Home / Publications / Temperature cycle induced deracemization

Temperature cycle induced deracemization

28
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Intaraboonrod K. et al. Temperature cycle induced deracemization // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 395-405.
GOST all authors (up to 50) Copy
Intaraboonrod K., Lerdwiriyanupap T., Hoquante M., Coquerel G., Flood A. E. Temperature cycle induced deracemization // Mendeleev Communications. 2020. Vol. 30. No. 4. pp. 395-405.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2020.07.002
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.002
TI - Temperature cycle induced deracemization
T2 - Mendeleev Communications
AU - Intaraboonrod, Kritsada
AU - Lerdwiriyanupap, Tharit
AU - Hoquante, Marine
AU - Coquerel, Gerard
AU - Flood, Adrian E
PY - 2020
DA - 2020/06/26
PB - Mendeleev Communications
SP - 395-405
IS - 4
VL - 30
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Intaraboonrod,
author = {Kritsada Intaraboonrod and Tharit Lerdwiriyanupap and Marine Hoquante and Gerard Coquerel and Adrian E Flood},
title = {Temperature cycle induced deracemization},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.002},
number = {4},
pages = {395--405},
doi = {10.1016/j.mencom.2020.07.002}
}
MLA
Cite this
MLA Copy
Intaraboonrod, Kritsada, et al. “Temperature cycle induced deracemization.” Mendeleev Communications, vol. 30, no. 4, Jun. 2020, pp. 395-405. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.07.002.
Views / Downloads
1 / 6

Keywords

chirality
deracemization
enantiopurification
optical resolution
racemization
temperature cycle

Abstract

The problem of separation and purification of the enantiomers of chiral species is a significant issue in the production of modern chemicals of pharmaceutical, agricultural and food industries. Efficient methods enabling a complete conversion of a racemic mixture into the desired enantiomer would be of great benefit to industry. Temperature cycle induced deracemization (TCID), a process allowing an initially racemic crystal phase of a suspension to be converted into an enantiopure state, combines solution phase racemization of the solute molecules and a series of temperature cycles inducing dissolution and crystal growth. The process first described as a more convenient and scalable alternative to Viedma ripening, has now been successfully tested on a wide range of chiral components that are conglomerate forming and racemizable. This review discusses the origins of TCID, potential mechanisms responsible for the deracemization, and also some related processes.

References

2.
Kinetics of chiral symmetry breaking in crystallization
Kondepudi D.K., Bullock K.L., Digits J.A., Hall J.K., Miller J.M.
Journal of the American Chemical Society, 1993
3.
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., Kellogg R.M., Kaptein B., Vlieg E., Blackmond D.G.
Journal of the American Chemical Society, 2008
4.
Absolute Asymmetric Synthesis Involving Chiral Symmetry Breaking in Diels–Alder Reaction
Uemura N., Toyoda S., Shimizu W., Yoshida Y., Mino T., Sakamoto M.
Symmetry, 2020
6.
Intensified deracemization via rapid microwave-assisted temperature cycling
7.
Practical Role of Racemization Rates in Deracemization Kinetics and Process Productivities
Oketani R., Hoquante M., Brandel C., Cardinael P., Coquerel G.
Crystal Growth and Design, 2018
8.
Use of Programmed Damped Temperature Cycles for the Deracemization of a Racemic Suspension of a Conglomerate Forming System
Suwannasang K., Flood A.E., Rougeot C., Coquerel G.
Organic Process Research and Development, 2017
9.
Deracemization of a Racemic Compound via Its Conglomerate-Forming Salt Using Temperature Cycling
Li W.W., Spix L., de Reus S.C., Meekes H., Kramer H.J., Vlieg E., ter Horst J.H.
Crystal Growth and Design, 2016
10.
Temperature Cycling Induced Deracemization of NaClO3 under the Influence of Na2S2O6
Schindler M., Brandel C., Kim W., Coquerel G.
Crystal Growth and Design, 2019
11.
Deracemization of NMPA via Temperature Cycles
Breveglieri F., Maggioni G.M., Mazzotti M.
Crystal Growth and Design, 2018
13.
Complete Deracemization of Proteinogenic Glutamic Acid Using Viedma Ripening on a Metastable Conglomerate
Spix L., Meekes H., Blaauw R.H., van Enckevort W.J., Vlieg E.
Crystal Growth and Design, 2012
14.
Disappearing Conglomerates, Assessment of the Threat
Hoquante M., Sanselme M., Rietveld I.B., Coquerel G.
Crystal Growth and Design, 2019
15.
Photoracemization‐Based Viedma Ripening of a BINOL Derivative
Belletti G., Tortora C., Mellema I.D., Tinnemans P., Meekes H., Rutjes F.P., Tsogoeva S.B., Vlieg E.
Chemistry - A European Journal, 2019
16.
Family of Conglomerate-Forming Systems Composed of Chlocyphos and Alkyl-amine. Assessment of Their Resolution Performances by Using Various Modes of Preferential Crystallization
17.
Detection of order–disorder transition in organic solids by using temperature resolved second harmonic generation (TR-SHG)
Clevers S., Rougeot C., Simon F., Sanselme M., Dupray V., Coquerel G.
Journal of Molecular Structure, 2014
19.
Spotting Conglomerates by Second Harmonic Generation
Galland A., Dupray V., Berton B., Morin-Grognet S., Sanselme M., Atmani H., Coquerel G.
Crystal Growth and Design, 2009
20.
Predicting the Relative Solubilities of Racemic and Enantiopure Crystals by Density-Functional Theory
Otero-de-la-Roza A., Cao B.H., Price I.K., Hein J.E., Johnson E.R.
Angewandte Chemie - International Edition, 2014
21.
Fast Attrition-Enhanced Deracemization of Naproxen by a Gradual In Situ Feed
Noorduin W., Kaptein B., Meekes H., van Enckevort W. ., Kellogg R., Vlieg E.
Angewandte Chemie - International Edition, 2009
22.
10.1016/j.mencom.2020.07.002_bib0110
Wolf
Dynamic Stereochemistry of Chiral Compounds: Principles and Applications, 2007
23.
Attrition-Enhanced Deracemization in the Synthesis of Clopidogrel - A Practical Application of a New Discovery
van der Meijden M.W., Leeman M., Gelens E., Noorduin W.L., Meekes H., van Enckevort W.J., Kaptein B., Vlieg E., Kellogg R.M.
Organic Process Research and Development, 2009
24.
Efficient Havinga–Kondepudi resolution of conglomerate amino acid derivatives by slow cooling and abrasive grinding
Leeman M., Noorduin W.L., Millemaggi A., Vlieg E., Meekes H., van Enckevort W.J., Kaptein B., Kellogg R.M.
CrystEngComm, 2010
25.
Method for the racemization of optically active amino acids
Yamada S., Hongo C., Yoshioka R., Chibata I.
Journal of Organic Chemistry, 1983
26.
Genaev A.M., Salnikov G.E., Shernyukov A.V., Zhu Z., Koltunov K.Y.
Mendeleev Communications, 2018
27.
Solid Phase Deracemization of an Atropisomer
Engwerda A.H., van Schayik P., Jagtenberg H., Meekes H., Rutjes F.P., Vlieg E.
Crystal Growth and Design, 2017
28.
Resolution of an Atropisomeric Naphthamide by Second-Order Asymmetric Transformation: A Highly Productive Technique
Oketani R., Hoquante M., Brandel C., Cardinael P., Coquerel G.
Organic Process Research and Development, 2019
29.
Stereodynamic Quinone–Hydroquinone Molecules That Enantiomerize at sp3-Carbon via Redox-Interconversion
Kim B., Storch G., Banerjee G., Mercado B.Q., Castillo-Lora J., Brudvig G.W., Mayer J.M., Miller S.J.
Journal of the American Chemical Society, 2017
30.
Racemization and Deracemization through Intermolecular Redox Behaviour
Engwerda A.H., Meekes H., Bickelhaupt F.M., Rutjes F.P., Vlieg E.
Chemistry - A European Journal, 2019
31.
Enzymatic Racemization of Leucine and α-Aminobutyrate
OSUMI T., YAMAMOTO T., SODA K.
Agricultural and Biological Chemistry, 1969
33.
The dependence of enzyme activity on temperature: determination and validation of parameters
Peterson M., Daniel R., Danson M., Eisenthal R.
Biochemical Journal, 2007
34.
Studies on Amino Acid Racemases
Johnston M.M., Diven W.F.
Journal of Biological Chemistry, 1969
35.
Enzyme Nomenclature. Recommendations, Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB), https://www.qmul.ac.uk/sbcs/iubmb/enzyme. Accessed 3 January 2020.
36.
Enzyme-assisted physicochemical enantioseparation processes: Part I. Production and characterization of a recombinant amino acid racemase
Würges K., Petrusevska K., Serci S., Wilhelm S., Wandrey C., Seidel-Morgenstern A., Elsner M.P., Lütz S.
Journal of Molecular Catalysis B Enzymatic, 2009
38.
Quantitative Prediction of Rate Constants for Aqueous Racemization To Avoid Pointless Stereoselective Syntheses
Ballard A., Ahmad H.O., Narduolo S., Rosa L., Chand N., Cosgrove D.A., Varkonyi P., Asaad N., Tomasi S., Buurma N.J., Leach A.G.
Angewandte Chemie - International Edition, 2017
41.
Attrition-Enhanced Deracemization of NaClO3: Comparison between Ultrasonic and Abrasive Grinding
Xiouras C., Van Aeken J., Panis J., Ter Horst J.H., Van Gerven T., Stefanidis G.D.
Crystal Growth and Design, 2015
42.
Applications of ultrasound to chiral crystallization, resolution and deracemization
Xiouras C., Fytopoulos A., Jordens J., Boudouvis A.G., Van Gerven T., Stefanidis G.D.
Ultrasonics Sonochemistry, 2018
43.
Particle Breakage Kinetics and Mechanisms in Attrition-Enhanced Deracemization
Xiouras C., Fytopoulos A.A., Ter Horst J.H., Boudouvis A.G., Van Gerven T., Stefanidis G.D.
Crystal Growth and Design, 2018
44.
On the Effect of Secondary Nucleation on Deracemization through Temperature Cycles
Cameli F., ter Horst J.H., Steendam R.R., Xiouras C., Stefanidis G.D.
Chemistry - A European Journal, 2020
45.
Solid state deracemisation of two imine-derivatives of phenylglycine derivatives via high-pressure homogenisation and temperature cycles
Maggioni G.M., Fernández-Ronco M.P., van der Meijden M.W., Kellogg R.M., Mazzotti M.
CrystEngComm, 2018
46.
Mathematical Modeling of Chiral Symmetry Breaking due to Differences in Crystal Growth Kinetics
Suwannasang K., Coquerel G., Rougeot C., Flood A.E.
Chemical Engineering and Technology, 2014
47.
Model of Temperature Cycle-Induced Deracemization via Differences in Crystal Growth Rate Dispersion
Uchin R., Suwannasang K., Flood A.E.
Chemical Engineering and Technology, 2017
49.
Population-Based Mathematical Model of Solid-State Deracemization via Temperature Cycles
51.
Solubility of chiral species as function of the enantiomeric excess
Coquerel G.
Journal of Pharmacy and Pharmacology, 2015
53.
Chiral Symmetry Breaking and Deracemization of Sodium Chlorate in Turbulent Flow
Ahn J., Kim D.H., Coquerel G., Kim W.
Crystal Growth and Design, 2017
54.
Linear Deracemization Kinetics during Viedma Ripening: Autocatalysis Overruled by Chiral Additives
Steendam R.R., Dickhout J., van Enckevort W.J., Meekes H., Raap J., Rutjes F.P., Vlieg E.
Crystal Growth and Design, 2015
55.
Role of Additives during Deracemization Using Temperature Cycling
Belletti G., Meekes H., Rutjes F.P., Vlieg E.
Crystal Growth and Design, 2018
57.
Emergence of single-molecular chirality from achiral reactants
Steendam R.R., Verkade J.M., van Benthem T.J., Meekes H., van Enckevort W.J., Raap J., Rutjes F.P., Vlieg E.
Nature Communications, 2014
58.
Deracemization Controlled by Reaction-Induced Nucleation: Viedma Ripening as a Safety Catch for Total Spontaneous Resolution
Steendam R.R., van Benthem T.J., Huijs E.M., Meekes H., van Enckevort W.J., Raap J., Rutjes F.P., Vlieg E.
Crystal Growth and Design, 2015
59.
10.1016/j.mencom.2020.07.002_bib0295
Guillot
Angew. Chem., Int. Ed., 2020