Distinguishing enantiomeric amino acids with chiral cyclodextrin adducts and structures for lossless ion manipulations

Nagy, Gabe; Chouinard, Christopher D.; Attah, Isaac K.; Webb, Ian K.; Garimella, Sandilya V.  B.; Ibrahim, Yehia M.; Baker, Erin S.; Smith, Richard D.

doi:10.1002/elps.201800294

Title: Distinguishing enantiomeric amino acids with chiral cyclodextrin adducts and structures for lossless ion manipulations

Journal Article · Mon Sep 17 00:00:00 EDT 2018 · Electrophoresis (Weinheim)

DOI:https://doi.org/10.1002/elps.201800294· OSTI ID:1496792

Nagy, Gabe ^[1]; Chouinard, Christopher D. ^[1]; Attah, Isaac K. ^[1]; Webb, Ian K. ^[1]; Garimella, Sandilya V. B. ^[1]; Ibrahim, Yehia M. ^[1]; Baker, Erin S. ^[1];

^[1]

Biological Sciences DivisionPacific Northwest National Laboratory Richland USA

Enantiomeric molecular evaluations remain an enormous challenge for current analytical techniques. To date, derivatizations strategies and long separation times are generally required in these studies, and the development and implementation of new approaches is greatly desired to increase speed and distinguish currently unresolvable compounds. Herein, we describe a method using chiral cyclodextrin adducts and structures for lossless ion manipulations (SLIM) ion mobility to achieve rapid, high resolution separations of D and L enantiomeric amino acids. In the analyses, chiral cyclodextrin adducts are added to each sample. Two cyclodextrins were found to sandwich each amino acid and form host-guest noncovalent complexes that were distinct for each D and L amino acid pair studied and thus separable with ion mobility (IM) in SLIM devices. The SLIM was also used to accumulate much larger ion populations than previously feasible for evaluation and therefore allow enantiomeric measurements of higher sensitivity and resolution than previously reported by any other IM-based approach.

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Research Organization:: Pacific Northwest National Lab. (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC05-76RL01830

OSTI ID:: 1496792

Report Number(s):: PNNL-SA-136376

Journal Information:: Electrophoresis (Weinheim), Vol. 39, Issue 24; ISSN 0173-0835

Publisher:: Wiley

Country of Publication:: United States

Language:: English

References (43)

Gas-Phase Chiral Separations by Ion Mobility Spectrometry Dwivedi, Prabha; Wu, Ching; Matz, Laura M. Analytical Chemistry, Vol. 78, Issue 24 https://doi.org/10.1021/ac0608772	journal	December 2006
Identifying the D-Pentoses Using Water Adduction to Lithium Cationized Molecule Campbell, Matthew T.; Chen, Dazhe; Glish, Gary L. Journal of The American Society for Mass Spectrometry, Vol. 28, Issue 7 https://doi.org/10.1007/s13361-017-1656-5	journal	April 2017
Exploring Crown Ethers as Shift Reagents for Ion Mobility Spectrometry Hilderbrand, Amy E.; Myung, Sunnie; Clemmer, David E. Analytical Chemistry, Vol. 78, Issue 19 https://doi.org/10.1021/ac060439v	journal	October 2006
Ultra-High Resolution Ion Mobility Separations Utilizing Traveling Waves in a 13 m Serpentine Path Length Structures for Lossless Ion Manipulations Module Deng, Liulin; Ibrahim, Yehia M.; Hamid, Ahmed M. Analytical Chemistry, Vol. 88, Issue 18 https://doi.org/10.1021/acs.analchem.6b01915	journal	August 2016
Chiral and structural analysis of biomolecules using mass spectrometry and ion mobility-mass spectrometry Enders, Jeffrey R.; Mclean, John A. Chirality, Vol. 21, Issue 1E https://doi.org/10.1002/chir.20806	journal	January 2009
Mass spectrometric investigations of α - and β -cyclodextrin complexes with ortho -, meta - and para -coumaric acids by negative mode electrospray ionization Kralj, Bogdan; Šmidovnik, Andrej; Kobe, Jože Rapid Communications in Mass Spectrometry, Vol. 23, Issue 1 https://doi.org/10.1002/rcm.3868	journal	January 2009
A Mass Spectrometry Method for the Determination of Enantiomeric Excess in Mixtures of d , l -Amino Acids Grigorean, Gabriela; Ramirez, Javier; Ahn, Seong He Analytical Chemistry, Vol. 72, Issue 18 https://doi.org/10.1021/ac000061f	journal	September 2000
Characterization of Isomeric Glycans by Reversed Phase Liquid Chromatography-Electronic Excitation Dissociation Tandem Mass Spectrometry Tang, Yang; Wei, Juan; Costello, Catherine E. Journal of The American Society for Mass Spectrometry, Vol. 29, Issue 6 https://doi.org/10.1007/s13361-018-1943-9	journal	April 2018
Synthesis of cationic single-isomer cyclodextrins for the chiral separation of amino acids and anionic pharmaceuticals Tang, Weihua; Ng, Siu-Choon Nature Protocols, Vol. 2, Issue 12 https://doi.org/10.1038/nprot.2007.479	journal	December 2007
Serpentine Ultralong Path with Extended Routing (SUPER) High Resolution Traveling Wave Ion Mobility-MS using Structures for Lossless Ion Manipulations Deng, Liulin; Webb, Ian K.; Garimella, Sandilya V. B. Analytical Chemistry, Vol. 89, Issue 8 https://doi.org/10.1021/acs.analchem.7b00185	journal	April 2017
Distinguishing Biologically Relevant Hexoses by Water Adduction to the Lithium-Cationized Molecule Campbell, Matthew T.; Chen, Dazhe; Wallbillich, Nicholas J. Analytical Chemistry, Vol. 89, Issue 19 https://doi.org/10.1021/acs.analchem.7b02647	journal	September 2017
Compression Ratio Ion Mobility Programming (CRIMP) Accumulation and Compression of Billions of Ions for Ion Mobility-Mass Spectrometry Using Traveling Waves in Structures for Lossless Ion Manipulations (SLIM) Deng, Liulin; Garimella, Sandilya V. B.; Hamid, Ahmed M. Analytical Chemistry, Vol. 89, Issue 12 https://doi.org/10.1021/acs.analchem.7b00189	journal	May 2017
Chiral Measurement of Aspartate and Glutamate in Single Neurons by Large-Volume Sample Stacking Capillary Electrophoresis Patel, Amit V.; Kawai, Takayuki; Wang, Liping Analytical Chemistry, Vol. 89, Issue 22 https://doi.org/10.1021/acs.analchem.7b03435	journal	November 2017
Recent development of cationic cyclodextrins for chiral separation Zhou, Jie; Tang, Jian; Tang, Weihua TrAC Trends in Analytical Chemistry, Vol. 65 https://doi.org/10.1016/j.trac.2014.10.009	journal	February 2015
Cationic cyclodextrin as versatile chiral selector for enantiomeric separation in capillary electrophoresis Dai, Yun; Wang, Shuye; Zhou, Jie Journal of Chromatography A, Vol. 1246 https://doi.org/10.1016/j.chroma.2012.02.065	journal	July 2012
NMR, surface tension and conductivity studies to determine the inclusion mechanism: thermodynamics of host–guest inclusion complexes of natural amino acids in aqueous cyclodextrins Saha, Subhadeep; Ray, Tanusree; Basak, Saptarshi New Journal of Chemistry, Vol. 40, Issue 1 https://doi.org/10.1039/C5NJ02179K	journal	January 2016
The Gas-Phase Chemistry of Cyclodextrin Inclusion Complexes Lebrilla, Carlito B. Accounts of Chemical Research, Vol. 34, Issue 8 https://doi.org/10.1021/ar980125x	journal	August 2001
Enantiomer Separation of Amino Acids by Complexation with Chiral Reference Compounds and High-Field Asymmetric Waveform Ion Mobility Spectrometry: Preliminary Results and Possible Limitations Mie, Axel; Jörntén-Karlsson, Magnus; Axelsson, Bengt-Olof Analytical Chemistry, Vol. 79, Issue 7 https://doi.org/10.1021/ac0618627	journal	April 2007
Fundamentals of ion mobility spectrometry Gabelica, Valérie; Marklund, Erik Current Opinion in Chemical Biology, Vol. 42 https://doi.org/10.1016/j.cbpa.2017.10.022	journal	February 2018
Determining the Binding Sites of β-Cyclodextrin and Peptides by Electron-Capture Dissociation High Resolution Tandem Mass Spectrometry Qi, Yulin; Geib, Timon; Volmer, Dietrich A. Journal of The American Society for Mass Spectrometry, Vol. 26, Issue 7 https://doi.org/10.1007/s13361-015-1118-x	journal	April 2015
Synthesis and Characterization of the Inclusion Complex of Dicationic Ionic Liquid and β-Cyclodextrin Subramaniam, Puvaneswary; Mohamad, Sharifah; Alias, Yatimah International Journal of Molecular Sciences, Vol. 11, Issue 10 https://doi.org/10.3390/ijms11103675	journal	September 2010
Evaluation of the chiral separation ability of single-isomer cationic β-cyclodextrins in capillary electrophoresis: CE and CEC Wang, Yiying; Zhou, Jie; Liu, Yun ELECTROPHORESIS, Vol. 35, Issue 19 https://doi.org/10.1002/elps.201400198	journal	August 2014
Recent innovations in the use of charged cyclodextrins in capillary electrophoresis for chiral separations in pharmaceutical analysis de Boer, Theo; de Zeeuw, Rokus A.; de Jong, Gerhardus J. Electrophoresis, Vol. 21, Issue 15 https://doi.org/10.1002/1522-2683(20000901)21:15<3220::AID-ELPS3220>3.0.CO;2-X	journal	September 2000
A Persubstituted Cationic β-Cyclodextrin for Chiral Separations O'Keeffe, Frank; Shamsi, Shahab A.; Darcy, Raphael Analytical Chemistry, Vol. 69, Issue 23 https://doi.org/10.1021/ac970370e	journal	December 1997
Cyclodextrins in capillary electrophoresis: Recent developments and new trends Escuder-Gilabert, L.; Martín-Biosca, Y.; Medina-Hernández, M. J. Journal of Chromatography A, Vol. 1357 https://doi.org/10.1016/j.chroma.2014.05.074	journal	August 2014
Capillary electrophoresis chiral separations of basic compounds using cationic cyclodextrin Wang, Fang; Khaledi, Morteza G. Electrophoresis, Vol. 19, Issue 12 https://doi.org/10.1002/elps.1150191209	journal	September 1998
Study to explore the mechanism to form inclusion complexes of β-cyclodextrin with vitamin molecules Saha, Subhadeep; Roy, Aditi; Roy, Kanak Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep35764	journal	October 2016
Recent development of cyclodextrin chiral stationary phases and their applications in chromatography Xiao, Yin; Ng, Siu-Choon; Tan, Timothy Thatt Yang Journal of Chromatography A, Vol. 1269 https://doi.org/10.1016/j.chroma.2012.08.049	journal	December 2012
Squeezing of Ion Populations and Peaks in Traveling Wave Ion Mobility Separations and Structures for Lossless Ion Manipulations Using Compression Ratio Ion Mobility Programming Garimella, Sandilya V. B.; Hamid, Ahmed M.; Deng, Liulin Analytical Chemistry, Vol. 88, Issue 23 https://doi.org/10.1021/acs.analchem.6b03660	journal	November 2016
Investigation of an inclusion complex formed by ionic liquid and β-cyclodextrin through hydrophilic and hydrophobic interactions Roy, Mahendra Nath; Roy, Milan Chandra; Roy, Kanak RSC Advances, Vol. 5, Issue 70 https://doi.org/10.1039/C5RA09823H	journal	January 2015
Experimental and Theoretical Investigation of Sodiated Multimers of Steroid Epimers with Ion Mobility-Mass Spectrometry Chouinard, Christopher D.; Cruzeiro, Vinícius Wilian D.; Roitberg, Adrian E. Journal of The American Society for Mass Spectrometry, Vol. 28, Issue 2 https://doi.org/10.1007/s13361-016-1525-7	journal	December 2016
Chiral recognition of amino acid enantiomers using high-definition differential ion mobility mass spectrometry Zhang, J. Diana; Mohibul Kabir, K. M.; Lee, Hyun Eui International Journal of Mass Spectrometry, Vol. 428 https://doi.org/10.1016/j.ijms.2018.02.003	journal	May 2018
Chiral Separations: A Review of Current Topics and Trends Ward, Timothy J.; Ward, Karen D. Analytical Chemistry, Vol. 84, Issue 2 https://doi.org/10.1021/ac202892w	journal	December 2011
Enantioselective separation of dansyl-dl-amino acids and some racemates on “click” functionalized native α-cyclodextrin based sub-2 μm columns Ai, Feng; Wang, Yong; Chen, Hui The Analyst, Vol. 138, Issue 8 https://doi.org/10.1039/c3an36125j	journal	January 2013
Liquid chromatographic separation of enantiomers using a chiral .beta.-cyclodextrin-bonded stationary phase and conventional aqueous-organic mobile phases Hinze, Willie L.; Riehl, Terrence E.; Armstrong, Daniel W. Analytical Chemistry, Vol. 57, Issue 1 https://doi.org/10.1021/ac00279a055	journal	January 1985
Recent developments on polysaccharide-based chiral stationary phases for liquid-phase separation of enantiomers Chankvetadze, Bezhan Journal of Chromatography A, Vol. 1269 https://doi.org/10.1016/j.chroma.2012.10.033	journal	December 2012
Enhancing glycan isomer separations with metal ions and positive and negative polarity ion mobility spectrometry-mass spectrometry analyses Zheng, Xueyun; Zhang, Xing; Schocker, Nathaniel S. Analytical and Bioanalytical Chemistry, Vol. 409, Issue 2 https://doi.org/10.1007/s00216-016-9866-4	journal	September 2016
Investigation of the Complete Suite of the Leucine and Isoleucine Isomers: Toward Prediction of Ion Mobility Separation Capabilities Dodds, James N.; May, Jody C.; McLean, John A. Analytical Chemistry, Vol. 89, Issue 1 https://doi.org/10.1021/acs.analchem.6b04171	journal	December 2016
Multidimensional Analysis of 16 Glucose Isomers by Ion Mobility Spectrometry Gaye, M. M.; Nagy, G.; Clemmer, D. E. Analytical Chemistry, Vol. 88, Issue 4 https://doi.org/10.1021/acs.analchem.5b04280	journal	February 2016
Enantiomeric differentiation of aromatic amino acids using traveling wave ion mobility-mass spectrometry Domalain, Virginie; Hubert-Roux, Marie; Tognetti, Vincent Chem. Sci., Vol. 5, Issue 8 https://doi.org/10.1039/C4SC00443D	journal	January 2014
Application of charged single isomer derivatives of cyclodextrins in capillary electrophoresis for chiral analysis Cucinotta, Vincenzo; Contino, Annalinda; Giuffrida, Alessandro Journal of Chromatography A, Vol. 1217, Issue 7 https://doi.org/10.1016/j.chroma.2009.11.094	journal	February 2010
Processes To Separate Enantiomers Lorenz, Heike; Seidel-Morgenstern, Andreas Angewandte Chemie International Edition, Vol. 53, Issue 5 https://doi.org/10.1002/anie.201302823	journal	January 2014
Ion Mobility Studies of Carbohydrates as Group I Adducts: Isomer Specific Collisional Cross Section Dependence on Metal Ion Radius Huang, Yuting; Dodds, Eric D. Analytical Chemistry, Vol. 85, Issue 20 https://doi.org/10.1021/ac402133f	journal	September 2013

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