Construction of chiral capillary electrochromatography microsystems based on Aspergillus sp. CM96.
Amino acid
Capillary electrophoresis
Chirality
Graphene oxide
Pectinase
Silica monoliths
Journal
Mikrochimica acta
ISSN: 1436-5073
Titre abrégé: Mikrochim Acta
Pays: Austria
ID NLM: 7808782
Informations de publication
Date de publication:
19 08 2023
19 08 2023
Historique:
received:
18
05
2023
accepted:
20
07
2023
medline:
21
8
2023
pubmed:
19
8
2023
entrez:
19
8
2023
Statut:
epublish
Résumé
Novel chiral capillary electrochromatography (CEC) microsystems were constructed based on Aspergillus sp. CM96. As a newly discovered intrinsic characteristic of the cell, cell chirality occupies an essential position in life evolution. Aspergillus sp. CM96 spore (CM96s) was chosen as a proof of concept to develop chiral capillary columns. Interestingly, various types of amino acid (AA) enantiomers were baseline separated under the optimized conditions. Furthermore, the time-dependent chiral interactions between AAs and CM96s were explored in a wider space. Pectinases generated from Aspergillus sp. CM96 fermentation were immobilized onto graphene oxide-functionalized capillary silica monoliths for separating AA enantiomers. Molecular docking simulations were performed to explore chiral separation mechanisms of pectinase for AA enantiomers. These results indicated that Aspergillus sp. CM96-based CEC microsystems have a significant advantage for chiral separation.
Identifiants
pubmed: 37597027
doi: 10.1007/s00604-023-05926-5
pii: 10.1007/s00604-023-05926-5
doi:
Substances chimiques
Amino Acids
0
Silicon Dioxide
7631-86-9
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
357Informations de copyright
© 2023. The Author(s), under exclusive licence to Springer-Verlag GmbH Austria, part of Springer Nature.
Références
Wang Y, Chen JK, Xiong LX, Wang BJ, Xie SM, Zhang JH, Yuan LM (2022) Preparation of novel chiral stationary phases based on the chiral porous organic cage by thiol-ene click chemistry for enantioseparation in HPLC. Anal Chem 94:4961–4969
doi: 10.1021/acs.analchem.1c03626
pubmed: 35306818
Li D, Sun L, Ding Y, Liu M, Xie L, Liu Y, Shang L, Wu Y, Jiang H, Chi L, Qiu X, Xu W (2021) Water-induced chiral separation on a Au(111) surface. ACS Nano 15:16896–16903
doi: 10.1021/acsnano.1c07842
pubmed: 34652898
Feng F, Zhang S, Yang L, Li G, Xu W, Qu H, Zhang J, Dhinakaran MK, Xu C, Cheng J, Li H (2022) Highly chiral selective resolution in pillar[6]arenes functionalized microchannel membranes. Anal Chem 94:6065–6070
doi: 10.1021/acs.analchem.2c01054
pubmed: 35384661
Fanali C (2019) Enantiomers separation by capillary electrochromatography. TrAC Trends Anal Chem 120:115640
doi: 10.1016/j.trac.2019.115640
Hong T, Liu X, Zhou Q, Liu Y, Guo J, Zhou W, Tan S, Cai Z (2022) What the microscale systems “see” in biological assemblies: cells and viruses? Anal Chem 94:59–74
doi: 10.1021/acs.analchem.1c04244
pubmed: 34812604
Fan J, Ray P, Lu YW, Kaur G, Schwarz JJ, Wan LQ (2018) Cell chirality regulates intercellular junctions and endothelial permeability. Sci Adv 4:eaat2111
doi: 10.1126/sciadv.aat2111
pubmed: 30397640
pmcid: 6200360
Wang S, Furchtgott L, Huang KC, Shaevitz JW (2012) Helical insertion of peptidoglycan produces chiral ordering of the bacterial cell wall. PNAS 109:E595–E604
pubmed: 22343529
pmcid: 3309786
Jing G, Zöttl A, Clément É, Lindner A (2020) Chirality-induced bacterial rheotaxis in bulk shear flows. Sci Adv 6:eabb2012
doi: 10.1126/sciadv.abb2012
pubmed: 32695880
pmcid: 7351478
Chen Y, Jin S, Zhang M, Hu Y, Wu KL, Chung A, Wang S, Tian Z, Wang Y, Wolynes PG, Xiao H (2022) Unleashing the potential of noncanonical amino acid biosynthesis to create cells with precision tyrosine sulfation. Nat Commun 13:5434
doi: 10.1038/s41467-022-33111-4
pubmed: 36114189
pmcid: 9481576
Sauer F, Haas M, Sydow C, Siegle AF, Lauer CA, Trapp O (2021) From amino acid mixtures to peptides in liquid sulphur dioxide on early earth. Nat Commun 12:7182
doi: 10.1038/s41467-021-27527-7
pubmed: 34893619
pmcid: 8664857
Muchowska KB, Moran J (2020) Peptide synthesis at the origin of life. Science 370:767–768
doi: 10.1126/science.abf1698
pubmed: 33184194
Liu Z, Li X, Masai H, Huang X, Tsuda S, Terao J, Yang J, Guo X (2021) A single-molecule electrical approach for amino acid detection and chirality recognition. Sci Adv 7:eabe4365
doi: 10.1126/sciadv.abe4365
pubmed: 33658198
pmcid: 7929498
Wu S, Ye Q, Wu D, Tao Y, Kong Y (2020) Enantioselective recognition of chiral tryptophan with achiral glycine through the strategy of chirality transfer. Anal Chem 92:11927–11934
doi: 10.1021/acs.analchem.0c02335
pubmed: 32786461
Liu H, Shao J, Shi L, Ke W, Zheng F, Zhao Y (2020) Electroactive NPs and D-amino acids oxidase engineered electrochemical chiral sensor for D-alanine detection. Sensor Actuat B-Chem 304:127333
doi: 10.1016/j.snb.2019.127333
Wang L, Gao W, Ng S, Pumera M (2021) Chiral protein-covalent organic framework 3D-printed structures as chiral biosensors. Anal Chem 93:5277–5283
doi: 10.1021/acs.analchem.1c00322
pubmed: 33729747
Ye Q, Guo L, Wu D, Yang B, Tao Y, Deng L, Kong Y (2019) Covalent functionalization of bovine serum albumin with graphene quantum dots for stereospecific molecular recognition. Anal Chem 91:11864–11871
doi: 10.1021/acs.analchem.9b02605
pubmed: 31415149
Zhao Y, Wang Y, Zhang X (2017) Homochiral MOF as circular dichroism sensor for enantioselective recognition on nature and chirality of unmodified amino acids. ACS Appl Mater Interfaces 9:20991–20999
doi: 10.1021/acsami.7b04640
pubmed: 28541029
Suzuki M, Sujino T, Chiba S, Harada Y, Goto M, Takahashi R, Mita M, Hamase K, Kanai T, Ito M, Waldor MK, Yasui M, Sasabe J (2021) Host-microbe cross-talk governs amino acid chirality to regulate survival and differentiation of B cells. Sci Adv 7:eabd6480
doi: 10.1126/sciadv.abd6480
pubmed: 33658193
pmcid: 7929512
Lam H, Oh DC, Cava F, Takacs CN, Clardy J, de Pedro MA, Waldor MK (2009) D-amino acids govern stationary phase cell wall remodeling in bacteria. Science 325:1552–1555
doi: 10.1126/science.1178123
pubmed: 19762646
pmcid: 2759711
Zhao X, Zheng Z, Cai Y, Zhao Y, Zhang Y, Gao Y, Cui Z, Wang X (2020) Accelerated biomethane production from lignocellulosic biomass: pretreated by mixed enzymes secreted by Trichoderma viride and Aspergillus sp. Bioresour Technol 309:123378
doi: 10.1016/j.biortech.2020.123378
pubmed: 32380381
Nguyen MK, Kuzyk A (2019) Reconfigurable chiral plasmonics beyond single chiral centers. ACS Nano 13:13615–13619
doi: 10.1021/acsnano.9b09179
pubmed: 31808671
Ávalos-Ovando O, Besteiro LV, Movsesyan A, Markovich G, Liedl T, Martens K, Wang Z, Correa-Duarte MA, Govorov AO (2021) Chiral photomelting of DNA-nanocrystal assemblies utilizing plasmonic photoheating. Nano Lett 21:7298–7308
doi: 10.1021/acs.nanolett.1c02479
pubmed: 34428053
Pandey S, Mandal S, Danielsen MB, Brown A, Hu C, Christensen NJ, Kulakova AV, Song S, Brown T, Jensen KJ, Wengel J, Lou C, Mao H (2022) Chirality transmission in macromolecular domains. Nat Commun 13:76
doi: 10.1038/s41467-021-27708-4
pubmed: 35013247
pmcid: 8748818
Sevim S, Sorrenti A, Vale JP, El-Hachemi Z, Pané S, Flouris AD, Mayor TS, Puigmartí-Luis J (2022) Chirality transfer from a 3D macro shape to the molecular level by controlling asymmetric secondary flows. Nat Commun 13:1766
doi: 10.1038/s41467-022-29425-y
pubmed: 35365637
pmcid: 8976054
Gerstner E (2010) Nobel Prize 2010: Andre Geim & Konstantin Novoselov. Nature Phys 6:836
doi: 10.1038/nphys1836
Novoselov KS, Geim AK, Morozov SV, Jiang D, Zhang Y, Dubonos SV, Grigorieva IV, Firsov AA (2004) Electric field effect in atomically thin carbon films. Science 306:666–669
doi: 10.1126/science.1102896
pubmed: 15499015
Hong T, Chen X, Xu Y, Cui X, Bai R, Jin C, Li R, Ji Y (2016) Preparation of graphene oxide-modified affinity capillary monoliths based on three types of amino donor for chiral separation and proteolysis. J Chromatogr A 1456:249–256
doi: 10.1016/j.chroma.2016.06.025
pubmed: 27334417
Shi H, Quint DA, Grason GM, Gopinathan A, Huang KC (2020) Chiral twisting in a bacterial cytoskeletal polymer affects filament size and orientation. Nat Commun 11:1408
doi: 10.1038/s41467-020-14752-9
pubmed: 32179732
pmcid: 7075873
Zhao X, Zang SQ, Chen X (2020) Stereospecific interactions between chiral inorganic nanomaterials and biological systems. Chem Soc Rev 49:2481–2503
doi: 10.1039/D0CS00093K
pubmed: 32176233
Tang W, Lu Y, Row KH, Baeck SH, Zhang Y, Sun G (2022) Novel bovine serum album and β-cyclodextrin-based mixed chiral stationary phase for the enantioseparation in capillary electrochromatography. Microchem J 181:107763
doi: 10.1016/j.microc.2022.107763
Sun G, Tang W, Lu Y, Row KH (2022) Enantioseparation by simultaneous biphasic recognition using mobile phase additive and chiral stationary phase in capillary electrochromatography. J Chromatogr A 1666:462856
doi: 10.1016/j.chroma.2022.462856
pubmed: 35123168
Zhang M, Chen J, Xu G, Yu T, Du Y (2023) A chiral metal-organic framework synthesized by the mixture of chiral and non-chiral organic ligands for enantioseparation of drugs by open-tubular capillary electrochromatography. J Chromatogr A 1699:464029
doi: 10.1016/j.chroma.2023.464029
pubmed: 37119710
Sun X, Chen C, Li X, Du Y, Zhao S, Feng Z (2020) Gold nanoparticles coated with a tetramethylammonium lactobionate ionic liquid for enhanced chiral differentiation in open tubular capillary electrochromatography: application to enantioseparation of β-blockers. Microchimica Acta 187:170
doi: 10.1007/s00604-020-4121-2
pubmed: 32060642
Li Y, Xu G, Chen J, Yu T, Miao P, Du Y (2023) One-step synthesis of chiral molecularly imprinted polymer TiO
doi: 10.1007/s00604-023-05854-4
pubmed: 37391671