Understanding the fragmentation of glucose in mass spectrometry.
CID
IRMPD
carbohydrate
fragmentation
glucose
stable isotope label
tandem mass spectrometry
Journal
Journal of mass spectrometry : JMS
ISSN: 1096-9888
Titre abrégé: J Mass Spectrom
Pays: England
ID NLM: 9504818
Informations de publication
Date de publication:
Oct 2023
Oct 2023
Historique:
revised:
27
06
2023
received:
30
01
2023
accepted:
21
07
2023
medline:
30
10
2023
pubmed:
24
8
2023
entrez:
24
8
2023
Statut:
ppublish
Résumé
The fragmentation mechanism of D-glucose was investigated in detail by two different fragmentation techniques, namely, collision-induced dissociation (CID) and infrared multiphoton dissociation (IRMPD) using all six
Substances chimiques
Glucose
IY9XDZ35W2
Ions
0
Carbohydrates
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e4972Informations de copyright
© 2023 John Wiley & Sons Ltd.
Références
Zhou W, Håkansson K. Structural characterization of carbohydrates by Fourier transform tandem mass spectrometry. Curr Proteomics. 2011;8(4):297-308. doi:10.2174/157016411798220826
Jaiswal R, Kuhnert N. Identification and characterization of the phenolic glycosides of Lagenaria Siceraria Stand. (bottle gourd) fruit by liquid chromatography-tandem mass spectrometry. J Agric Food Chem. 2014;62(6):1261-1271. doi:10.1021/jf4053989
Bertozzi CR, Kiessling LL. Chemical glycobiology. Science (80-). 2001;291(5512):2357-2364. doi:10.1126/science.1059820
Dwek RA. Glycobiology: toward understanding the function of sugars. Chem Rev. 1996;96(2):683-720. doi:10.1021/cr940283b
Cancilla MT, Wong AW, Voss LR, Lebrilla CB. Fragmentation reactions in the mass spectrometry analysis of neutral oligosaccharides. Anal Chem. 1999;71(15):3206-3218. doi:10.1021/ac9813484
Zaia J. Mass spectrometry of oligosaccharides. Mass Spectrom Rev. 2004;23(3):161-227. doi:10.1002/mas.10073
Deshpande S, Matei MF, Jaiswal R, Bassil BS, Kortz U, Kuhnert N. Synthesis, structure, and tandem mass spectrometric characterization of the diastereomers of quinic acid. J Agric Food Chem. 2016;64(38):7298-7306. doi:10.1021/acs.jafc.6b02472
Jaiswal R, Matei M, Glembockyte V, Patras M, Kuhnert N. Hierarchical key for the LC-MSn identification of all ten regio- and stereoisomers of caffeoylglucose. J Agric Food Chem. 62(38):9252-9265. doi:10.1021/jf501210s
Jaiswal R, Kuhnert N. Hierarchical scheme for liquid chromatography/multi-stage spectrometric identification of 3,4,5-triacyl chlorogenic acids in green robusta coffee beans. Rapid Commun Mass Spectrom. 2010;24(15):2283-2294. doi:10.1002/rcm.4639
Clifford MN, Knight S, Kuhnert N. Discriminating between the six isomers of dicaffeoylquinic acid by LC-MSN. J Agric Food Chem. 2005;53(10):3821-3832. doi:10.1021/jf050046h
Jaiswal R, Matei MF, Ullrich F, Kuhnert N. How to distinguish between cinnamoylshikimate esters and chlorogenic acid lactones by liquid chromatography-tandem mass spectrometry. J Mass Spectrom. 2011;46(9):933-942. doi:10.1002/jms.1972
Kuhnert N, Jaiswal R, Sovdat T, Vivan F. Profiling and characterization by LC-MS n of the chlorogenic acids and hydroxycinnamoylshikimate esters in mate (Ilex paraguariensis). J Agric Food Chem. 58(9):5471-5484. doi:10.1021/jf904537z
Gray CJ, Schindler B, Migas LG, et al. Bottom-up elucidation of glycosidic bond stereochemistry. Anal Chem. 2017;89(8):4540-4549. doi:10.1021/acs.analchem.6b04998
Ashline D, Singh S, Hanneman A, Reinhold V. Congruent strategies for carbohydrate sequencing. 1. Mining structural details by MSn. Anal Chem. 2005;77(19):6250-6262. doi:10.1021/ac050724z
Megías-Pérez R, Ruiz-Matute AI, Corno M, Kuhnert N. Analysis of minor low molecular weight carbohydrates in cocoa beans by chromatographic techniques coupled to mass spectrometry. J Chromatogr A. 2019;1584:135-143. doi:10.1016/j.chroma.2018.11.033
Duus JØ, Gotfredsen CH, Bock K. Carbohydrate structural determination by NMR spectroscopy: modern methods and limitations. Chem Rev. 2000;100(12):4589-4614. doi:10.1021/cr990302n
Taylor VF, March RE, Longerich HP, Stadey CJ. A mass spectrometric study of glucose, sucrose, and fructose using an inductively coupled plasma and electrospray ionization. Int J Mass Spectrom. 2005;243(1):71-84. doi:10.1016/j.ijms.2005.01.001
Major M, Fouquet T, Charles L. Isomeric distinction of small oligosaccharides: a bottom-up approach using the kinetic method. J Am Soc Mass Spectrom. 2011;22(7):1252-1259. doi:10.1007/s13361-011-0128-6
Hill HH, Bendiak B, Clowers B, Zhu M. Ion mobility-mass spectrometry analysis of isomeric carbohydrate precursor ions. Anal Bioanal Chem. 2009;394(7):1853-1867. doi:10.1007/s00216-009-2865-y
Polfer NC, Valle JJ, Moore DT, Oomens J, Eyler JR, Bendiak B. Differentiation of isomers by wavelength-tunable infrared multiple-photon dissociation-mass spectrometry: application to glucose-containing disaccharides. Anal Chem. 2006;78(3):670-679. doi:10.1021/ac0519458
Hofmann J, Hahm HS, Seeberger PH, Pagel K. Identification of carbohydrate anomers using ion mobility-mass spectrometry. Nature. 2015;526(7572):241-244. doi:10.1038/nature15388
Schindler B, Barnes L, Renois G, et al. Anomeric memory of the glycosidic bond upon fragmentation and its consequences for carbohydrate sequencing. Nat Commun. 2017;8(1):973. doi:10.1038/s41467-017-01179-y
Mulroney B, Peel JB, Traeger JC. Relative gas-phase acidities of glucopyranose from molecular orbital calculations. J Mass Spectrom. 1999;34(5):544-553. doi:10.1002/(sici)1096-9888(199905)34:5%3C544::aid-jms807%3E3.0.co;2-m
Gao Q, Nilsson U, Ilag LL, Leck C. Monosaccharide compositional analysis of marine polysaccharides by hydrophilic interaction liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem. 2011;399(7):2517-2529. doi:10.1007/s00216-010-4638-z
Carlesso V, Fournier F, Tabet J-C. Stereochemical differentiation of four monosaccharides using transition metal complexes by electrospray ionization/ion-trap mass spectrometry. Eur J Mass Spectrom. 2000;6(5):421-428. doi:10.1255/ejms.365
Paine JB III, Pithawalla YB, Naworal JD, Thomas CE Jr. Carbohydrate pyrolysis mechanisms from isotopic labeling. Part 1: the pyrolysis of glycerin: discovery of competing fragmentation mechanisms affording acetaldehyde and formaldehyde and the implications for carbohydrate pyrolysis. J Anal Appl Pyrolysis. 2007;80(2):297-311. doi:10.1016/j.jaap.2007.03.007
Dallinga JW, Heerma W. Reaction mechanism and fragment ion structure determination of deprotonated small oligosaccharides, studied by negative ion fast atom bombardment (tandem) mass spectrometry. Biol Mass Spectrom. 1991;20(4):215-231. doi:10.1002/bms.1200200410
Angyal SJ. Composition and conformation of sugars in solution. Angew Chemie-International Ed. 1969;8(3):157. doi:10.1002/anie.196901571
Hernandez J, Müller A, Jaiswal R, Davalos JZ, Kuhnert N. Energy resolved mass spectrometry of chlorogenic acids and its application to isomer quantification by direct infusion tandem mass spectrometry. Phytochem Anal. 2018;29(4):406-412. doi:10.1002/pca.2770
Golon A, González F, Dávalos J, Kuhnert N. Investigating the thermal decomposition of starch and cellulose in model systems and toasted bread using domino tandem mass spectrometry. J Agric Food Chem. 61(3):674-684. doi:10.1021/jf302135k
Ma PH, Sugita K, Arai S. 13C-selective two-stage IRMPD of mixtures of CHClF2 and HI. Appl Phys B Photophysics Laser Chem. 1990;50(5):385-392. doi:10.1007/BF00325091
Domon B, Costello CE. A systematic nomenclature for carbohydrate fragmentations in fab-Ms Ms spectra of glycoconjugates. Glycoconj J. 1988;5(4):397-409. doi:10.1007/bf01049915
Boyd R, Somogyi Á. The mobile proton hypothesis in fragmentation of protonated peptides: a perspective. J am Soc Mass Spectrom. 2010;21(8):1275-1278. doi:10.1016/j.jasms.2010.04.017
Wysocki VH, Tsaprailis G, Smith LL, Breci LA. Mobile and localized protons: a framework for understanding peptide dissociation. J Mass Spectrom. 2000;35(12):1399-1406. doi:10.1002/1096-9888(200012)35:12%3C1399::AID-JMS86%3E3.0.CO;2-R
Salpin J-Y, Tortajada J. Gas-phase acidity of D-glucose. A density functional theory study. J Mass Spectrom. 2004;39(8):930-941. doi:10.1002/jms.671
Bythell BJ, Rabus JM, Wagoner AR, Abutokaikah MT, Maître P. Sequence ion structures and dissociation chemistry of deprotonated sucrose anions. J Am Soc Mass Spectrom. 2018;29(12):2380-2393. doi:10.1007/s13361-018-2065-0