Cryogenic Vibrational Spectroscopy Provides Unique Fingerprints for Glycan Identification
Tóm tắt
The structural characterization of glycans by mass spectrometry is particularly challenging. This is because of the high degree of isomerism in which glycans of the same mass can differ in their stereochemistry, attachment points, and degree of branching. Here we show that the addition of cryogenic vibrational spectroscopy to mass and mobility measurements allows one to uniquely identify and characterize these complex biopolymers. We investigate six disaccharide isomers that differ in their stereochemistry, attachment point of the glycosidic bond, and monosaccharide content, and demonstrate that we can identify each one unambiguously. Even disaccharides that differ by a single stereogenic center or in the monosaccharide sequence order show distinct vibrational fingerprints that would clearly allow their identification in a mixture, which is not possible by ion mobility spectrometry/mass spectrometry alone. Moreover, this technique can be applied to larger glycans, which we demonstrate by distinguishing isomeric branched and linear pentasaccharides. The creation of a database containing mass, collision cross section, and vibrational fingerprint measurements for glycan standards should allow unambiguous identification and characterization of these biopolymers in mixtures, providing an enabling technology for all fields of glycoscience.
Tài liệu tham khảo
Varki A, Cummings R.D., Esko J.D., Freeze H.H., Stanley P., Bertozzi C.R., Hart G.W., Etzler M.E. (eds.): Essentials of Glycobiology, 2nd edn. Cold Spring Harbor Laboratory Press, Cold Spring Harbor (2009)
National Research Council. 2012. Transforming Glycoscience: A Roadmap for the Future. Washington, DC: The National Academies Press. doi:10.17226/13446.
Varki, A.: Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 3, 97–130 (1993)
Hounsell, E.F., Davies, M.J., Renouf, D.V.: O-linked protein glycosylation structure and function. Glycoconj. J. 13, 19–26 (1996)
Dennis, J.W., Granovsky, M., Warren, C.E.: Protein glycosylation in development and disease. Bioessays 21, 412–421 (1999)
Han, L., Costello, C.E.: Mass spectrometry of glycans. Biochemistry (Moscow) 78(710–720) (2013)
Yu, X., Jiang, Y., Chen, Y., Huang, Y., Costello, C.E., Lin, C.: Detailed glycan structural characterization by electronic excitation dissociation. Anal. Chem. 85, 10017–10021 (2013)
Han, L., Costello, C.E.: Electron transfer dissociation of milk oligosaccharides. J. Am. Soc. Mass Spectrom. 22, 997–1013 (2011)
Ren, R., Hong, Z., Gong, H., Laporte, K., Skinner, M., Seldin, D.C., Costello, C.E., Connors, L.H., Trinkaus-Randall, V.: Role of glycosaminoglycan sulfation in the formation of immunoglobulin light chain amyloid oligomers and fibrils. J. Biol. Chem. 285, 37672–37682 (2010)
Kailemia, M.J., Ruhaak, L.R., Lebrilla, C.B., Amster, I.J.: Oligosaccharide analysis by mass spectrometry: a review of recent developments. Anal. Chem. 86, 196–212 (2014)
Hofmann, J., Hahm, H.S., Seeberger, P.H., Pagel, K.: Identification of carbohydrate anomers using ion mobility-mass spectrometry. Nature 526, 241–244 (2015)
Pagel, K., Harvey, D.J.: Ion mobility-mass spectrometry of complex carbohydrates: collision cross sections of sodiated N-linked glycans. Anal. Chem. 85, 5138–5145 (2013)
Gaye, M.M., Kurulugama, R., Clemmer, D.E.: Investigating carbohydrate isomers by IMS-CID-IMS-MS: precursor and fragment ion cross-sections. Analyst 140, 6922–6932 (2015)
Gaye, M.M., Nagy, G., Clemmer, D.E., Pohl, N.L.: Multidimensional analysis of 16 glucose isomers by ion mobility spectrometry. Anal. Chem. 88, 2335–2344 (2016)
Isailovic, D., Plasencia, M.D., Gaye, M.M., Stokes, S.T., Kurulugama, R.T., Pungpapong, V., Zhang, M., Kyselova, Z., Goldman, R., Mechref, Y., Novotny, M.V., Clemmer, D.E.: Delineating diseases by IMS-MS profiling of serum N-linked glycans. J. Proteome Res. 11, 576–585 (2012)
Zhu, F., Lee, S., Valentine, S.J., Reilly, J.P., Clemmer, D.E.: Mannose7 glycan isomer characterization by IMS-MS/MS analysis. J. Am. Soc. Mass Spectrom. 23, 2158–2166 (2012)
Seo, Y., Andaya, A., Leary, J.A.: Preparation, separation, and conformational analysis of differentially sulfated heparin octasaccharide isomers using ion mobility mass spectrometry. Anal. Chem. 84, 2416–2423 (2012)
Both, P., Green, A.P., Gray, C.J., Sardzik, R., Voglmeir, J., Fontana, C., Austeri, M., Rejzek, M., Richardson, D., Field, R.A., Widmalm, G., Flitsch, S.L., Eyers, C.E.: Discrimination of epimeric glycans and glycopeptides using IM-MS and its potential for carbohydrate sequencing. Nat. Chem. 6, 65–74 (2014)
Williams, J.P., Grabenauer, M., Holland, R.J., Carpenter, C.J., Wormald, M.R., Giles, K., Harvey, D.J., Bateman, R.H., Scrivens, J.H., Bowers, M.T.: Characterization of simple isomeric oligosaccharides and the rapid separation of glycan mixtures by ion mobility mass spectrometry. Int. J. Mass. Spectrom. 298, 119–127 (2010)
Fenn, L.S., McLean, J.A.: Structural resolution of carbohydrate positional and structural isomers based on gas-phase ion mobility-mass spectrometry. Phys. Chem. Chem. Phys. 13, 2196–2205 (2011)
Zhu, M., Bendiak, B., Clowers, B., Hill Jr., H.H.: Ion mobility-mass spectrometry analysis of isomeric carbohydrate precursor ions. Anal. Bioanal. Chem. 394, 1853–1867 (2009)
Masson, A., Kamrath, M.Z., Perez, M.A., Glover, M.S., Rothlisberger, U., Clemmer, D.E., Rizzo, T.R.: Infrared spectroscopy of mobility-selected H+-Gly-Pro-Gly-Gly (GPGG). J. Am. Soc. Mass Spectrom. 26, 1444–1454 (2015)
Hernandez, O., Isenberg, S., Steinmetz, V., Glish, G.L., Maitre, P.: Probing mobility-selected saccharide isomers: selective ion-molecule reactions and wavelength-specific IR activation. J. Phys. Chem. A 119, 6057–6064 (2015)
Polfer, N.C., Valle, J.J., Moore, D.T., Oomens, J., Eyler, J.R., Bendiak, B.: Differentiation of isomers by wavelength-tunable infrared multiple-photon dissociation-mass spectrometry: application to glucose-containing disaccharides. Anal. Chem. 78, 670–679 (2006)
Tan, Y.L., Polfer, N.C.: Linkage and anomeric differentiation in trisaccharides by sequential fragmentation and variable-wavelength infrared photodissociation. J. Am. Soc. Mass Spectrom. 26, 359–368 (2015)
Gray, C.J., Schindler, B., Migas, L.G., Pičmanová, M., Allouche, A.R., Green, A.P., Mandal, S., Motawia, M.S., Sánchez-Pérez, R., Bjarnholt, N., Møller, B.L., Rijs, A.M., Barran, P.E., Compagnon, I., Eyers, C.E., Flitsch, S.L.: Bottom-up elucidation of glycosidic bond stereochemistry. Anal. Chem. 89, 4540–4549 (2017)
Schindler, B., Barnes, L., Gray, C.J., Chambert, S., Flitsch, S.L., Oomens, J., Daniel, R., Allouche, A.R., Compagnon, I.: IRMPD spectroscopy sheds new (infrared) light on the sulfate pattern of carbohydrates. J. Phys. Chem. A 121, 2114–2120 (2017)
Mucha, E., González Flórez, A.I., Marianski, M., Thomas, D.A., Hoffmann, W., Struwe, W.B., Hahm, H.S., Gewinner, S., Schöllkopf, W., Seeberger, P.H., von Helden, G., Pagel, K.: Glycan fingerprinting using cold-ion infrared spectroscopy. Angew. Chem. Int. Ed. (2017). doi:10.1002/anie.201702896
Kamrath, M.Z., Garand, E., Jordan, P.A., Leavitt, C.M., Wolk, A.B., Van Stipdonk, M.J., Miller, S.J., Johnson, M.A.: Vibrational characterization of simple peptides using cryogenic infrared photodissociation of H2-tagged, mass-selected ions. J. Am. Chem. Soc. 133, 6440–6448 (2011)
Pierson, N.A., Valentine, S.J., Clemmer, D.E.: Evidence for a quasi-equilibrium distribution of states for bradykinin [M + 3H]3+ ions in the gas phase. J. Phys. Chem. B. 114, 7777–7783 (2010)
Papadopoulos, G., Svendsen, A., Boyarkin, O.V., Rizzo, T.R.: Conformational distribution of bradykinin [bk+2 H]2+ revealed by cold ion spectroscopy coupled with FAIMS. J. Am. Soc. Mass Spectrom. 23, 1173–1181 (2012)
Rizzo, T.R., Stearns, J.A., Boyarkin, O.V.: Spectroscopic studies of cold, gas-phase biomolecular ions. Int. Rev. Phys. Chem. 28, 481–515 (2009)
Stearns, J.A., Seaiby, C., Boyarkin, O.V., Rizzo, T.R.: Spectroscopy and conformational preferences of gas-phase helices. Phys. Chem. Chem. Phys. 11, 125–132 (2009)
Harvey, D.J., Merry, A.H., Royle, L., Campbell, M.P., Dwek, R.A., Rudd, P.M.: Proposal for a standard system for drawing structural diagrams of N- and O-linked carbohydrates and related compounds. Proteomics 9, 3796–3801 (2009)
Marino, K., Bones, J., Kattla, J.J., Rudd, P.M.: A systematic approach to protein glycosylation analysis: a path through the maze. Nat. Chem. Biol. 6, 713–723 (2010)