Mass Spectrometry Approach for Differentiation of Positional Isomers of Saccharides: Toward Direct Analysis of Rare Sugars

Amoah, Enoch; Kulyk, Dmytro S.; Callam, Christopher S.; Hadad, Christopher M.; Badu-Tawiah, Abraham K.

doi:10.1021/acs.analchem.2c05375

Mass Spectrometry Approach for Differentiation of Positional Isomers of Saccharides: Toward Direct Analysis of Rare Sugars

Journal Article · Wed Mar 22 04:00:00 UTC 2023 · Analytical Chemistry

DOI:https://doi.org/10.1021/acs.analchem.2c05375· OSTI ID:2422036

Amoah, Enoch ^[1]; ^[2]; ^[2]; Hadad, Christopher M. ^[2]; ^[2]

Department of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States; OSTI
Department of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States

Not provided.

Research Organization:: The Ohio State Univ., Columbus, OH (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0022097

OSTI ID:: 2422036

Journal Information:: Analytical Chemistry, Journal Name: Analytical Chemistry Journal Issue: 13 Vol. 95; ISSN 0003-2700

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (54)

General Strategy for the Synthesis of Rare Sugars via Ru(II)-Catalyzed and Boron-Mediated Selective Epimerization of 1,2-trans-Diols to 1,2-cis-Diols Li, Xiaolei; Wu, Jicheng; Tang, Weiping Journal of the American Chemical Society, Vol. 144, Issue 8 https://doi.org/10.1021/jacs.1c13399	journal	February 2022
Dissecting the Antimicrobial Composition of Honey Nolan, Victoria C.; Harrison, James; Cox, Jonathan A. G. Antibiotics, Vol. 8, Issue 4 https://doi.org/10.3390/antibiotics8040251	journal	December 2019
Joule Heating and Thermal Denaturation of Proteins in Nano-ESI Theta Tips Zhao, Feifei; Matt, Sarah M.; Bu, Jiexun Journal of the American Society for Mass Spectrometry, Vol. 28, Issue 10 https://doi.org/10.1007/s13361-017-1732-x	journal	July 2017
Branching pattern and sequence analysis of underivatized oligosaccharides by combined MS/MS of singly and doubly charged molecular ions in negative-ion electrospray mass spectrometry Chai, Wengang; Lawson, Alexander M.; Piskarev, Vladimir Journal of the American Society for Mass Spectrometry, Vol. 13, Issue 6 https://doi.org/10.1016/S1044-0305(02)00363-X	journal	June 2002
Preclinical assessment ofβ-d-mannuronic acid (M2000) as a non-steroidal anti-inflammatory drug Fattahi, Mohammad Javad; Abdollahi, Mohammad; Agha Mohammadi, Asghar Immunopharmacology and Immunotoxicology, Vol. 37, Issue 6 https://doi.org/10.3109/08923973.2015.1113296	journal	November 2015
Isomaltulose: Recent evidence for health benefits Shyam, Sangeetha; Ramadas, Amutha; Chang, Sui Kiat Journal of Functional Foods, Vol. 48 https://doi.org/10.1016/j.jff.2018.07.002	journal	September 2018
In-Source Microdroplet Derivatization Using Coaxial Contained-Electrospray Mass Spectrometry for Enhanced Sensitivity in Saccharide Analysis Heiss, Derik R.; Badu-Tawiah, Abraham K. Analytical Chemistry, Vol. 93, Issue 50 https://doi.org/10.1021/acs.analchem.1c02897	journal	December 2021
Identification of structurally closely related monosaccharide and disaccharide isomers by PMP labeling in conjunction with IM-MS/MS Yang, Hongmei; Shi, Lei; Zhuang, Xiaoyu Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep28079	journal	June 2016
Enzymatic Process for High-Yield Turanose Production and Its Potential Property as an Adipogenesis Regulator Park, Min-Oh; Lee, Byung-Hoo; Lim, Eunjin Journal of Agricultural and Food Chemistry, Vol. 64, Issue 23 https://doi.org/10.1021/acs.jafc.5b05849	journal	June 2016
Structural analysis of underivatized neutral human milk oligosaccharides in the negative ion mode by nano-electrospray MSn (Part 1: Methodology) Pfenninger, Anja; Karas, Michael; Finke, Berndt Journal of the American Society for Mass Spectrometry, Vol. 13, Issue 11 https://doi.org/10.1016/S1044-0305(02)00645-1	journal	November 2002
Gas-Phase Fragmentation of Cyclic Oligosaccharides in Tandem Mass Spectrometry Chizhov, Alexander O.; Tsvetkov, Yury E.; Nifantiev, Nikolay E. Molecules, Vol. 24, Issue 12 https://doi.org/10.3390/molecules24122226	journal	June 2019
Review: A History of Cyclodextrins Crini, Grégorio Chemical Reviews, Vol. 114, Issue 21 https://doi.org/10.1021/cr500081p	journal	September 2014
Trehalulose Does Not Induce Dental Caries in Rats Infected with Mutans Streptococci Ooshima, T.; Izumitani, A.; Minami, T. Caries Research, Vol. 25, Issue 4 https://doi.org/10.1159/000261376	journal	January 1991
Energy-Resolved Ion Mobility-Mass Spectrometry—A Concept to Improve the Separation of Isomeric Carbohydrates Hoffmann, Waldemar; Hofmann, Johanna; Pagel, Kevin Journal of The American Society for Mass Spectrometry, Vol. 25, Issue 3 https://doi.org/10.1007/s13361-013-0780-0	journal	January 2014
Effect of a preparation containing a fucose‐rich polysaccharide on periorbital wrinkles of human voluntaries Robert, C.; Robert, A. M.; Robert, L. Skin Research and Technology, Vol. 11, Issue 1 https://doi.org/10.1111/j.1600-0846.2005.00100.x	journal	February 2005
Contribution of the Individual Small Intestinal α-Glucosidases to Digestion of Unusual α-Linked Glycemic Disaccharides Lee, Byung-Hoo; Rose, David R.; Lin, Amy Hui-Mei Journal of Agricultural and Food Chemistry, Vol. 64, Issue 33 https://doi.org/10.1021/acs.jafc.6b01816	journal	August 2016
Negative-Ion Electrospray Mass Spectrometry of Neutral Underivatized Oligosaccharides Chai, Wengang; Piskarev, Vladimir; Lawson, Alexander M. Analytical Chemistry, Vol. 73, Issue 3 https://doi.org/10.1021/ac0010126	journal	February 2001
Sn-Beta zeolites with borate salts catalyse the epimerization of carbohydrates via an intramolecular carbon shift Gunther, William R.; Wang, Yuran; Ji, Yuewei Nature Communications, Vol. 3, Issue 1 https://doi.org/10.1038/ncomms2122	journal	January 2012
Rapid, sensitive structure analysis of oligosaccharides Zhao, Yingming; Kent, Stephen B. H.; Chait, Brian T. Proceedings of the National Academy of Sciences, Vol. 94, Issue 5 https://doi.org/10.1073/pnas.94.5.1629	journal	March 1997
Production of Turanose by Cyclomaltodextrin Glucanotransferase from Bacillus stearothermophilus Shibuya, Takashi; Mandai, Takahiko; Kubota, Michio Journal of Applied Glycoscience, Vol. 51, Issue 3 https://doi.org/10.5458/jag.51.223	journal	January 2004
Femtoamp and picoamp modes of electrospray and paper spray ionization Allen, Nicholas R.; Li, Huishan; Cheung, Alexander International Journal of Mass Spectrometry, Vol. 469 https://doi.org/10.1016/j.ijms.2021.116696	journal	November 2021
Enzymatic approaches to rare sugar production Zhang, Wenli; Zhang, Tao; Jiang, Bo Biotechnology Advances, Vol. 35, Issue 2 https://doi.org/10.1016/j.biotechadv.2017.01.004	journal	March 2017
Synthesis of rare sugar isomers through site-selective epimerization Wang, Yong; Carder, Hayden M.; Wendlandt, Alison E. Nature, Vol. 578, Issue 7795 https://doi.org/10.1038/s41586-020-1937-1	journal	January 2020
Rapid Analysis of Monosaccharides in Sub-milligram Plant Samples Using Liquid Chromatography–Mass Spectrometry Assisted by Post-column Derivatization Li, Sha; Cai, Wen-Jing; Wang, Wei Journal of Agricultural and Food Chemistry, Vol. 68, Issue 8 https://doi.org/10.1021/acs.jafc.9b07623	journal	February 2020
Rare Sugars: Recent Advances and Their Potential Role in Sustainable Crop Protection Mijailovic, Nikola; Nesler, Andrea; Perazzolli, Michele Molecules, Vol. 26, Issue 6 https://doi.org/10.3390/molecules26061720	journal	March 2021
Regulation of elastase-type endopeptidase activity, MMP-2 and MMP-9 expression and activation in human dermal fibroblasts by fucose and a fucose-rich polysaccharide Isnard, N.; Péterszegi, G.; Robert, A. M. Biomedicine & Pharmacotherapy, Vol. 56, Issue 5 https://doi.org/10.1016/S0753-3322(02)00196-8	journal	July 2002
Analysis of carbohydrates by chemical ionization mass spectrometry Einolf, W. N.; Magin, D. F.; Chan, W. G. International Journal of Mass Spectrometry and Ion Physics, Vol. 48 https://doi.org/10.1016/0020-7381(83)87096-X	journal	January 1983
LC-MSⁿ Analysis of Isomeric Chondroitin Sulfate Oligosaccharides Using a Chemical Derivatization Strategy Huang, Rongrong; Pomin, Vitor H.; Sharp, Joshua S. Journal of the American Society for Mass Spectrometry, Vol. 22, Issue 9 https://doi.org/10.1007/s13361-011-0174-0	journal	June 2011
Catalytic Isomerization of Biomass-Derived Aldoses: A Review Delidovich, Irina; Palkovits, Regina ChemSusChem, Vol. 9, Issue 6 https://doi.org/10.1002/cssc.201501577	journal	March 2016
Carbohydrate isomer resolutionviamulti-site derivatization cyclic ion mobility-mass spectrometry McKenna, Kristin R.; Li, Li; Baker, Andrew G. The Analyst, Vol. 144, Issue 24 https://doi.org/10.1039/C9AN01584A	journal	January 2019
Structural Characterization of Carbohydrates by Fourier Transform Tandem Mass Spectrometry Zhou, Wen; Hakansson, Kristina Current Proteomics, Vol. 8, Issue 4 https://doi.org/10.2174/157016411798220826	journal	December 2011
The Chemical Composition of Honey Ball, David W. Journal of Chemical Education, Vol. 84, Issue 10 https://doi.org/10.1021/ed084p1643	journal	October 2007
Ion mobility mass spectrometry analysis of isomeric disaccharide precursor, product and cluster ions: Analysis of isomeric disaccharide precursor, product and cluster ions Li, Hongli; Bendiak, Brad; Siems, William F. Rapid Communications in Mass Spectrometry, Vol. 27, Issue 23 https://doi.org/10.1002/rcm.6720	journal	October 2013
Ion mobility-mass spectrometry analysis of isomeric carbohydrate precursor ions Zhu, Maolei; Bendiak, Brad; Clowers, Brian Analytical and Bioanalytical Chemistry, Vol. 394, Issue 7 https://doi.org/10.1007/s00216-009-2865-y	journal	June 2009
Isomaltulose (Palatinose®): a review of biological and toxicological studies Lina, B. A. R.; Jonker, D.; Kozianowski, G. Food and Chemical Toxicology, Vol. 40, Issue 10 https://doi.org/10.1016/S0278-6915(02)00105-9	journal	October 2002
Direct Mass Spectrometry Analysis of Complex Mixtures by Nanoelectrospray with Simultaneous Atmospheric Pressure Chemical Ionization and Electrophoretic Separation Capabilities Kulyk, Dmytro S.; Swiner, Devin J.; Sahraeian, Taghi Analytical Chemistry, Vol. 91, Issue 18 https://doi.org/10.1021/acs.analchem.9b01456	journal	August 2019
Liquid secondary ion mass spectrometry/Fourier transform mass spectrometry of oligosaccharide anions Carroll, James A.; Ngoka, Lambert.; Beggs, Cindy G. Analytical Chemistry, Vol. 65, Issue 11 https://doi.org/10.1021/ac00059a017	journal	June 1993
Recent advances in microbial production of mannitol: utilization of low-cost substrates, strain development and regulation strategies Zhang, Min; Gu, Lei; Cheng, Chao World Journal of Microbiology and Biotechnology, Vol. 34, Issue 3 https://doi.org/10.1007/s11274-018-2425-8	journal	February 2018
Attachment of Chloride Anion to Sugars: Mechanistic Investigation and Discovery of a New Dopant for Efficient Sugar Ionization/Detection in Mass Spectrometers Boutegrabet, Lemia; Kanawati, Basem; Gebefügi, Istvan Chemistry – A European Journal, Vol. 18, Issue 41 https://doi.org/10.1002/chem.201103788	journal	August 2012
Characterization of simple isomeric oligosaccharides and the rapid separation of glycan mixtures by ion mobility mass spectrometry Williams, Jonathan P.; Grabenauer, Megan; Holland, Richard J. International Journal of Mass Spectrometry, Vol. 298, Issue 1-3 https://doi.org/10.1016/j.ijms.2009.08.006	journal	December 2010
Analysis of Sugars and Sugar Polyols in Atmospheric Aerosols by Chloride Attachment in Liquid Chromatography/Negative Ion Electrospray Mass Spectrometry Wan, Eric C. H.; Yu, Jian Zhen Environmental Science & Technology, Vol. 41, Issue 7 https://doi.org/10.1021/es062390g	journal	March 2007
Differentiation of calcium(2+)- and magnesium(2+)-coordinated branched trisaccharide isomers: An electrospray ionization and tandem mass spectrometry study Fura, Aberra.; Leary, Julie A. Analytical Chemistry, Vol. 65, Issue 20 https://doi.org/10.1021/ac00068a017	journal	October 1993
Oligosaccharide analysis using anion attachment in negative mode electrospray mass spectrometry Jiang, Yanjie; Cole, Richard B. Journal of the American Society for Mass Spectrometry, Vol. 16, Issue 1 https://doi.org/10.1016/j.jasms.2004.09.006	journal	January 2005
Efficient Mass Spectrometric Dissection of Glycans via Gold Nanoparticle-Assisted in-Source Cation Adduction Dissociation He, Hui; Wen, Yanrong; Guo, Zhanchen Analytical Chemistry, Vol. 91, Issue 13 https://doi.org/10.1021/acs.analchem.9b01217	journal	June 2019
Safety Evaluation Studies of Leucrose Elias, Peter S.; Benecke, Herta; Schwengers, Dieter Journal of the American College of Toxicology, Vol. 15, Issue 3 https://doi.org/10.3109/10915819609008714	journal	June 1996
Analysis of sugars by liquid chromatography-mass spectrometry in Jerusalem artichoke tubers for bioethanol production optimization Matías, Javier; González, Jerónimo; Royano, Luis Biomass and Bioenergy, Vol. 35, Issue 5 https://doi.org/10.1016/j.biombioe.2011.01.056	journal	May 2011
Honey: Single food stuff comprises many drugs Khan, Shahid Ullah; Anjum, Syed Ishtiaq; Rahman, Khaista Saudi Journal of Biological Sciences, Vol. 25, Issue 2 https://doi.org/10.1016/j.sjbs.2017.08.004	journal	February 2018
On-Demand Ambient Ionization of Picoliter Samples Using Charge Pulses Li, Anyin; Hollerbach, Adam; Luo, Qingjie Angewandte Chemie International Edition, Vol. 54, Issue 23 https://doi.org/10.1002/anie.201501895	journal	April 2015
Tagging saccharides for signal enhancement in mass spectrometric analysis Chang, Yu-Ling; Liao, Sylvain Kuo-Shiang; Chen, Ying-Chu Journal of Mass Spectrometry, Vol. 46, Issue 3 https://doi.org/10.1002/jms.1887	journal	March 2011
Analysis of carbohydrates by atmospheric pressure chloride anion attachment tandem mass spectrometry Vinueza, Nelson R.; Gallardo, Vanessa A.; Klimek, John F. Fuel, Vol. 105 https://doi.org/10.1016/j.fuel.2012.08.012	journal	March 2013
Chloride attachment negative-ion mass spectra of sugars by combined liquid chromatography and atmospheric pressure chemical ionization mass spectrometry Kato, Yoshiaki; Numajiri, Yoko Journal of Chromatography B: Biomedical Sciences and Applications, Vol. 562, Issue 1-2 https://doi.org/10.1016/0378-4347(91)80567-V	journal	January 1991
Identification of sugars and phenolic compounds in honey powders with the use of GC–MS, FTIR spectroscopy, and X-ray diffraction Kozłowicz, Katarzyna; Różyło, Renata; Gładyszewska, Bożena Scientific Reports, Vol. 10, Issue 1 https://doi.org/10.1038/s41598-020-73306-7	journal	October 2020
Studies on skin aging. Preparation and properties of fucose-rich oligo- and polysaccharides. Effect on fibroblast proliferation and survival Péterszegi, G.; Isnard, N.; Robert, A. M. Biomedicine & Pharmacotherapy, Vol. 57, Issue 5-6 https://doi.org/10.1016/S0753-3322(03)00031-3	journal	July 2003
Selective liquid-phase hydrogenation of fructose to d-mannitol over copper-supported metallic nanoparticles Zelin, J.; Meyer, C. I.; Regenhardt, S. A. Chemical Engineering Journal, Vol. 319 https://doi.org/10.1016/j.cej.2017.02.127	journal	July 2017

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