Viedma ripening: a reliable crystallisation method to reach single chirality
Open accessAbstract
This tutorial review covers the basic principles behind asymmetric crystallisation processes, with an emphasis on Viedma ripening, and shows that to date many organic molecules can be obtained this way in enantiopure solid form.
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Deracemization of conglomerates through Viedma ripening and asymmetric auto-catalysis with the Soai reaction have recently undergone significant progress.
“The topic has recently undergone significant progress thanks to numerous theoretical models and experimental validations, namely the deracemization of conglomerates through Viedma ripening 55 and the asymmetric auto-catalysis with the Soai reaction.56”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [55]
Viedma ripening was exploited for deracemization of conglomerate-forming achiral or chiral compounds.
“Viedma ripening was exploited for deracemization of conglomerate-forming achiral or chiral compounds (Fig. 15).55,382”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [55]
Under conditions of rare crystal nucleation, rapid growth, and fast racemization in solution, only monomers with chirality matching the primary nuclei crystallize, leading to SMSB.
“Under these circumstances, only monomers with matching chirality to the primary nuclei crystallize leading to SMSB.55,355”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [55]
A racemic mixture can result from a chemical reaction involving prochiral starting materials.
“The racemic mixture can result from chemical reaction involving prochiral starting materials (c).”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [55]
Primary nucleation of an enantiopure 'Eve crystal' of random chirality is slightly amplified by growing under static conditions and strongly amplified by secondary nucleation with magnetic stirring.
“Primary nucleation of an enantiopure 'Eve crystal' of random chirality, slightly amplified by growing under static conditions (top, Havinga-like), or strongly amplified by secondary nucleation thanks to magnetic stirring (bottom, Kondepudi-like) from rapidly racemizing chiral molecules, (S) and (R), or achiral molecules, A.”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [55]
Viedma ripening allows the preparation of enantiopure molecules displaying potent therapeutic activities.
“One example is the Viedma ripening, which allows the preparation of enantiopure molecules displaying potent therapeutic activities.”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [55]
Cites
Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule
Soai, K., Shibata, T., Morioka, H., & Choji, K. (1995) · Nature · doi:10.1038/378767a0 · Cited by 1,085 · see citing works
Emergence of a single solid chiral state from a nearly racemic amino acid derivative
Noorduin, W. L., Izumi, T., Millemaggi, A., Leeman, M., Meekes, H., Van Enckevort, W. J. P., Kellogg, R. M., Kaptein, B., Vlieg, E., & Blackmond, D. G. (2008) · Journal of the American Chemical Society · doi:10.1021/ja7106349 · Cited by 459 · see citing works
Self-citationSoai, K., Sato, I., Shibata, T., Komiya, S., Hayashi, M., Matsueda, Y., Imamura, H., Hayase, T., Morioka, H., Tabira, H., et al. (2003) · Tetrahedron: Asymmetry · doi:10.1016/s0957-4166(02)00791-7 · Cited by 266 · see citing works
Spontaneous formation of optically active substances
Havinga, E. (1954) · Biochimica et Biophysica Acta · doi:10.1016/0006-3002(54)90300-5 · Cited by 221 · see citing works
From Ostwald Ripening to Single Chirality
Noorduin, W. L., Vlieg, E., Kellogg, R. M., & Kaptein, B. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200905215 · Cited by 220 · see citing works
Self-citationKaptein, B., Noorduin, W. L., Meekes, H., van Enckevort, W. J. P., Kellogg, R. M., & Vlieg, E. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802468 · Cited by 134 · see citing works
Self-citationHomochirality beyond grinding: deracemizing chiral crystals by temperature gradient under boiling
Viedma, C., & Cintas, P. (2011) · Chemical Communications · doi:10.1039/c1cc14857e · Cited by 117 · see citing works
Fast attrition-enhanced deracemization of naproxen by a gradual in situ feed
Noorduin, W. L., Kaptein, B., Meekes, H., van Enckevort, W. J. P., Kellogg, R. M., & Vlieg, E. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200901386 · Cited by 101 · see citing works
Self-citationMyrgorodska, I., Meinert, C., Martins, Z., Le Sergeant d'Hendecourt, L., & Meierhenrich, U. J. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201409354 · Cited by 68 · see citing works
El‐Hachemi, Z., Crusats, J., Ribó, J. M., McBride, J. M., & Veintemillas‐Verdaguer, S. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201007209 · Cited by 58 · see citing works
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Buhse, T., Cruz, J.-M., Noble-Terán, M. E., Hochberg, D., Ribó, J. M., Crusats, J., & Micheau, J.-C. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00819 · Cited by 189 · see citing works
Possible chemical and physical scenarios towards biological homochirality
Sallembien, Q., Bouteiller, L., Crassous, J., & Raynal, M. (2022) · Chemical Society Reviews · doi:10.1039/d1cs01179k · Cited by 186 · see citing works
The protometabolic nature of prebiotic chemistry
Nogal, N., Sanz-Sánchez, M., Vela-Gallego, S., Ruiz-Mirazo, K., & de la Escosura, A. (2023) · Chemical Society Reviews · doi:10.1039/d3cs00594a · Cited by 61 · see citing works
Symmetry Breaking in Self-Assembled Nanoassemblies
Sang, Y., & Liu, M. (2019) · Symmetry · doi:10.3390/sym11080950 · Cited by 35 · see citing works
“This transformation process, which is now called Viedma ripening, involves the deracemization of solid-to-solid and solution-to-solid [114,115].”
Background
- Authors
- Sögütoglu, L.-C., Steendam, R. R. E., Meekes, H., Vlieg, E., & Rutjes, F. P. J. T.
- Affiliations
- Radboud University
- Radboud University Nijmegen (NL)
- Corresponding author
- Vlieg, Elias
- Rutjes, Floris P. J. T.
- Venue
- Chemical Society Reviews
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2015
- Volume
- 44
- Issue
- 19
- Pages
- 6723-6732
- ISSN
- 0306-0012 (ISSN-L)
- 1460-4744
- OpenAlex
- W1909037853
- Cited by
- 233
- References
- 10
- Citations by year
- 2026: 12 · 2025: 24 · 2024: 23 · 2023: 29 · 2022: 28 · 2021: 24 · 2020: 25 · 2019: 25 · 2018: 18 · 2017: 9 · 2016: 13 · 2015: 2
- FWCI
- 0.67
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- cc-by
- Locations
- Chemical Society Reviews (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Strathprints: The University of Strathclyde institutional repository (University of Strathclyde) (acceptedVersion)
- Radboud Repository (Radboud University) (submittedVersion)
- Radboud Repository (Radboud University) (submittedVersion, other-oa)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Crystallization and Solubility Studies
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Chemistry › Spectroscopy › Analytical Chemistry and Chromatography
- Keywords
- crystal grinding, asymmetric synthesis, enantiomeric excess
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