  P. Schwerdtfeger,et al.  Chiral oxorhenium(V) complexes as candidates for the experimental observation of molecular parity violation: a structural, synthetic and theoretical study. , 2010, Physical chemistry chemical physics : PCCP.

[13]  Vadim A. Soloshonok,et al.  Self-disproportionation of enantiomers of α-trifluoromethyl lactic acid amides via sublimation , 2010 .

[14]  Tsuneomi Kawasaki,et al.  Replication of α-amino acids via Strecker synthesis with amplification and multiplication of chiral intermediate aminonitriles. , 2016, Chemical communications.

[15]  Carolyn Pratt Brock,et al.  On the validity of Wallach's rule: on the density and stability of racemic crystals compared with their chiral counterparts , 1991 .

[16]  Hiroshi Iwamura,et al.  Kinetic rationalization of nonlinear effects in asymmetric catalysis based on phase behavior. , 2006, Angewandte Chemie.

[17]  O. Kitagawa,et al.  Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization. , 2016, Organic letters.

[18]  J. Chickos,et al.  An examination of the thermodynamics of fusion, vaporization, and sublimation of ibuprofen and naproxen by correlation gas chromatography. , 2012, Journal of pharmaceutical sciences.

[19]  O. Trapp,et al.  Nonlinear effects in enantioselective chromatography: prediction of unusual elution profiles of enantiomers in non-racemic mixtures on an achiral stationary phase doped with small amounts of a chiral selector , 2010 .

[20]  John M. Brown,et al.  The Scope of Catalytic Asymmetric Hydroboration/Oxidation with Rhodium Complexes of 1,1′-(2-Diarylphosphino-1-naphthyl)isoquinolines , 1999 .

[21]  V. Davankov.  Separation of enantiomeric compounds using chiral HPLC systems. A brief review of general principles, advances, and development trends , 1989 .

[22]  J. Guillemin,et al.  A simple explanation of the enhancement or depletion of the enantiomeric excess in the partial sublimation of enantiomerically enriched amino acids. , 2010, Chemical communications.

[23]  V. Soloshonok,et al.  Self-disproportionation of enantiomers of (R)-ethyl 3-(3,5-dinitrobenzamido)-4,4,4-trifluorobutanoate on achiral silica gel stationary phase , 2006 .

[24]  X. Cui,et al.  Resolution of omeprazole by inclusion complexation with a chiral host BINOL , 2000 .

[25]  K. Klika,et al.  Remarkable magnitude of the self-disproportionation of enantiomers (SDE) via achiral chromatography: application to the practical-scale enantiopurification of β-amino acid esters , 2016, Amino Acids.

[26]  S. Taudien,et al.  Enantiomeric enrichment of sulfoxides by preparative flash chromatography on an achiral phase , 1994 .

[27]  T. Okada,et al.  Efficient asymmetric synthesis of novel 4-substituted and configurationally stable analogues of thalidomide. , 2006, Organic letters.

[28]  V. Soloshonok,et al.  Diastereoselective α-Alkylation of Metallo Enamines Generated from N-C Axially Chiral Mebroqualone Derivatives. , 2017, Organic letters.

[29]  K. Klika,et al.  A question of policy: should tests for the self-disproportionation of enantiomers (SDE) be mandatory for reports involving scalemates? , 2017 .

[30]  M. Mauksch,et al.  Generation of highly enantioenriched crystalline products in reversible asymmetric reactions with racemic or achiral catalysts. , 2009, Angewandte Chemie.

[31]  N. Harada,et al.  Synthesis, absolute configuration, and enantiomeric enrichment of a cruciferous oxindole phytoalexin, (S)-(-)-spirobrassinin, and its oxazoline analog. , 2001, The Journal of organic chemistry.

[32]  A. Kurganov.  Effect of solute association on the apparent adsorption isotherm. A model of the separation of non-racemic mixtures of enantiomers in achiral chromatographic systems , 1996 .

[33]  V. Soloshonok,et al.  Biomimetic Reductive Amination of Fluoro Aldehydes and Ketones via [1,3]-Proton Shift Reaction.(1) Scope and Limitations. , 1996, The Journal of organic chemistry.

[34]  Ryoji Noyori,et al.  Enantioselective addition of dialkylzincs to aldehydes promoted by chiral amino alcohols. Mechanism and nonlinear effect , 1989 .

[35]  V. Davankov,et al.  A vivid model illustrating chiral recognition induced by achiral structures. , 1990, Chirality.

[36]  M. Morbidelli,et al.  General model for the achiral chromatography of enantiomers forming dimers: application to binaphthol. , 2004, Journal of Chromatography A.

[37]  Karel D. Klika,et al.  Enantiomeric Enrichments via the Self-Disproportionation of Enantiomers (SDE) by Achiral, Gravity-Driven Column Chromatography: a Case Study Using N-(1-Phenylethyl)acetamide for Optimizing the Enantiomerically Pure Yield and Magnitude of the SDE , 2015 .

[38]  M. Mauksch,et al.  Demonstration of spontaneous chiral symmetry breaking in asymmetric Mannich and Aldol reactions. , 2007, Chirality.

[39]  Satoshi Takahashi,et al.  Discrimination of enantiomeric excess of optically active trifluorolactate by distillation: Evidence for a multi-center hydrogen bonding network in the liquid state , 2010 .

[40]  S Zhao,et al.  Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions. , 1986, Journal of the American Chemical Society.

[41]  V. Schurig,et al.  Resolution of non-racemic mixtures in achiral chromatographic systems : a model for the enantioselective effects observed , 1994 .

[42]  Weiguo Song,et al.  Self-disproportionation of enantiomers of prazoles via achiral, gravity-driven silica gel column chromatography , 2013 .

[43]  V. Soloshonok,et al.  Recent Advances in the Asymmetric Synthesis of α-(Trifluoromethyl)-Containing α-Amino Acids , 2012 .

[44]  D. Guillaneux,et al.  NONLINEAR EFFECTS IN ASYMMETRIC CATALYSIS , 1994 .

[45]  Martin A. Suhm,et al.  Chirality-dependent sublimation of α-(trifluoromethyl)-lactic acid: Relative vapor pressures of racemic, eutectic, and enantiomerically pure forms, and vibrational spectroscopy of isolated (S,S) and (S,R) dimers , 2010 .

[46]  V. Svedas,et al.  BIOMIMETIC TRANSAMINATION OF ALPHA -ALKYL BETA -KETO CARBOXYLIC ESTERS. CHEMOENZYMATIC APPROACH TO THE STEREOCHEMICALLY DEFINED ALPHA -ALKYL BETA -FLU OROALKYL BETA -AMINO ACIDS , 1998 .

[47]  P. Cintas,et al.  Enantioenrichment in sublimed amino acid mixtures. , 2012, Chemical communications.

[48]  Manabu Yasumoto,et al.  Phenomenon of optical self-purification of chiral non-racemic compounds. , 2007, Journal of the American Chemical Society.

[49]  K. Uneyama,et al.  Chiral Recognition by Multicenter Single Proton Hydrogen Bonding of Trifluorolactates , 2001 .

[50]  K. Mikami,et al.  Symmetry breaking in asymmetric catalysis: racemic catalysis to autocatalysis. , 2003, Chemical reviews.

[51]  A. Horeau,et al.  Interactions diastereoisomeres d'antipodes en phase liquide , 1974 .

[52]  Christian Girard,et al.  Nonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation. , 1998, Angewandte Chemie.

[53]  Vadim A. Soloshonok,et al.  Self-disproportionation of enantiomers of isopropyl 3,3,3-(trifluoro)lactate via sublimation: Sublimation rates vs. enantiomeric composition , 2010 .

[54]  T. Aida,et al.  Homochiral supramolecular polymerization of an "S"-shaped chiral monomer: translation of optical purity into molecular weight distribution. , 2002, Journal of the American Chemical Society.

[55]  C. Roussel,et al.  Chiral additive induced self-disproportionation of enantiomers under MPLC conditions: preparation of enantiomerically pure samples of 1-(aryl)ethylamines from racemates , 2016 .

[56]  J. Martens,et al.  Purification of Enantiomeric Mixtures in Enantioselective Synthesis: Overlooked Errors and Scientific Basis of Separation in Achiral Environment , 2014 .

[57]  V. Soloshonok,et al.  Self-disproportionation of Enantiomers of Enantiomerically Enriched Compounds. , 2013, Topics in current chemistry.

[58]  Kenso Soai,et al.  Self-replication and amplification of enantiomeric excess of chiral multifunctionalized large molecules by asymmetric autocatalysis. , 2014, Angewandte Chemie.

[59]  P. Schwerdtfeger,et al.  Theoretical investigations into the enantiomeric and racemic forms of α-(trifluoromethyl)lactic acid. , 2011, Physical chemistry chemical physics : PCCP.

[60]  J. Guillemin,et al.  High temperature sublimation of α-amino acids: a realistic prebiotic process leading to large enantiomeric excess. , 2015, Chemical communications.

[61]  R. Noyori,et al.  Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: Chirality Transfer, Multiplication, and Amplification† , 1991 .

[62]  P. Cintas.  Sublime arguments: rethinking the generation of homochirality under prebiotic conditions. , 2008, Angewandte Chemie.

[63]  R. I. Kureshy,et al.  Enantiomer self-disproportionation of chiral compounds on achiral ordered mesoporous silica M41S and regular silica gel as a stationary phase. , 2009, Chirality.

[64]  P. Crooks,et al.  Unexpected pehnomenon in the high-performance liquid chromatographic anlaysis of racemic 14C-labelled nicotine: Separation of enantiomers in a totally achiral system , 1983 .

[65]  Tsuyoshi Nakamura,et al.  Atropisomeric lactam chemistry: catalytic enantioselective synthesis, application to asymmetric enolate chemistry and synthesis of key intermediates for NET inhibitors , 2010 .

[66]  M. Jung,et al.  Computer simulation of three scenarios for the separation of non-racemic mixtures by chromatography on achiral stationary phases , 1992 .

[67]  U. Meierhenrich,et al.  Molecular chirality in meteorites and interstellar ices, and the chirality experiment on board the ESA cometary Rosetta mission. , 2015, Angewandte Chemie.

[68]  M. Morbidelli,et al.  Determination of the Dimerization Equilibrium Constants of Omeprazole and Pirkle's Alcohol through Optical‐Rotation Measurements , 2004 .

[69]  V. Soloshonok,et al.  Rational application of self-disproportionation of enantiomers via sublimation—a novel methodological dimension for enantiomeric purifications , 2010 .

[70]  M. Mauksch,et al.  Evidence of asymmetric autocatalysis in organocatalytic reactions. , 2007, Angewandte Chemie.

[71]  V. Soloshonok,et al.  Self-Disproportionation of Enantiomers (SDE) via achiral gravity-driven column chromatography of N-fluoroacyl-1-phenylethylamines , 2017 .

[72]  Peter Schwerdtfeger,et al.  Progress toward the first observation of parity violation in chiral molecules by high-resolution laser spectroscopy. , 2010, Chirality.

[73]  H. Mauser.  Zur Thermodynamik Optischer Antipoden, I , 1957 .

[74]  K. Burger,et al.  3-Trifluoromethyl- and 3-difluoromethyl-thalidomides , 2004 .

[75]  Michel Petitjean,et al.  Chirality and Symmetry Measures: A Transdisciplinary Review , 2003, Entropy.

[76]  P. Schwerdtfeger,et al.  Reply to the ‘Comment on “Theoretical investigations into the enantiomeric and racemic forms of α-(trifluoromethyl)lactic acid”’ by M. A. Suhm and M. Albrecht, Phys. Chem. Chem. Phys., 2011, 13, DOI: 10.1039/c0cp02455d , 2011 .

[77]  A. Horeau,et al.  Interactions diastereoisomeres d'enantiomeres en phase liquide - II , 1973 .

[78]  Christian Roussel,et al.  Self-disproportionation of enantiomers via achiral chromatography: a warning and an extra dimension in optical purifications. , 2012, Chemical Society reviews.

[79]  Tsuneomi Kawasaki,et al.  Discovery of asymmetric autocatalysis with amplification of chirality and its implication in chiral homogeneity of biomolecules. , 2006, Chirality.

[80]  V. Soloshonok,et al.  Self‐disproportionation of Enantiomers (SDE) of Chiral Nonracemic Amides via Achiral Chromatography , 2016 .

[81]  R. Matusch,et al.  Chromatographic Separation of the Excess Enantiomer under Achiral Conditions , 1989 .

[82]  V. Soloshonok,et al.  Concise asymmetric synthesis of configurationally stable 4-trifluoromethyl thalidomide. , 2009, Future medicinal chemistry.

[83]  Maria Barrio,et al.  Overall stability for the ibuprofen racemate: experimental and topological results leading to the pressure-temperature phase relationships between its racemate and conglomerate. , 2012, The journal of physical chemistry. B.

[84]  B. Sellergren,et al.  Bubble fractionation of enantiomers from solution using molecularly imprinted polymers as collectors. , 1998, Analytical chemistry.

[85]  J. Parr,et al.  Chiral poisoning and asymmetric activation. , 2003, Chemical reviews.

[86]  Etsuko Tokunaga,et al.  Synthesis of fluorinated donepezil by palladium-catalyzed decarboxylative allylation of α-fluoro-β-keto ester with tri-substituted heterocyclic alkene and the self-disproportionation of its enantiomers , 2016 .

[87]  K. Klika,et al.  The self-disproportionation of the enantiomers (SDE) of methyl n-pentyl sulfoxide via achiral, gravity-driven column chromatography: a case study. , 2014, Organic & biomolecular chemistry.

[88]  J. Madarász,et al.  A fast, new method to enhance the enantiomeric purity of non-racemic mixtures: self-disproportionation of enantiomers in the gas antisolvent fractionation of chlorine-substituted mandelic acid derivatives , 2017 .

[89]  J. M. Saa,et al.  Direct, catalytic enantioselective nitroaldol (Henry) reaction of trifluoromethyl ketones: an asymmetric entry to alpha-trifluoromethyl-substituted quaternary carbons. , 2007, Organic letters.

[90]  Vadim A. Soloshonok,et al.  Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography , 2012 .

[91]  E. Juaristi,et al.  Asymmetric Michael addition reaction organocatalyzed by stereoisomeric pyrrolidine sulfinamides under neat conditions. A brief study of self-disproportionation of enantiomers , 2017 .

[92]  O. Wallach,et al.  Zur Kenntniss der Terpene und der ätherischen Oele , 1893 .

[93]  J. Yang,et al.  Highly enantioselective zinc/BINOL-catalyzed alkynylation of α-ketoimine ester: a new entry to optically active quaternary α-CF3 α-amino acids. , 2011, Chemical communications.

[94]  P. G. Wells,et al.  Fluorothalidomide: a characterization of maternal and developmental toxicity in rabbits and mice. , 2011, Toxicological sciences : an official journal of the Society of Toxicology.

[95]  V. Hruby,et al.  Asymmetric synthesis of novel highly sterically constrained (2S,3S)-3-methyl-3-trifluoromethyl- and (2S,3S,4R)-3-trifluoromethyl-4-methylpyroglutamic acids , 1999 .

[96]  Vadim A. Soloshonok,et al.  Self disproportionation of enantiomers of 3,3,3-trifluorolactic acid amides via sublimation , 2010 .

[97]  P. Schwerdtfeger,et al.  Recent experimental and theoretical developments towards the observation of parity violation (PV) effects in molecules by spectroscopy. , 2005, Organic & biomolecular chemistry.

[98]  Etsuko Tokunaga,et al.  Self-disproportionation of enantiomers of heterocyclic compounds having a tertiary trifluoromethyl alcohol center on chromatography with a non-chiral system , 2010 .

[99]  Y. Takéuchi,et al.  (R)- and (S)-3-Fluorothalidomides: Isosteric Analogues of Thalidomide , 1999 .

[100]  Tsuyoshi Nakamura,et al.  Chiral initiator-induces self-disproportionation of enantiomers via achiral chromatography: application to enantiomer separation of racemate , 2013 .

[101]  V. Soloshonok,et al.  Remarkable amplification of the self-disproportionation of enantiomers on achiral-phase chromatography columns. , 2006, Angewandte Chemie.

[102]  R. Noyori,et al.  Quantitative Analysis of the Chiral Amplification in the Amino Alcohol-Promoted Asymmetric Alkylation of Aldehydes with Dialkylzincs , 1998 .

[103]  M. Shimizu,et al.  Human liver microsomal cytochrome P450 3A enzymes involved in thalidomide 5-hydroxylation and formation of a glutathione conjugate. , 2010, Chemical research in toxicology.

[104]  V. Soloshonok,et al.  Self-disproportionation of enantiomers via achiral gravity-driven column chromatography: A case study of N-acyl-α-phenylethylamines. , 2016, Journal of chromatography. A.

[105]  D. Blackmond,et al.  Kinetic aspects of nonlinear effects in asymmetric catalysis. , 2000, Accounts of chemical research.

[106]  Yuya Suzuki,et al.  A comprehensive examination of the self-disproportionation of enantiomers (SDE) of chiral amides via achiral, laboratory-routine, gravity-driven column chromatography , 2015 .

[107]  D. Armstrong,et al.  Foam Flotation Enrichment of Enantiomers , 1994 .

[108]  M. Morbidelli,et al.  Separation of binaphthol enantiomers through achiral chromatography. , 2002, Journal of chromatography. A.

[109]  C. J. McGinn.  DIASTEREOAZEOTROPES AS A MEANS OF RESOLUTION , 1961 .

[110]  L. Corral,et al.  α-Fluoro-substituted thalidomide analogues , 2003 .

[111]  S. Pizzarello,et al.  Alanine enantiomers in the Murchison meteorite , 1998, Nature.

[112]  Karel D. Klika,et al.  Terminology Related to the Phenomenon ‘Self-Disproportionation of Enantiomers’ (SDE) , 2014 .

[113]  J. Jaubert,et al.  Enantiomeric enrichment of non‐racemic mixtures of binaphthol with non‐chiral packings , 1996 .

[114]  S. Hara,et al.  Self-induced chiral recognition in the association of enantiomeric mixtures on silica gel chromatography , 1987 .

[115]  Etsuko Tokunaga,et al.  Synthesis and configurational stability of (S)- and (R)-deuteriothalidomides. , 2010, Chemical & pharmaceutical bulletin.

[116]  Marilyn Miller,et al.  What can we learn from the thalidomide experience: an ophthalmologic perspective , 2011, Current opinion in ophthalmology.

[117]  B. Koppenhoefer,et al.  Is it possible to affect the enantiomeric composition by a simple distillation process? , 1989 .

[118]  V. Soloshonok,et al.  Unconventional preparation of racemic crystals of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate and their unusual crystallographic structure: the ultimate preference for homochiral intermolecular interactions. , 2013, Chemical communications.

[119]  Y. Tu,et al.  Formal synthesis of (-)-cephalotaxine based on a tandem hydroamination/semipinacol rearrangement reaction. , 2012, Chemistry, an Asian journal.

[120]  Diggle Ge.  Thalidomide: 40 years on. , 2001 .

[121]  A. Yudin,et al.  Modified BINOL ligands in asymmetric catalysis. , 2003, Chemical reviews.

[122]  D. Reinhoudt,et al.  Stable Heterotopic Noncovalent Resorcin[4]arene Assemblies , 2000 .

[123]  V. Soloshonok,et al.  Asymmetric aldol reactions of trifluoromethyl ketones with a chiral Ni(II) complex of glycine: Stereocontrolling effect of the trifluoromethyl group , 1996 .

[124]  T. Balaban,et al.  Mimics of the self-assembling chlorosomal bacteriochlorophylls: regio- and stereoselective synthesis and stereoanalysis of acyl(1-hydroxyalkyl)porphyrins. , 2009, Journal of the American Chemical Society.

[125]  Gisela Pracejus.  Optische Aktivierung von N-Phthalyl-α-aminosäure-Derivaten durch tert.-Basen-Katalyse1) , 1959 .

[126]  Toshio Kubota,et al.  Separation of an Enantiomorph and Its Racemate by Distillation: Strong Chiral Recognizing Ability of Trifluorolactates , 1996 .

[127]  I. Zenkevich,et al.  Effects of the dynamic modification of stationary phases by sorbates in gas chromatography: The possibility of separating enantiomers in achiral systems , 2016, Russian Journal of Physical Chemistry A.

[128]  V. Soloshonok,et al.  Practical synthesis of fluorine-containing α- and β-amino acids: recipes from Kiev, Ukraine. , 2009, Future medicinal chemistry.

[129]  H. Kagan,et al.  On diastereomeric perturbations , 2000 .

[130]  O. Kitagawa,et al.  Catalytic enantioselective synthesis of atropisomeric 2-aryl-4-quinolinone derivatives with an N–C chiral axis , 2012 .

[131]  Seiji Tsuzuki,et al.  First principle lattice energy calculations for enantiopure and racemic crystals of α-(trifluoromethyl)lactic acid: Is self-disproportionation of enantiomers controlled by thermodynamic stability of crystals? , 2010 .

[132]  H. Kwart,et al.  Separation of an enantiomorph and its racemate by sublimation , 1967 .

[133]  M. Morbidelli,et al.  Measurement of the Dimerization Equilibrium Constants of Enantiomers , 2002 .

[134]  H. Hara,et al.  Biological evaluation of both enantiomers of fluoro-thalidomide using human myeloma cell line H929 and others , 2017, PloS one.

[135]  M. Mauksch,et al.  Spontaneous emergence of homochirality via coherently coupled antagonistic and reversible reaction cycles. , 2008, Chemphyschem : a European journal of chemical physics and physical chemistry.

[136]  H. Kagan.  Nonlinear Effects in Asymmetric Catalysis: A Personal Account , 2001 .

[137]  Yuya Suzuki,et al.  Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives. , 2016, The Journal of organic chemistry.

[138]  K. Klika,et al.  NMR spectral enantioresolution of spirobrassinin and 1-methoxyspirobrassinin enantiomers using (S)-(―)-ethyl lactate and modeling of spirobrassinin self-association for rationalization of its self-induced diastereomeric anisochromism (SIDA) and enantiomer self-disproportionation on achiral-phase chr , 2010 .

[139]  G. Kminek,et al.  MOD: an organic detector for the future robotic exploration of Mars , 2000 .

[140]  R. Carman,et al.  Partially Racemic Compounds as Brushtail Possum Urinary Metabolites , 1992 .

[141]  M. Verzele,et al.  Preparative liquid chromatography , 1980 .

[142]  R. Cooks,et al.  Serine sublimes with spontaneous chiral amplification. , 2007, Chemical communications.

[143]  Alicja Wzorek,et al.  Optical purifications via self-disproportionation of enantiomers by achiral chromatography: case study of a series of α-CF3-containing secondary alcohols. , 2013, Chirality.

[144]  U. Meierhenrich,et al.  Enantioselective Gas Chromatography in Search of the Origin of Biomolecular Asymmetry in Outer Space , 2016 .

[145]  Ville Nieminen,et al.  NMR and molecular modeling of the dimeric self-association of the enantiomers of 1,1'-bi-2-naphthol and 1-phenyl-2,2,2-trifluoroethanol in the solution state and their relevance to enantiomer self-disproportionation on achiral-phase chromatography (ESDAC). , 2009, Organic & biomolecular chemistry.

[146]  Tsuneomi Kawasaki,et al.  Amplification of chirality as a pathway to biological homochirality , 2010 .

[147]  T. Ishida,et al.  Structure of 5-methoxy-2-([4-methoxy-3,5-dimethyl-2-pyridinyl) methyl]sulfinyl)-1H-benzimidazole (omeprazole). , 1989, Acta crystallographica. Section C, Crystal structure communications.