Chiral recognition detected by fast atom bombardment mass spectrometry

Mass Spectrometry Reviews

Volumn 16, Issue 2, 1997, Pages 73-90

  Sawada, Masami ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; CARBOHYDRATE; ETHER DERIVATIVE; ION; METAL;

CHEMISTRY; DIMERIZATION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; METHODOLOGY; REVIEW; STEREOISOMERISM;

ANTI-BACTERIAL AGENTS; CARBOHYDRATES; DIMERIZATION; ETHERS; IONS; METALS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; STEREOISOMERISM;

EID: 0031083250     PISSN: 02777037     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2787(1997)16:2<73::AID-MAS2>3.0.CO;2-6     Document Type: Article

References (47)

1. Arnett, E. M.; Zingg, S. P. "Chiral discrimination in the energetics of ion aggregation," J. Am. Chem. Soc. 1981, 103, 1221-1222.
2. Baldwin, M. A.; Howell, S. A.; Welham, K. J.; Winkler, F. J. "Identification of chiral isomers by fast atom bombardment/mass spectrometry: dialkyl tartrates," Biomed. Environ. Mass Spectrom. 1988, 16, 357-360.
3. Boss, R. D.; Popov, A. I. "A competitive NMR technique for measurements of metal ion-macrocyclic polyether complexation constants in solutions," Inorg. Chem. 1985, 24, 3660-3664.
4. Chen, Y.-Z.; Li, H.; Yang, H.-J.; Hua, S.-M.; Li, H.-Q.; Zhao, F.-Z.; Chen, N.-Y. "Stereochemical effects in mass spectrometry 7. Determination of absolute configuration of some organic molecules by reaction mass spectrometry," Org. Mass Spectrom. 1988, 23, 821-824.
5. Chu, I.-H.; Dearden, D. V.; Bradshaw, J. S.; Huszthy, P.; Izatt, R. M. "Chiral host-guest recognition in an ion-molecule reaction," J. Am. Chem. Soc. 1993, 115, 4318-4320.
6. Cram, D. J. "The design of molecular hosts, guests, and f their complexes (Nobel Lecture)," Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020.
7. Dang, T. T.; Pedersen, S. F.; Leary, J. A. "Chiral recognition in the gas phase: mass spectrometric studies of diastereomeric cobalt complexes," J. Am. Soc. Mass Spectrom. 1994, 5, 452-459.
8. Dearden, D. V. "Host-guest molecular recognition without solvents." In Physical Supramolecular Chemistry, Echegoyen, L.; Kaifer, A. E. Eds.; Kluwer Academic Publishers: Dordrecht, 1996, 229-247.
9. Drabowicz, J.; Dudzinski, B.; Mitotajczyk, M.; Sochacki, M. "A study of β-cyclodextrin inclusion complexes with optically active alkyl p-tolyl sulfoxides by fast atom bombardment mass spectrometry," Polish J. Chem. 1994, 68, 2265-2270.
10. Easton, C. J.; Lincoln, S. F. "Chiral discrimination by modified cyclodextrins," Chem. Soc. Rev. 1996, 163-170.
11. Fales, H. M.; Wright, G. J. "Detection of chirality with the chemical ionization mass spectrometer. 'Meso' ions in the gas phase," J. Am. Chem. Soc. 1977, 99, 2339-2340.
12. Hashimoto, K.; Sumida, Y.; Terada, S.; Okamura, K. "Chiral recognition by atmospheric pressure chemical ionization mass spectrometry," J. Mass Spectrom. Soc. Jpn. 1993a, 41, 87-94.
13. Hashimoto, K.; Sumida, Y.; Terada, S.; Okamura, K. "Stereochemical effects in chemical ionization mass spectrometry using chiral reagent gases," J. Mass Spectrom. Soc. Jpn. 1993b, 47, 95-100.
14. Haskins, N. J.; Saunders, M. R.; Camilleri, P. "The complexation and chiral selectivity of 2-hydroxypropyl-β-cyclodextrin with guest molecules as studied by electrospray mass spectrometry," Rapid Commun. Mass Spectrom. 1994, 8, 423-426.
15. Hofmeister, G.; Leary, J. A. "Chiral recognition of lithium-coordinated diols using tandem mass spectrometry," Org. Mass Spectrom. 1991, 26, 811-812.
16. Hua, S.; Chen, Y.; Jiang, L.; Xue, S. "Stereochemical effects in mass spectrometry 3. Detection of chirality by chemical ionization mass spectrometry," Org. Mass Spectrom. 1986, 21, 7-10.
17. Kalman, J. R.; Williams, D. H. "An NMR study of the interaction between the antibiotic ristocetin A and a cell wall peptide analogue. Negative nuclear overhauser effects in the investigation of drug binding sites," J. Am. Chem. Soc. 1980, 102, 906-912.
18. Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. "Self and nonself recognition of asymmetric catalysts. Nonlinear effects in the amino alcohol-promoted enantioselective addition of dialkylzincs to aldehydes," J. Am. Chem. Soc. 1995, 117, 4832-4842.
19. Lim, H.-K.; Hsieh, Y. L.; Ganem, B.; Henion, J. "Recognition of cell-wall peptide ligands by vancomycin group antibiotics: studies using ion spray mass spectrometry," J. Mass Spectrom. 1995, 30, 708-714.
20. Martens, J.; Lübben, S.; Schwarting, W. "Stereoselective reaction mass spectrometry with cyclic α-amino acids," Z. Naturforsch 1991, 46b, 320-325.
21. Mikojajczyk, M.; Drabowicz, J. "Optical resolution of chiral sulfinyl compounds via β-cyclodextrin inclusion complexes," J. Am. Chem. Soc. 1978, 100, 2510-2515.
22. Okamura, K.; Sumida, Y.; Fujiwara, Y.; Terada, S.; Kim, H.; Hashimoto, K. "Chiral recognition in high performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry," J. Mass Spectrom. Soc. Jpn. 1995, 43, 97-105.
23. Nikolaev, E. N.; Goginashvili, G. T.; Tal'rose, V. L.; Kostyanovsky, R. G. "Investigation of asymmetric gas-phase ion/ molecule reactions by FT-ICR spectrometry," Int. J. Mass Spectrom. Ion Process 1988, 86, 249-252.
24. Pócsfalvi, G.; Lipták, M.; Huszthy, P.; Bradshaw, J. S.; Izatt, R. M.; Vékey, K. "Characterization of chiral host-guest complexation in fast atom bombardment mass spectrometry," Anal. Chem. 1996, 68, 792-795.
25. Sawada, M. "Chiral mass spectrometry." In Biological Mass Spectrometry. Present and Future, Matsuo, T.; Caprioli, R. M.; Gross, M. L.; Seyama, Y., Eds.; John Wiley and Sons: Chichester, 1994, Chapter 3.19, 639-646.
26. Sawada, M. "Advances in the application of FAB mass spectrometry to studies on chiral recognition of chiral crown ethers," Dojin News 1996, 78, 10-17.
27. Sawada, M. "Chiral recognition in host-guest complexation determined by FAB mass spectrometry," J. Mass Spectrom. Soc. Jpn. 1997, 45, 439-458.
28. Sawada, M.; Okumura, Y.; Yamada, H.; Takai, Y.; Takahashi, S.; Kaneda, T.; Hirose, K.; Misumi, S. "Cross-chiral examinations of molecular enantioselective recognition by fast atom bombardment mass spectrometry: host-guest complexations between chiral crown ethers and chiral organic ammonium ions," Org. Mass Spectrom. 1993b, 28, 1525-1528.
29. Sawada, M.; Okumura, Y.; Shizuma, M.; Takai, Y.; Hidaka, Y.; Yamada, H.; Tanaka, T.; Kaneda, T.; Hirose, K.; Misumi, S.; Takahashi, S. "Enantioselective complexation of carbohydrate or crown ether hosts with organic ammonium ion guests detected by FAB mass spectrometry," J. Am. Chem. Soc. 1993a, 115, 7381-7388.
30. Sawada, M.; Ouyang, L.; Takai, Y.; Yamada, H.; Hanafusa, T. "Complexation between saccharide and ammonium ion in gas phase. Regarding stereochemical effects of methoxy groups at permethylated monosaccharides on stabilities of cluster ions in FAB mass spectrometry," Chem. Lett. 1989, 1743-1746.
31. Sawada, M.; Ouyang, L.; Takai, Y.; Yamada, H.; Hanafusa, T.; Kinoshita, T.; Mochizuki, T. "Complexation between monosaccharide and potassium ion in gas phase. A correlation between relative FABMS peak-intensities and gas phase stabilities of the cluster ions," Chem. Lett. 1990, 1361-1364.
32. Sawada, M.; Ouyang, L.; Takai, Y.; Yamada, H.; Shizuma, M.; Kinoshita, T.; Mochizuki, T.; Hanafusa, T. "1:1 Adduct ion formation of permethylated monosaccharides with organic cations in FAB mass spectrometry," Bull. Chem. Soc. Jpn. 1991, 64, 1243-1252.
33. Sawada, M.; Shizuma, M.; Takai, Y.; Yamada, H.; Tanaka, T.; Okumura, Y.; Hidaka, Y.; Hanafusa, T.; Takahashi, S. "1:1 Adduct ion formation of simple carbohydrate derivatives with cations using FAB mass spectrometry. Comparison of O-acetyl, N-butyl, and O-methyl modifications," Bull. Chem. Soc. Jpn. 1992, 65, 1275-1279.
34. Sawada, M.; Shizuma, M.; Takai, Y.; Yamada, H.; Kaneda, T.; Hanafusa, T. "Enantioselectivity in FAB mass spectrometry," J. Am. Chem. Soc. 1992, 114, 4405-4406.
35. Sawada, M.; Takai, Y.; Yamada, H.; Kaneda, T.; Kamada, K.; Mizooku, T.; Hirose, K.; Tobe, Y.; Naemura, K. "Chiral recognition in molecular complexation for the crown etheramino ester system. A facile FAB mass spectrometric approach," J. Chem. Soc., Chem. Commun. 1994, 2497-2498.
36. Sawada, M.; Takai, Y.; Yamada, H.; Hirayama, S.; Kaneda, T.; Tanaka, T.; Kamada, K.; Mizooku, T.; Takeuchi, S.; Ueno, K.; Hirose, K.; Tobe, Y.; Naemura, K. "Chiral recognition in host-guest complexation determined by the enantiomer-labeled guest method using fast atom bombardment mass spectrometry," J. Am. Chem. Soc. 1995, 117, 7726-7736.
37. Sawada, M.; Takai, Y.; Kaneda, T.; Arakawa, R.; Okamoto, M.; Doe, H.; Matsuo, T.; Naemura, K.; Hirose, K.; Tobe, Y. "Chiral molecular recognition in electrospray ionization mass spectrometry," Chem. Commun. 1996, 1735-1736.
38. Schneider, H.-J. "Mechanisms of molecular recognition: investigations of organic host-guest complexes," Angew. Chem. Int. Ed. Engl. 1991, 30, 1417-1436.
39. Tabet, J. C. "Ion-molecule reactions in the gas phase. IX. Differentiation of enantiomeric menthols using a stereospecific SN2 process induced by a chiral reagent," Tetrahedron 1987, 43, 3413-3420.
40. Tsukube, H.; Sohmiya, H. "Chiral recognition of asymmetric amine salts by chemically modified polyether antibiotics," J. Org. Chem. 1991, 56, 875-878.
41. Webb, T. H.; Wilcox, C. S. "Enantioselective and diastereo-selective molecular recognition of neutral molecules," Chem. Soc. Rev. 1993, 383-395.
42. Williams, D. H.; Bradley, C.; Bojesen, G.; Shantikarn, S.; Taylor, L. C. E. "Fast atom bombardment mass spectrometry: a powerful technique for the study of polar molecules," J. Am. Chem. Soc. 1981, 103, 5700-5704.
43. Winkler, F. J.; Medina, R.; Winkler, J.; Krause, H. "Mass spectral and semi-empirical studies on chiral discrimination in gaseous aggregation products of protonated didalkyl tartrates," J. Chromatogr. A 1994, 666, 549-556.
44. Winkler, F. J.; Splitter, J. S. "Stereochemical effects in the positive- and negative-ion chemical-ionization mass spectra of stereoisomeric molecules." In Applications of Mass Spectrometry to Organic Stereochemistry, Splitter, J. S.; Turecek, F., Eds.; VCH Publishers: New York, 1994, Chapter 16, 353-370.
45. Winkler, F. J.; Stahl, D.; Maquin, F. "Chirality effects in the chemical ionization mass spectra of dialkyl tartrates," Tetrahedron Lett. 1986, 27, 335-338.
46. Yang, H.-J.; Chen, Y.-Z. "Stereochemical effects in mass spectrometry XIII. Determination of absolute configuration by fast atom bombardment mass spectrometry," Org. Mass Spectrom. 1992, 27, 736-740.
47. Zingg, S. P.; Arnett, E. M.; McPhail, A. T.; Bothner-By, A. A.; Gilkerson, W. R. "Chiral discrimination in the structures and energetics of association of stereoisomeric salts of mandelic acid with α-phenylethylamine, ephedrine, and pseudoephedrine," J. Am. Chem. Soc. 1988, 110, 1565-1580.