Diastereomeric resolution directed towards chirality determination focussing on gas-phase energetics of coordinated sodium dissociation

Scientific Reports

Volumn 6, Issue , 2016, Pages

  Kanie, Osamu ^a,d   Shioiri, Yuki ^b,c   Ogata, Koji ^c   Uchida, Waka ^b,c   Daikoku, Shusaku ^d   Suzuki, Katsuhiko ^d   Nakamura, Shinichiro ^c,e   Ito, Yukishige ^c,d  

^a TOKAI UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c RIKEN   (Japan)

^d JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^e Advanced Center for Computing and Communication   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84962429835     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep24005     Document Type: Article

References (34)

1. Vincent, F. et al. Crystal structures of bovine odorant-binding protein in complex with odorant molecules. Eur. J. Biochem. 271, 3832-3842 (2004).
2. Bohbot, J. D. & Dickens, J. C. Characterization of an enantioselective odorant receptor in the yellow fever mosquito Aedes aegypti. PLoS ONE. 4, e7032 (2009).
3. Aebersold, R. & Goodlett, D. R. Mass spectrometry in proteomics. Chem. Rev. 101, 269-295 (2001).
4. Zaia, J. Mass spectrometry of oligosaccharides. Mass Spectrom. Rev. 23, 161-227 (2004).
5. Bijvoet, J. M., Peerdeman, A. F. & Van Bommel, A. J. Determination of the absolute configuration of optically active compounds by means of X-rays. Nature. 168, 271-272 (1951).
6. Pitzer, M. et al. Direct determination of absolute molecular stereochemistry in gas phase by Coulomb explosion imaging. Science. 341, 1096-1100 (2013).
7. Ward, T. J. & Baker, B. A. Chiral separations. Anal. Chem. 80, 4363-4372 (2008).
8. Dale, J. A. & Mosher, H. S. Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J. Am. Chem. Soc. 95, 512-519 (1973).
9. Sawada, M. et al. Enantioselective complexation of carbohydrate or crown ether hosts with organic ammonium ion guests detected by FAB mass spectrometry. J. Am. Chem. Soc. 115, 7381-7388 (1993).
10. Shen, W. Y., Wong, P. S. H. & Cooks, R. G. Stereoisomeric distinction by the kinetic method: 2,3-butanediol. Rapid Commun. Mass Spectrom. 11, 71-74 (1997).
11. Vekey, K. & Czira, G. Distinction of amino acid enantiomers based on the basicity of their dimers. Anal. Chem. 69, 1700-1705 (1997).
12. Dearden, D. V., Dejsupa, C., Liang, Y., Bradshaw, J. S. & Izatt, R. M. Intrinsic contributions to chiral recognition: discrimination between enantiomeric amines by dimethyldiketopyridino-18-crown-6 in the gas phase. J. Am. Chem. Soc. 119, 353-359 (1997).
13. Yao, Z.-P., Wan, T. S. M., Kwong, K.-P. & Che, C.-T. Chiral analysis by electrospray ionization mass spectrometry/mass spectrometry. 1. Chiral recognition of 19 common amino acids. Anal. Chem. 72, 5383-5393 (2000).
14. Paladini, A. et al. Enantiodiscrimination of chiral α-aminophosphonic acids by mass spectrometry. Chirality. 13, 707-711 (2001).
15. Ahn, S., Ramirez, J., Grigorean, G. & Lebrilla, C. B. Chiral recognition in gas-phase cyclodextrin: amino acid complexes - is the three point interaction still valid in the gas phase? J. Am. Soc. Mass Spectrom. 12, 278-287 (2001).
16. Mancel, V., Sellier, N., Lesage, D., Fournier, F. & Tabet, J.-C. Gas phase enantiomeric distinction of (R)-and (S)-aromatic hydroxy esters by negative ion chemical ionization mass spectrometry using a chiral reagent gas. Int. J. Mass Spectrom. 237, 185-195 (2004).
17. Bagheri, H., Chen, H. & Cooks, R. G. Chiral recognition by proton transfer reactions with optically active amines and alcohols. Chem. Commun. 2740-2741 (2004). doi: 10.1039/B410882E.
18. Grigorean, G., Cong, X. & Lebrilla, C. B. Chiral analyses of peptides by ion/molecule reactions. Int. J. Mass Spectrom. 234, 71-77 (2004).
19. Enders, J. R. & Mclean, J. A. Chiral and structural analysis of biomolecules using mass spectrometry and ion mobility-mass spectrometry. Chirality. 21, E253-E264 (2009).
20. Reddy, P. N. et al. Differentiation of Boc-α ,β-and β ,α-peptides and a pair of diastereomeric β ,α-dipeptides by positive and negative ion electrospray tandem mass spectrometry (ESI-MS/MS). J. Mass Spectrom. 40, 1429-1438 (2005).
21. Tsunematsu, H. et al. Differentiation of a pair of diastereomeric tertiarybutoxycarbonylprolylproline ethyl esters by collisioninduced dissociation of sodium adduct ions in electrospray ionization mass spectrometry and evidence for chiral recognition by ab initio molecular orbital calculations. J. Mass Spectrom. 38, 188-195 (2003).
22. Sun, C., Zhu, P., Hu, N., Wang, D. & Pan, Y. Differentiation of lisinopril and its RSS diastereomer by liquid chromatography combined with collision-induced dissociation mass spectrometry. J. Mass. Spectrom. 45, 89-96 (2010).
23. Lagarrigue, M. et al. Diastereomeric differentiation of peptides with CuII and FeII complexation in an ion trap mass spectrometer. J. Mass Spectrom. 41, 1073-1085 (2006).
24. Cheng, M. T., Barbalas, M. P., Pegues, R. F. & McLafferty, F. W. Tandem mass spectrometry: structural and stereochemical information from steroids. J. Am. Chem. Soc. 105, 1510-1513 (1983).
25. Kenttamaa, H. I. & Cooks, R. G. Tautomer characterization by energy resolved mass spectrometry. Dimethyl phosphite and dimethyl phosphonate ions. J. Am. Chem. Soc. 107, 1881-1886 (1985).
26. Laprévote, O., Ducrot, P., Thal, C., Serani, L. & Das, B. C. Stereochemistry of electrosprayed ions. Indoloquinolizidine derivatives. J. Mass Spectrometry, 31, 1149-1155 (1996).
27. Carlesso, V., Afonso, C., Fournier, F. & Tabet, J. C. Stereochemical effects from doubly-charged iron clusters for the structural elucidation of diastereomeric monosaccharides using ESI/IT-MS. Int. J. Mass Spectrom. 219, 559-575 (2002).
28. Nagy, T. et al. Chiral differentiation of the noscapine and hydrastine stereoisomers by electrospray ionization tendem mass spectrometry. J. Mass Spectrom. 50, 240-246 (2015).
29. Daikoku, S., Ako, T., Kato, R., Ohtsuka, I. & Kanie, O. Discrimination of 16 structural isomers of fucosyl galactoside based on energy-resolved mass spectrometry. J. Am. Soc. Mass Spectrom. 18, 1873-1879 (2007).
30. Kurimoto, A., Daikoku, S., Mutsuga, S. & Kanie, O. Analysis of energy-resolved mass spectra at MSn in a pursuit to characterize structural isomers of oligosaccharides. Anal Chem. 78, 3461-3466 (2006).
31. Kanie, O. et al. Analysis of behavior of sodiated sugar hemiacetals under low-energy collision-induced dissociation conditions and application to investigating mutarotation and mechanism of a glycosidase. Proc. Jpn Acad., Ser. B. 85, 204-215 (2009).
32. Bothner, B., Carmitchel, L., Staniszewski, K., Sonderegger, M. & Siuzdak, G. Biomolecule structure characterization in the gas phase using mass spectrometry. Spectroscopy 16, 71-79 (2002).
33. Cancilla, M. T., Wong, A. W., Voss, L. R. & Lebrilla, C. B. Fragmentation Reactions in the Mass Spectrometry Analysis of Neutral Oligosaccharides. Anal. Chem. 71, 3206-3218 (1999).
34. Harvey, D. J. Electrospray mass spectrometry and fragmentation of N-linked carbohydrates derivatized at the reducing terminus. J. Am. Soc. Mass Spectrom. 11, 900-915 (2000).