A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the...
Transcript of A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the...
![Page 1: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/1.jpg)
A microfluidic strategy for the separation of
enantiomers
Adeline Perro
1
Microfluidics for synthetic biology and health applications 2018
![Page 2: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/2.jpg)
• 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
2
![Page 3: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/3.jpg)
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.
3
![Page 4: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/4.jpg)
4
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
![Page 5: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/5.jpg)
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
5
Build a microfluidic device in order to separate the enantiomers
![Page 6: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/6.jpg)
6
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
![Page 7: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/7.jpg)
7
Chiral surface characterization
Glass
Mesoporous Pt
5 µm
10 µm50 nm
![Page 8: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/8.jpg)
Different pulse voltammetry of encoded electrodes in various solutionsFlat Pt L-Trp imprinted Pt
D-Trp imprinted Pt After destroyed chiral structure
8
Chiral surface characterization
![Page 9: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/9.jpg)
9
Microfluidic device
![Page 10: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/10.jpg)
10
No applied potential
D-Trp L-Trp
Racemic tryptophan discrimination
![Page 11: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/11.jpg)
Racemic tryptophan discrimination with various potential applied
D-Trp L-Trp
200 mV vs Ag/AgCl100 mV vs Ag/AgCl
11
![Page 12: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/12.jpg)
12
L-Tryptophan
D-Tryptophan
S-naproxen
R-naproxen
Racemic discrimination of other chiral molecules
![Page 13: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/13.jpg)
Racemic naproxen discrimination with various potential applied
S-naproxen R-naproxen
200 mV vs Ag/AgCl 300 mV vs Ag/AgCl
7
13
![Page 14: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/14.jpg)
Conclusion
• Tryptophan imprinted mesoporous platinum • In situ fluorescence characterization
Electroseparation of a racemic solution of tryptophan and naproxen
14
Microfluidic device:
![Page 15: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/15.jpg)
15
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
![Page 16: A microfluidic strategy for the separation of enantiomers fileA microfluidic strategy for the separation of enantiomers Adeline Perro 1 Microfluidics for synthetic biology and health](https://reader030.fdocuments.in/reader030/viewer/2022041223/5e0e5168de7a3669521aeb87/html5/thumbnails/16.jpg)
A microfluidic strategy for the separation of
enantiomers
Adeline Perro
16
Microfluidics for synthetic biology and health applications 2018