A microfluidic strategy for the separation of

enantiomers

Adeline Perro

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Microfluidics for synthetic biology and health applications 2018

• Enantiomeric compounds: same molecular formula and bond sequence so-called “mirror images”

• Two enantiomers exhibit different biological activity in human body

• Chiral synthesis

- Enantioselective catalyst

- Biocatalyst

• Chiral separation

- High performance liquid chromatography (HPLC)

- Gas chromatography (CE)

- Capillary electrophoresis

D. Gheorghe, A. Neacşu, I. Contineanu, S. Tănăsescu and Ş. Perişanu, Journal of Thermal Analysis and Calorimetry, 2017, 130, 1145-1152.M. Jafari, J. Tashkhourian and G. Absalan, Talanta,, 2018, 178, 870-878.J. Xu, Q. Wang, C. Xuan, Q. Xia, X. Lin and Y. Fu, Electroanalysis, 2016, 28, 868-873.

Chirality

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Enantioselective recognition at mesoporous chiral surfaces

C. Wattanakit, Y. B. Come, V. Lapeyre, P. A. Bopp, M. Heim, S. Yadnum, S. Nokbin, C. Warakulwit, J. Limtrakul and A. Kuhn, Nat Commun, 2014, 5, 3325.

Surfactant

Template molecule

C. Wattanakit, T. Yutthalekha, S. Asssavapanumat, V. Lapeyre and A. Kuhn, Nat Commun, 2017, 8, 2087.

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Enantioselective recognition at mesoporous chiral surfaces

Flat Pt L-Dopa imprinted Pt

D-Dopa imprinted Pt After destroyed chiral structure

Different pulse voltammetry of encoded electrodes in various solutions

General concept

Tryptophan (Trp)

L-Trp D-Trp

• Essential amino acid• Protein synthesis in human body• Precursor of neurotransmitter serotonin

• Important Intermediate in the synthesis of peptide antibiotics

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Build a microfluidic device in order to separate the enantiomers

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Hyphenated microfluidic electrochromatography device with a L-Trp-encoded mesoporous platinum film as stationary phase.

Microfluidic device

S. Assavapanumat et al. Angew Chem Int Ed Engl. 2019 doi: 10.1002/anie.201812057

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Chiral surface characterization

Glass

Mesoporous Pt

5 µm

10 µm50 nm

Different pulse voltammetry of encoded electrodes in various solutionsFlat Pt L-Trp imprinted Pt

D-Trp imprinted Pt After destroyed chiral structure

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Chiral surface characterization

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Microfluidic device

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No applied potential

D-Trp L-Trp

Racemic tryptophan discrimination

Racemic tryptophan discrimination with various potential applied

D-Trp L-Trp

200 mV vs Ag/AgCl100 mV vs Ag/AgCl

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L-Tryptophan

D-Tryptophan

S-naproxen

R-naproxen

Racemic discrimination of other chiral molecules

Racemic naproxen discrimination with various potential applied

S-naproxen R-naproxen

200 mV vs Ag/AgCl 300 mV vs Ag/AgCl

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Conclusion

• Tryptophan imprinted mesoporous platinum • In situ fluorescence characterization

Electroseparation of a racemic solution of tryptophan and naproxen

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Microfluidic device:

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Sunpet Assavapanumat

Thittaya Yutthalekha

Neso Sojic

Nanosystèmes Analytiques (NSysA)École nationale supérieure de chimie et de physique (ENSCBP)

Université de Bordeaux, France

Advanced magic porous material (AMPM)Vidyasirimedhi Institute of Science and technology (VISTEC)

Thailand

Chularat Wattanakit

Alexander Kuhn

A microfluidic strategy for the separation of

enantiomers

Adeline Perro

16

Microfluidics for synthetic biology and health applications 2018