skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

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

Abstract

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.

Authors:
 [1];  [1];  [1];  [1];  [1];  [1];  [1]; ORCiD logo [1]
  1. Biological Sciences DivisionPacific Northwest National Laboratory Richland USA
Publication Date:
Research Org.:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1496792
Report Number(s):
PNNL-SA-136376
Journal ID: ISSN 0173-0835
DOE Contract Number:  
AC05-76RL01830
Resource Type:
Journal Article
Journal Name:
Electrophoresis (Weinheim)
Additional Journal Information:
Journal Volume: 39; Journal Issue: 24; Journal ID: ISSN 0173-0835
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
chiral separations, cyclodextrins, enantiomers, ion mobility mass spectrometry, structures for lossless ion manipulations

Citation Formats

Nagy, Gabe, Chouinard, Christopher D., Attah, Isaac K., Webb, Ian K., Garimella, Sandilya V. B., Ibrahim, Yehia M., Baker, Erin S., and Smith, Richard D. Distinguishing enantiomeric amino acids with chiral cyclodextrin adducts and structures for lossless ion manipulations. United States: N. p., 2018. Web. doi:10.1002/elps.201800294.
Nagy, Gabe, Chouinard, Christopher D., Attah, Isaac K., Webb, Ian K., Garimella, Sandilya V. B., Ibrahim, Yehia M., Baker, Erin S., & Smith, Richard D. Distinguishing enantiomeric amino acids with chiral cyclodextrin adducts and structures for lossless ion manipulations. United States. doi:10.1002/elps.201800294.
Nagy, Gabe, Chouinard, Christopher D., Attah, Isaac K., Webb, Ian K., Garimella, Sandilya V. B., Ibrahim, Yehia M., Baker, Erin S., and Smith, Richard D. Mon . "Distinguishing enantiomeric amino acids with chiral cyclodextrin adducts and structures for lossless ion manipulations". United States. doi:10.1002/elps.201800294.
@article{osti_1496792,
title = {Distinguishing enantiomeric amino acids with chiral cyclodextrin adducts and structures for lossless ion manipulations},
author = {Nagy, Gabe and Chouinard, Christopher D. and Attah, Isaac K. and Webb, Ian K. and Garimella, Sandilya V. B. and Ibrahim, Yehia M. and Baker, Erin S. and Smith, Richard D.},
abstractNote = {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.},
doi = {10.1002/elps.201800294},
journal = {Electrophoresis (Weinheim)},
issn = {0173-0835},
number = 24,
volume = 39,
place = {United States},
year = {2018},
month = {9}
}

Works referenced in this record:

Gas-Phase Chiral Separations by Ion Mobility Spectrometry
journal, December 2006

  • Dwivedi, Prabha; Wu, Ching; Matz, Laura M.
  • Analytical Chemistry, Vol. 78, Issue 24
  • DOI: 10.1021/ac0608772

Identifying the D-Pentoses Using Water Adduction to Lithium Cationized Molecule
journal, April 2017

  • Campbell, Matthew T.; Chen, Dazhe; Glish, Gary L.
  • Journal of The American Society for Mass Spectrometry, Vol. 28, Issue 7
  • DOI: 10.1007/s13361-017-1656-5

Exploring Crown Ethers as Shift Reagents for Ion Mobility Spectrometry
journal, October 2006

  • Hilderbrand, Amy E.; Myung, Sunnie; Clemmer, David E.
  • Analytical Chemistry, Vol. 78, Issue 19
  • DOI: 10.1021/ac060439v

Chiral and structural analysis of biomolecules using mass spectrometry and ion mobility-mass spectrometry
journal, January 2009

  • Enders, Jeffrey R.; Mclean, John A.
  • Chirality, Vol. 21, Issue 1E
  • DOI: 10.1002/chir.20806

Mass spectrometric investigations of α - and β -cyclodextrin complexes with ortho -, meta - and para -coumaric acids by negative mode electrospray ionization
journal, January 2009

  • Kralj, Bogdan; Šmidovnik, Andrej; Kobe, Jože
  • Rapid Communications in Mass Spectrometry, Vol. 23, Issue 1
  • DOI: 10.1002/rcm.3868

A Mass Spectrometry Method for the Determination of Enantiomeric Excess in Mixtures of d , l -Amino Acids
journal, September 2000

  • Grigorean, Gabriela; Ramirez, Javier; Ahn, Seong He
  • Analytical Chemistry, Vol. 72, Issue 18
  • DOI: 10.1021/ac000061f

Characterization of Isomeric Glycans by Reversed Phase Liquid Chromatography-Electronic Excitation Dissociation Tandem Mass Spectrometry
journal, April 2018

  • Tang, Yang; Wei, Juan; Costello, Catherine E.
  • Journal of The American Society for Mass Spectrometry, Vol. 29, Issue 6
  • DOI: 10.1007/s13361-018-1943-9

Synthesis of cationic single-isomer cyclodextrins for the chiral separation of amino acids and anionic pharmaceuticals
journal, December 2007


Serpentine Ultralong Path with Extended Routing (SUPER) High Resolution Traveling Wave Ion Mobility-MS using Structures for Lossless Ion Manipulations
journal, April 2017


Distinguishing Biologically Relevant Hexoses by Water Adduction to the Lithium-Cationized Molecule
journal, September 2017


Chiral Measurement of Aspartate and Glutamate in Single Neurons by Large-Volume Sample Stacking Capillary Electrophoresis
journal, November 2017


Recent development of cationic cyclodextrins for chiral separation
journal, February 2015


Cationic cyclodextrin as versatile chiral selector for enantiomeric separation in capillary electrophoresis
journal, July 2012


The Gas-Phase Chemistry of Cyclodextrin Inclusion Complexes
journal, August 2001

  • Lebrilla, Carlito B.
  • Accounts of Chemical Research, Vol. 34, Issue 8
  • DOI: 10.1021/ar980125x

Fundamentals of ion mobility spectrometry
journal, February 2018


Determining the Binding Sites of β-Cyclodextrin and Peptides by Electron-Capture Dissociation High Resolution Tandem Mass Spectrometry
journal, April 2015

  • Qi, Yulin; Geib, Timon; Volmer, Dietrich A.
  • Journal of The American Society for Mass Spectrometry, Vol. 26, Issue 7
  • DOI: 10.1007/s13361-015-1118-x

Synthesis and Characterization of the Inclusion Complex of Dicationic Ionic Liquid and β-Cyclodextrin
journal, September 2010

  • Subramaniam, Puvaneswary; Mohamad, Sharifah; Alias, Yatimah
  • International Journal of Molecular Sciences, Vol. 11, Issue 10
  • DOI: 10.3390/ijms11103675

A Persubstituted Cationic β-Cyclodextrin for Chiral Separations
journal, December 1997

  • O'Keeffe, Frank; Shamsi, Shahab A.; Darcy, Raphael
  • Analytical Chemistry, Vol. 69, Issue 23
  • DOI: 10.1021/ac970370e

Cyclodextrins in capillary electrophoresis: Recent developments and new trends
journal, August 2014

  • Escuder-Gilabert, L.; Martín-Biosca, Y.; Medina-Hernández, M. J.
  • Journal of Chromatography A, Vol. 1357
  • DOI: 10.1016/j.chroma.2014.05.074

Capillary electrophoresis chiral separations of basic compounds using cationic cyclodextrin
journal, September 1998


Study to explore the mechanism to form inclusion complexes of β-cyclodextrin with vitamin molecules
journal, October 2016

  • Saha, Subhadeep; Roy, Aditi; Roy, Kanak
  • Scientific Reports, Vol. 6, Issue 1
  • DOI: 10.1038/srep35764

Recent development of cyclodextrin chiral stationary phases and their applications in chromatography
journal, December 2012


Investigation of an inclusion complex formed by ionic liquid and β-cyclodextrin through hydrophilic and hydrophobic interactions
journal, January 2015

  • Roy, Mahendra Nath; Roy, Milan Chandra; Roy, Kanak
  • RSC Advances, Vol. 5, Issue 70
  • DOI: 10.1039/C5RA09823H

Experimental and Theoretical Investigation of Sodiated Multimers of Steroid Epimers with Ion Mobility-Mass Spectrometry
journal, December 2016

  • Chouinard, Christopher D.; Cruzeiro, Vinícius Wilian D.; Roitberg, Adrian E.
  • Journal of The American Society for Mass Spectrometry, Vol. 28, Issue 2
  • DOI: 10.1007/s13361-016-1525-7

Chiral recognition of amino acid enantiomers using high-definition differential ion mobility mass spectrometry
journal, May 2018

  • Zhang, J. Diana; Mohibul Kabir, K. M.; Lee, Hyun Eui
  • International Journal of Mass Spectrometry, Vol. 428
  • DOI: 10.1016/j.ijms.2018.02.003

Chiral Separations: A Review of Current Topics and Trends
journal, December 2011

  • Ward, Timothy J.; Ward, Karen D.
  • Analytical Chemistry, Vol. 84, Issue 2
  • DOI: 10.1021/ac202892w

Liquid chromatographic separation of enantiomers using a chiral .beta.-cyclodextrin-bonded stationary phase and conventional aqueous-organic mobile phases
journal, January 1985

  • Hinze, Willie L.; Riehl, Terrence E.; Armstrong, Daniel W.
  • Analytical Chemistry, Vol. 57, Issue 1
  • DOI: 10.1021/ac00279a055

Enhancing glycan isomer separations with metal ions and positive and negative polarity ion mobility spectrometry-mass spectrometry analyses
journal, September 2016

  • Zheng, Xueyun; Zhang, Xing; Schocker, Nathaniel S.
  • Analytical and Bioanalytical Chemistry, Vol. 409, Issue 2
  • DOI: 10.1007/s00216-016-9866-4

Investigation of the Complete Suite of the Leucine and Isoleucine Isomers: Toward Prediction of Ion Mobility Separation Capabilities
journal, December 2016


Multidimensional Analysis of 16 Glucose Isomers by Ion Mobility Spectrometry
journal, February 2016


Enantiomeric differentiation of aromatic amino acids using traveling wave ion mobility-mass spectrometry
journal, January 2014

  • Domalain, Virginie; Hubert-Roux, Marie; Tognetti, Vincent
  • Chem. Sci., Vol. 5, Issue 8
  • DOI: 10.1039/C4SC00443D

Application of charged single isomer derivatives of cyclodextrins in capillary electrophoresis for chiral analysis
journal, February 2010

  • Cucinotta, Vincenzo; Contino, Annalinda; Giuffrida, Alessandro
  • Journal of Chromatography A, Vol. 1217, Issue 7
  • DOI: 10.1016/j.chroma.2009.11.094

Processes To Separate Enantiomers
journal, January 2014

  • Lorenz, Heike; Seidel-Morgenstern, Andreas
  • Angewandte Chemie International Edition, Vol. 53, Issue 5
  • DOI: 10.1002/anie.201302823

Ion Mobility Studies of Carbohydrates as Group I Adducts: Isomer Specific Collisional Cross Section Dependence on Metal Ion Radius
journal, September 2013

  • Huang, Yuting; Dodds, Eric D.
  • Analytical Chemistry, Vol. 85, Issue 20
  • DOI: 10.1021/ac402133f