ENANTIOMER PURIFICATION THROUGH ACHIRAL CHROMATOGRAPHY: INTEGRATING SIMULATED MOVING BED AND SELF-DISPROPORTIONATION OF ENANTIOMERS

Alicja  Wzorek; Karel Klika; Jianlin  Han; Alexander Sorochinsky; Taizo Ono; Vadim Soloshonok

doi:10.33609/2708-129X.91.3.2025.34-48

Vol. 91 No. 3 (2025), Organic chemistry

Vol. 91 No. 3 (2025)

ENANTIOMER PURIFICATION THROUGH ACHIRAL CHROMATOGRAPHY: INTEGRATING SIMULATED MOVING BED AND SELF-DISPROPORTIONATION OF ENANTIOMERS

Organic chemistry

https://doi.org/10.33609/2708-129X.91.3.2025.34-48

Published April 25, 2025

Alicja Wzorek⁺⁻
Karel Klika⁺⁻
Jianlin Han⁺⁻
Alexander Sorochinsky⁺⁻
Taizo Ono⁺⁻
Vadim Soloshonok⁺⁻

Alicja Wzorek

Institute of Chemistry, Jan Kochanowski University in Kielce, Uniwersytecka 7, 25-406 Kielce, Poland

https://orcid.org/0000-0001-9041-7034

Karel Klika

Molecular Structure Analysis, German Cancer Research Center (DKFZ), ImNeuenheimer Feld 280, 69120 Heidelberg, Germany

https://orcid.org/0000-0001-7009-1487

Jianlin Han

Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

https://orcid.org/0000-0002-3817-0764

Alexander Sorochinsky

Department of Fine Organic Synthesis, V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, The National Academy of Sciences of Ukraine, 1 Murmanska str., Kyiv 02094, Ukraine

https://orcid.org/0000-0002-0132-2664

Taizo Ono

National Institute of Advanced Industrial Science and Technology, 463-8560, Nagoya, Japan

https://orcid.org/0009-0002-3268-2344

Vadim Soloshonok

University of Basque Country

https://orcid.org/0000-0003-0681-4526

№3

Keywords

Chirality, Enantiomers, Purification, Self-Disproportionation of Enantiomers (SDE), Achiral Chromatography, Simulated Moving Bed Chromatography.

How to Cite

Wzorek, A., Klika, K., Han, J., Sorochinsky, A., Ono, T., & Soloshonok, V. (2025). ENANTIOMER PURIFICATION THROUGH ACHIRAL CHROMATOGRAPHY: INTEGRATING SIMULATED MOVING BED AND SELF-DISPROPORTIONATION OF ENANTIOMERS. Ukrainian Chemistry Journal, 91(3), 34-48. https://doi.org/10.33609/2708-129X.91.3.2025.34-48

Abstract

Enantiomer purification is a critical process in the pharmaceutical, agrochemical, and food industries, where chiral compounds often exhibit distinct biological activities. Traditional chiral chromatography is effective but costly due to the use of expensive chiral stationary phases. This review article highlights a recent breakthrough in enantiomer purification under entirely achiral conditions. Specifically, it focuses on the convergence of achiral simulated moving bed chromatography and the phenomenon of self-disproportionation of enantiomers (SDE). Experimental validation using scalemic methyl p-tolyl sulfoxide as a model compound enabled the isolation of the excess enantiomer with high purity (99% ee) and a respectable yield (~50%). This innovative process features exceptional productivity (up to 99 grams per liter of column volume per day), reproducibility, and reliability. This breakthrough presents the first practical example of enantiomer purification based on SDE, offering a scalable and economically viable alternative to conventional chiral separations. Given that SDE is an inherent property of all chiral compounds, this innovative approach is anticipated to become the method of choice for practical enantiomer purification in both research and industrial production.

https://doi.org/10.33609/2708-129X.91.3.2025.34-48

№3

References

Hutt A. J., Tan S. C. Drug Chirality and its Clinical Significance. Drugs. 1996. 52 (Suppl 5): 1–12.

doi.org/10.2165/00003495-199600525-00003.

Lin G. Q., You Q. D., Cheng J. F. Chiral drugs. In Chemistry and Biological Action. Wiley. 2011.

doi:10.1002/9781118075647.

Brooks W. H., Guida W. C., Daniel K. G. The significance of chirality in drug design and development. Curr. Top. Med. Chem. 2011. 11(7): 760–770.

doi: 10.2174/156802611795165098.

Ceramella J., Iacopetta D., Franchini A. et al. A look at the importance of chirality in drug activity: Some significative examples. Appl. Sci. 2022. 12(21): 10909.

doi.org/10.3390/app122110909.

Crossley R. J. Chirality and biological activity of drugs. CRC Press. 1995.

Jianlin Han, Alicja Wzorek, Gagan Dhawan, Wei Zhang, Alexander E. Sorochinsky, Daniel Baecker, Taizo Ono, Karel D. Klika Vadim A. Soloshonok. Chiral fluorine-containing pharmaceuticals. Ukr. Chim. J. 2024. 91(2): 55–90.

Lovering F., Bikker J., Humblet C. Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success. J. Med. Chem. 2009. 52(21): 6752–6756.

doi.org/10.1021/jm901241e.

Calcaterra A., D’Acquarica I. The market of chiral drugs: Chiral switches versus de novo enantiomerically pure compounds. J. Pharmaceut. Biomed. Anal. 2018. 147: 323–340.

doi.org/10.1016/j.jpba.2017.07.008.

Kim J.H, Scialli A.R. Thalidomide: the tragedy of birth defects and the effective treatment of disease. Toxicological sciences. 2011. 122(1): 1–6.

https://doi.org/10.1093/toxsci/kfr088.

Annas G.J., Elias S. Thalidomide and the Titanic: reconstructing the technology tragedies of the twentieth century. American journal of public health. 1999. 89(1): 98–101.

https://doi.org/10.2105/AJPH.89.1.98.

Yamada T., Okada T., Sakaguchi K. et al. Efficient asymmetric synthesis of novel 4-substituted and configurationally stable analogues of thalidomide. Org. Lett. 2006. 8(24): 5625–5628.

doi: 10.1021/ol0623668.

De Camp W.H. Chiral drugs: the FDA perspective on manufacturing and control. Journal of pharmaceutical and biomedical analysis. 1993. 11(11–12): 1167–1172.

https://doi.org/10.1016/0731-7085(93)80100-F.

Rekoske J.E. Chiral separations. American Institute of Chemical Engineers. AIChE Journal. 2001. 47(1): 2. 7327e0c2d7bbd609c 9557102213c3c60.

Sui J., Wang N., Wang J. et al. Strategies for chiral separation: from racemate to enantiomer. Chemical Science. 2023. 14(43): 11955–2003. DOI: 10.1039/D3SC01630G.

Wu D., Pan F., Tan W. et al. Recent progress of enantioseparation under scale production (2014–2019). Journal of separation science. 2020. 43(1): 337–347.

https://doi.org/10.1002/jssc.201900682.

Leek H., Thunberg L., Jonson A.C. et al. Strategy for large-scale isolation of enantiomers in drug discovery. Drug Discovery Today. 2017. 22(1): 133–139.

https://doi.org/10.1016/j.drudis.2016.09.018.

Francotte E.R. Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers. Journal of Chromatography A. 2001. 906(1–2): 379–397.

https://doi.org/10.1016/S0021-9673(00) 00951-1.

Lorenz H., Seidel‐Morgenstern A. Processes to separate enantiomers. Angewandte Chemie International Edition. 2014. 53(5): 1218–1250.

https://doi.org/10.1002/anie.201302823.

Marek W.K., Lee J.W., Seidel-Morgenstern A., Antos D. Separation of nonracemic mixtures of enantiomers by achiral simulated moving bed chromatography. Separation and Purification Technology. 2025. 361: 131497.

doi.org/10.1016/j.seppur.2025.131497.

Han J., Kitagawa O., Wzorek, A. et al. The self-disproportionation of enantiomers (SDE): a menace or an opportunity? Chem. Sci. 2018. 9: 1718–1739,

DOI: 10.1039/C7SC05138G.

Soloshonok V. A., Klika K. D. Terminology Related to the Phenomenon ‘Self-Disproportionation of Enantiomers’ (SDE), Helv. Chem Acta, 2014. 97: 1583–1589.

DOI: 10.1002/hlca.201400122.

Juza M., Mazzotti M., Morbidelli M. Simulated moving-bed chromatography and its application to chirotechnology. Trends in biotechnology. 2000. 18(3): 108–18.

DOI: 10.1016/S0167-7799(99)01419-5.

Seidel‐Morgenstern A., Kessler L.C., Kaspereit M. New developments in simulated moving bed chromatography. Chemical Engineering & Technology: Industrial Chemistry‐Plant Equipment‐Process Engineering-Biotechnology. 2008. 31(6): 826–37.

https://doi.org/10.1002/ceat.200800081.

Soloshonok V.A. Remarkable amplification of the self‐disproportionation of enantiomers on achiral‐phase chromatography columns. Angewandte Chemie International Edition. 2006. 45(5): 766–769.

doi.org/10.1002/anie.200503373.

Soloshonok V.A., Berbasov D.O. Self-disproportionation of enantiomers on achiral phase chromatography. One more example of fluorine’s magic powers. Chim. Oggi Chem. Today. 2006. 24: 44–47.

Soloshonok V.A., Roussel C., Kitagawa O., Sorochinsky A.E. Self-Disproportionation of Enantiomers via Achiral Chromatography: a Warning and Extra Dimension in Optical Purifications, Chem. Soc. Rev. 2012. 41: 4180–4188.

DOI:10.1039/C2CS35006H.

Tanaka K., Osuga H., Suzuki H. et al. J. Chem. Soc., Perkin Trans. 1. 1998. 935–940.

DOI: 10.1039/A707196E.

Matusch R., Coors C. Chromatographic separation of the excess enantiomer under achiral conditions. Angewandte Chemie International Edition in English. 1989. 28(5): 626–627.

doi.org/10.1002/anie.198906261.

Nicoud R.M., Jaubert J.N., Rupprecht I., Kinkel J. Enantiomeric enrichment of non‐racemic mixtures of binaphthol with non‐chiral packings. Chirality. 1996. 8(3): 234–243.

doi.org/10.1002/(SICI)1520-636X(1996) 8:3<234::AID-CHIR2>3.0.CO;2-H.

Baciocchi R., Zenoni G., Mazzotti M., Morbidelli M. Separation of binaphthol enantiomers through achiral chromatography. Journal of Chromatography A. 2002. 944(1–2): 225–240.

doi.org/10.1016/S0021-9673(01)01366-8.

Baciocchi R., Mazzotti M., Morbidelli M. General model for the achiral chromatography of enantiomers forming dimers: application to binaphthol. Journal of Chromatography A. 2004. 1024(1–2): 15–20.

doi.org/10.1016/j.chroma.2003.10.071.

Nakajima M., Kanayama K., Miyoshi I., Hashimoto S.I. Catalytic asymmetric synthesis of binaphthol derivatives by aerobic oxidative coupling of 3-hydroxy-2-naphthoates with chiral diamine-copper complex. Tetrahedron letters. 1995. 36(52): 9519–9520.

doi.org/10.1016/0040-4039(95)02063-2.

Nakajima M., Miyoshi I., Kanayama K. et al. Enantioselective Synthesis of Binaphthol Derivatives by Oxidative Coupling of Naphthol Derivatives Catalyzed by Chiral Diamine-Copper Complexes. J. Org.Chem. 1999. 64(7): 2264–71.

doi.org/10.1021/jo981808t.

Takahashi M., Tanabe H., Nakamura T. et al. Atropisomeric lactam chemistry: catalytic enantioselective synthesis, application to asymmetric enolate chemistry and synthesis of key intermediates for NET inhibitors. Tetrahedron. 2010. 66(1): 288–96.

doi.org/10.1016/j.tet.2009.10.095.

Cundy K.C., Crooks P.A. Unexpected phenomenon in the high-performance liquid chromatographic analysis of racemic 14C-labelled nicotine: Separation of enantiomers in a totally achiral system. Journal of Chromatography A. 1983. 281: 17–33. https://doi.org/10.1016/S0021-9673(01)87863-8.

Charles R., Gil-Av E. Self-amplification of optical activity by chromatography on an achiral adsorbent. Journal of Chromatography A. 1984. 298: 516–20.

doi.org/10.1016/S0021-9673(01)92750-5.

Soloshonok V.A., Berbasov D.O. Self-disproportionation of enantiomers of (R)-ethyl 3-(3, 5-dinitrobenzamido)-4, 4, 4-trifluorobutanoate on achiral silica gel stationary phase. J. Fluor. Chem. 2006. 127(4–5): 597–603.

doi.org/10.1016/j.jfluchem.2005.11.004.

Diter P., Taudien S., Samuel O., Kagan H.B. Enantiomeric enrichment of sulfoxides by preparative flash chromatography on an achiral phase. J. Org. Chem. 1994. 59(2): 370–373.

doi.org/10.1021/jo00081a015.

Wzorek A., Klika K.D., Drabowicz J. et al. The self-disproportionation of the enantiomers (SDE) of methyl n-pentyl sulfoxide via achiral, gravity-driven column chromatography: a case study, Org. Biomol. Chem. 2014. 12: 4738–4746,

DOI: 10.1039/c4ob00831f.

Drabowicz J., Jasiak A., Wzorek A. et al. Self-disproportionation of enantiomers (SDE) of chiral sulfoxides, amides and thioamides via achiral chromatography, Arkivoc 2017. 557–578.

DOI: 10.3998/ark.5550190.0018.200.

Han J., Soloshonok V.A., Klika K. D. et al. Chiral sulfoxides: advances in asymmetric synthesis and problems with the accurate determination of the stereochemical outcome, Chem. Soc. Rev. 2018. 47: 1307–1350.

DOI: 10.1039/c6cs00703a.

Takahata H., Takahashi S., Kouno S.I., Momose T. Symmetry-Assisted Synthesis of C 2-Symmetric trans-α, α ‘-Bis (hydroxymethyl) pyrrolidine and-piperidine Derivatives via Double Sharpless Asymmetric Dihydroxylation of α, ω-Terminal Dienes. J. Org. Chem. 1998. 63(7): 2224–31.

doi.org/10.1021/jo971995f.

Secor R.M. Resolution of Optical Isomers by Crystallization Procedures. Chem. Rev. 1963. 63(3): 297–309.

doi.org/10.1021/cr60223a006.

Fogassy E., Nógrádi M., Kozma D. et al. Optical resolution methods. Org. Biomol. Chem. 2006. 4(16): 3011–30.

doi.org/10.1039/B603058K.

Soloshonok V.A., Ueki H., Yasumoto M. et al. Phenomenon of optical self-purification of chiral non-racemic compounds. J. Am. Chem. Soc. 2007. 129(40): 12112–12113.

doi.org/10.1021/ja065603a.

Pracejus G. Optical Activation of N‐Phthalyl‐α‐Amino Acid Derivatives by Tertiary Base Catalysis. Lieb. Ann. Chem. 1959. 622(1): 10–22.

doi.org/10.1002/jlac.19596220104.

Kwart H., Hoster D.P. Separation of an enantiomorph and its racemate by sublimation. J. Org. Chem. 1967. 32(6): 1867–70.

doi.org/10.1021/jo01281a037.

Garin D.L., Greco D.J., Kelley L. Enhancement of optical activity by fractional sublimation. An alternative to fractional crystallization and a warning. J. Org. Chem. 1977. 42(7): 1249–1251.

doi.org/10.1021/jo00427a033.

Katagiri T., Yoda C., Furuhashi K. et al. Separation of an enantiomorph and its racemate by distillation: strong chiral recognizing ability of trifluorolactates. Chem. Lett. 1996. 25(2): 115–116.

doi.org/10.1246/cl.1996.115.

Katagiri T., Takahashi S., Tsuboi A. et al. Discrimination of enantiomeric excess of optically active trifluorolactate by distillation: Evidence for a multi-center hydrogen bonding network in the liquid state. J. Fluor. Chem. 2010. 131(4): 517–520.

doi.org/10.1016/j.jfluchem.2009.12.007.

Aceña J.L., Sorochinsky A.E., Katagiri T., Soloshonok V.A. 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, Chem. Commun., 2013. 49: 373–375;

DOI: 10.1039/c2cc37491a.

Mastai Y., Völkel A., Cölfen H. Separation of racemate from excess enantiomer of chiral nonracemic compounds via density gradient ultracentrifugation. J. Am. Chem. Soc. 2008. 130(8): 2426–2427.

doi.org/10.1021/ja067905i.

Kozma D., Kassai C., Fogassy E. Enantiomeric enrichment by the use of density differences between racemic compounds and optically active enantiomers. Tetrahedron Lett. 1995. 36(18): 3245–3246.

doi.org/10.1016/0040-4039(95)00454-K

Suzuki Y., Han J., Kitagawa O. et al. A comprehensive examination of the self-disproportionation of enantiomers (SDE) of chiral amides via achiral, laboratory-routine, gravity-driven column chromatography. RSC Adv. 2015. 5(4): 2988–2993.

doi: 10.1039/C4RA13928C.

Wzorek A., Sato A., Drabowicz J. et al. Enantiomeric enrichments via the self-disproportionation of enantiomers (SDE) by achiral, gravity-driven column chromatography: a case study using N-acetyl-1-(phenyl)ethylamine for optimizing the enantiopure yield and magnitude of the SDE, Helv. Chem Acta, 2015. 98: 1147–1159.

DOI: 10.1002/hlca.201500041.

Wzorek A., Sato A., Drabowicz J., Soloshonok V. A. Self-Disproportionation of Enantiomers via achiral gravity-driven column chromatography: a case study of N-Acyl-α-Phenylethylamines, J.Chromatog. A. 2016. 1467: 270–278.

DOI: 10.1016/j.chroma.2016.05.044.

Nakamura T., Tateishi K., Tsukagoshi S. et al. Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography. Tetrahedron. 2012. 68(21): 4013–4017.

doi:10.1016/j.tet.2012.03.054.

Tateishi K., Tsukagoshi S., Nakamura T. et al. Chiral initiator-induces self-disproportionation of enantiomers via achiral chromatography: application to enantiomer separation of racemate, TetrahedronLett. 2013. 54: 5220–5223.

DOI: 10.1016/j.tetlet.2013.07.061.

Goto M., Tateishi K., Ebine K. et al. Chiral additive induced self-disproportionation of enantiomers under MPLC conditions: Preparation of enantiomerically pure samples of 1-(aryl)ethylamines from racemates, Tetrahedron: Asymmetry, 2016. 27: 317–321.

DOI: 10.1016/j.tetasy.2016.03.004.

Wzorek A., Soloshonok V.A., Klika K.D. The Self-Disproportionation of Enantiomers (SDE) of α-Pinene via Evaporation off Silica Gel and Foam Fractionation – Validation of the Plausibility of SDE via Gas Chromatography (GC) for α-Pinene, Separations 2023. 10: 382.

doi.org/10.3390/ separations10070382.

Han J., Wzorek A., Soloshonok V.A., Klika K.D. The self-disproportionation of enantiomers (SDE): the effect of scaling down, potential problems versus prospective applications, possible new occurrences, and unrealized opportunities? Electrophoresis, 2019. 40: 1869–1880.

DOI: 10.1002/elps.201800414.

Kwiatkowska M., Wzorek A., Kolbus A. et al. Flurbiprofen: A Study of the Behavior of the Scalemate by Chromatography, Sublimation, and NMR, Symmetry 2021. 13: 543.

doi.org/ 10.3390/sym13040543.

Soloshonok V.A., Wzorek A., Klika K.D. A question of policy: should tests for the self-disproportionation of enantiomers (SDE) be mandatory for reports involving scalemates? Tetrahedron: Asymmetry. 2017. 28(10): 1430–1434.

doi: 10.1016/j.tetasy.2017.08.020.

Han J., Dembinski R., Soloshonok V. A., Klika K. D. A call for a change in policy regarding the necessity for SDE tests to validate the veracity of the outcome of enantioselective syntheses, the inherent chiral state of natural products, and other cases involving enantioenriched samples. Molecules. 2021. 26(13): 3994.

doi.org/10.3390/molecules26133994.

Han J., Wzorek A., Klika K. D., Soloshonok V. A. Recommended tests for the self-disproportionation of enantiomers (SDE) to ensure accurate reporting of the stereochemical outcome of enantioselective reactions. Molecules. 2021. 26(9): 2757.

doi.org/10.3390/molecules26092757

Han J., Wzorek A., Kwiatkowska M. et al. The self-disproportionation of enantiomers (SDE) of amino acids and their derivatives, Amino Acids, 2019. 51: 865–889.

DOI: 10.1007/s00726-019-02729-y.

Yun Y., Gellman A.J. Adsorption-induced auto-amplification of enantiomeric excess on an achiral surface. Nature Chem. 2015. 7(6): 520–5.

doi.org/10.1038/nchem.2250.

Soai K., Kawasaki T., Matsumoto A. Role of asymmetric autocatalysis in the elucidation of origins of homochirality of organic compounds. Symmetry. 2019. 11(5): 694.

doi.org/10.3390/sym11050694.

Cintas P., Viedma C. On the physical basis of asymmetry and homochirality. Chirality. 2012. 24(11): 894–908.

doi.org/10.1002/chir.22028.

Sorochinsky A.E., Aceña J.L. Soloshonok V.A. Self-Disproportionation of Enantiomers of Chiral, Non-Racemic Fluoroorganic Compounds: Role of Fluorine as Enabling Element, Synthesis 2013. 45: 141–152.

DOI: 10.1055/s-0032-1316812.

Yasumoto M., Ueki H., Soloshonok V.A. Self-Disproportionation of Enantiomers of Trifluoro Lactic Acid Amides via Sublimation, J. Fluor. Chem. 2010. 131: 266–269.

doi.org/10.1016/j.jfluchem.2009.10.002.

Yasumoto M., Ueki H., Ono T. et al. Self-Disproportionation of Enantiomers via Sublimation: Isopropyl 3,3,3-(Trifluoro)-Lactate, J. Fluor. Chem. 2010. 131: 535–539.

doi.org/10.1016/j.jfluchem.2009.11.026.

Yasumoto M., Ueki H., Soloshonok V.A. Self-disproportionation of enantiomers of α-trifluoromethyl lactic acid amides via sublimation. Journal of Fluorine Chemistry. 2010. 131(4): 540–544.

doi.org/10.1016/j.jfluchem.2009.11.010.

Ueki H., Yasumoto M., Soloshonok V.A. Rational application of self-disproportionation of enantiomers via sublimation—a novel methodological dimension for enantiomeric purifications. Tetrahedron: Asymmetry. 2010. 21(11–12): 1396–1400.

doi.org/10.1016/j.tetasy.2010.04.040.

Han J., Nelson D.J., Sorochinsky A.E., Soloshonok V.A. Self-Disproportionation of Enantiomers via Sublimation; New and Truly Green Dimension in Optical Purification, Curr. Org. Synthesis 2011. 8: 310–317.

doi.org/10.2174/157017911794697303.

Sorochinsky A.E., Katagiri T., Ono T. et al. Optical purifications via Self-Disproportionation of Enantiomers by achiral chromatography; Case study of a series of α-CF3-containing secondary alcohols, Chirality 2013. 25: 365–368.

DOI: 10.1002/chir.22180.

Wzorek A., Sato A., Drabowicz J., Soloshonok V.A. Self-disproportionation of enantiomers (SDE) of chiral non-racemic amides via achiral chromatography, Israel J. Chem. 2016. 56: 977–989.

DOI: 10.1002/ijch.201600077.

Wzorek A., Kamizela A., Sato A., Soloshonok, V.A. Self-Disproportionation of Enantiomers (SDE) via achiral gravity-driven column chromatography of N-fluoroacyl-1-phenylethylamines, J. Fluor. Chem. 2017. 196: 37–43.

DOI: 10.1016/j.jfluchem.2016.07.016.

Hosaka T., Imai T., Wzorek A. et al. The self-disproportionation of enantiomers (SDE) of α-amino acid derivatives; facets of steric and electronic properties, Amino Acids, 2019. 51: 283–294.

doi.org/10.1007/s00726-018-2664-x.

Wzorek A., Sato A., Drabowicz J. 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, Amino Acids, 2016. 48: 605–613.

DOI: 10.1007/s00726-015-2152-5

Kwiatkowska M., Marcinkowska M., Wzorek A. et al. The self-disproportionation of enantiomers (SDE) via column chromatography of β-amino-α,α-difluorophosphonic acid derivatives, Amino Acids, 2019. 51: 1377–1385.

DOI: 10.1007/s00726-019-02774-7.

Abás S., Arróniz C., Molins E., Escolano C. Access to the enantiopure pyrrolobenzodiazepine (PBD) dilactam nucleus via self-disproportionation of enantiomers. Tetrahedron, 2018. 74: 867–871.

doi.org/10.1016/j.tet.2018.01.006.

Terada S., Hirai M., Honzawa A. et al. Possible case of halogen bond-driven self-disproportionation of enantiomers (SDE) via achiral chromatography, Chem. Eur. J. 2017. 23: 14631–14638.

DOI: 10.1002/chem.201703308.

Sá Gomes P., Rodrigues A.E. Simulated moving bed chromatography: from concept to proof‐of‐concept. Chem. Eng. Tech. 2012. 35(1): 17–34.

doi.org/10.1002/ceat.201100281.

Mazzotti M., Storti G., Morbidelli M. Optimal operation of simulated moving bed units for nonlinear chromatographic separations. J. Chrom. A. 1997. 769(1): 3–24.

doi.org/10.1016/S0021-9673(97)00048-4.

Rajendran A., Paredes G., Mazzotti M. Simulated moving bed chromatography for the separation of enantiomers. J. Chrom. A. 2009. 1216(4): 709–738.

doi.org/10.1016/j.chroma.2008.10.075.

Hur J.S., Wankat P.C. New design of simulated moving bed (SMB) for ternary separations. Ind. Eng.Chem. Res. 2005. 44(6): 1906–1913.

https://doi.org/10.1021/ie040164e.

Kim K.M., Lee J.W., Kim S. et al. Advanced operating strategies to extend the applications of simulated moving bed chromatography. Chem. Eng. Tech. 2017. 40(12) :2163–2178.

https://doi.org/10.1002/ceat.201700206.

Toumi A., Engell S., Diehl M, et al. J. Efficient optimization of simulated moving bed processes. Chem. Eng. Process.ing: Process Intensification. 2007. 46(11): 1067–1084.

doi.org/10.1016/j.cep.2006.06.026.

Faria R.P., Rodrigues A.E. Instrumental aspects of simulated moving bed chromatography. J. Chrom.A. 2015. 1421: 82–102.

doi.org/10.1016/j.chroma.2015.08.045.

Wu D.J., Xie Y., Ma Z., Wang N.H. Design of simulated moving bed chromatography for amino acid separations. Ind. Eng. Chem. Res. 1998. 37(10): 4023–4035.

doi.org/10.1021/ie9801711.

Guest D.W. Evaluation of simulated moving bed chromatography for pharmaceutical process development. J. Chrom.A. 1997. 760(1): 159–162.

doi.org/10.1016/S0021-9673(96)00903-X.

Azevedo D.C., Rodrigues A.E. Design methodology and operation of a simulated moving bed reactor for the inversion of sucrose and glucose–fructose separation. Chem. Eng. J. 2001. 82(1–3): 95–107.

doi.org/10.1016/S1385-8947(00)00359-4.

Do T.X., Lim Y.I., Lee J., Lee W. Techno-economic analysis of petrochemical complex retrofitted with simulated moving-bed for olefins and aromatics production. Chem. Eng. Res. Design. 2016. 106: 222–241.

doi.org/10.1016/j.cherd.2015.12.020.

Shi Q., Gonçalves J.C., Ferreira A.F., Rodrigues A.E. Simulated moving bed reactor for p-xylene production: Modeling, simulation, and optimization. Chem. Eng. Scien. 2020. 225: 115802.

doi.org/10.1016/j.ces.2020.115802.

Mruc P., Olbrycht M., Korbetskyy M., Antos D. Altering the mobile phase composition to enhance self-disproportionation of enantiomers in achiral chromatography. J. Chrom.A. 2024. 1715: 464603.

doi.org/10.1016/j.chroma.2023.464603.

Olbrycht M., Gumieniak J., Mruc P. et al. Antos, Separation of non-racemic mixtures of enantiomers by achiral chromatography, J. Chrom.A. 2023. 1693: 463877.

doi.org/10.1016/j.chroma.2023.463877.

Ziomek G., Antos D., Tobiska L., Seidel-Morgenstern A. Comparison of possible arrangements of five identical columns in preparative chromatography. J. Chrom.A. 2006. 1116(1–2): 179–188.

doi.org/10.1016/j.chroma.2006.03.065.

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ENANTIOMER PURIFICATION THROUGH ACHIRAL CHROMATOGRAPHY: INTEGRATING SIMULATED MOVING BED AND SELF-DISPROPORTIONATION OF ENANTIOMERS

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