Diastereochemical Differentiation of Some Cyclic and Bicyclic β-Amino Acids, Via the Kinetic Method

Journal of the American Society for Mass Spectrometry

Volumn 20, Issue 1, 2009, Pages 34-41

  Hyyryläinen, Anna R M ^a   Pakarinen, Jaana M H ^a   Fülöp, Ferenc ^b   Vainiotalo, Pirjo ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b UNIVERSITY OF SZEGED   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINO ACIDS; COPPER; DENSITY FUNCTIONAL THEORY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METAL IONS; OLEFINS; ORGANIC ACIDS;

AB INITIO; CYCLOHEXENE; DIASTEREOMERIC; DIASTEREOMERS; HYBRID DENSITY FUNCTIONAL THEORIES; KINETIC METHODS; NORBORNANE; NORBORNENE; REFERENCE COMPOUNDS; RIGID STRUCTURES; STEREOCHEMICAL DIFFERENTIATIONS; TRIMERIC COMPLEXES;

AMINES;

2 AMINOCYCLOHEXANE 2 AMINO 4 CYCLOHEXENE; 2 AMINOCYCLOPENTANECARBOXYLIC ACID; AMINO ACID DERIVATIVE; BETA AMINO ACID; COPPER; CYCLOPENTANE BETA AMINO ACID; NICKEL; NORBORNANE BETA AMINO ACID; NORBORNANE DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; KINETICS; MASS SPECTROMETRY; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ALGORITHMS; AMINO ACIDS, CYCLIC; COPPER; CYCLOHEXANECARBOXYLIC ACIDS; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NICKEL; NORBORNANES; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

EID: 57649176845     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2008.09.018     Document Type: Article

References (30)

1. McLuckey S.A., Cameron D., and Cooks R.G. Proton Affinities from Dissociations of Proton-Bound Dimers. J. Am. Chem. Soc 103 (1981) 1313-1317
2. McLuckey S.A., Patrick J.S., Kotiaho T., and Cooks R.G. Thermochemical Determinations by the Kinetic Method. Mass Spectrom. Rev 13 (1994) 287-339
3. Koskinen J.T., Thomas P.D., and Cooks R.G. The Kinetic Method of Making Thermochemical Determinations. J. Mass Spectrom 34 (1999) 85-92
4. Vékey K., and Czira G. Distinction of Amino Acid Enantiomers Based on the Basicity of Their Dimers. Anal. Chem 69 (1997) 1700-1705
5. Shen W., Wong P.S.H., and Cooks R.G. Stereoisomeric Distinction by the Kinetic Method: 2,3-Butanediol. Rapid Commun. Mass Spectrom 11 (1997) 71-74
6. Tao W.A., Zhang D., Wang F., Thomas P.D., and Cooks R.G. Kinetic Resolution of D,L-Amino Acids Based on Gas-Phase Dissociation of Copper(II) Complexes. Anal. Chem 71 (1999) 4427-4429
7. Tao W.A., Zhang D., Nikolaev E.N., and Cooks R.G. Copper(II)-Assisted Enantiomeric Analysis of D,L-Amino Acids Using the Kinetic Method: Chiral Recognition and Quantification in the Gas Phase. J. Am. Chem. Soc 122 (2000) 10598-10609
8. Zhang D., Tao W.A., and Cooks R.G. Chiral Resolution of D- and L-Amino Acids by Tandem Mass Spectrometry of Ni(II)-Bound Trimeric Complexes. Int. J. Mass Spectrom 204 (2001) 159-169
9. Wu L., Tao W.A., and Cooks R.G. Ligand and Metal-Ion Effects in Metal-Ion Clusters Used for Chiral Analysis of α-Hydroxy Acids by the Kinetic Method. Anal. Bioanal. Chem 373 (2002) 618-627
10. Wu L., and Cooks R.G. Chiral Analysis Using the Kinetic Method with Optimized Fixed Ligands: Applications to Some Antibiotics. Anal. Chem 75 (2003) 678-684
11. Tao W.A., Clark R.L., and Cooks R.G. Quotient Ratio Method for Quantitative Enantiomeric Determination by Mass Spectrometry. Anal. Chem 74 (2002) 3783-3789
12. Tao W.A., Gozzo F.C., and Cooks R.G. Mass Spectrometric Quantification of Chiral Drugs by the Kinetic Method. Anal. Chem 73 (2001) 1692-1698
13. Augusti D.V., Carazza F., Augusti R., Tao W.A., and Cooks R.G. Quantitative Chiral Analysis of Sugars by Electrospray Ionization Tandem Mass Spectrometry Using Modified Amino Acids as Chiral Reference Compounds. Anal. Chem 74 (2002) 3458-3462
14. Young B.L., and Cooks R.G. Improvements in Quantitative Chiral Determinations Using the Mass Spectrometric Kinetic Method. Int. J. Mass Spectrom 267 (2007) 199-204
15. Tao W.A., Wu L., and Cooks R.G. Differentiation and Quantitation of Isomeric Dipeptides by Low-Energy Dissociation of Copper(II)-Bound Complexes. J. Am. Soc. Mass Spectrom 12 (2001) 490-496
16. Schug K.A., Lemr K., and Lindner W. Isomeric Discrimination of Arginine-Containing Dipeptides Using Electrospray Ionization-Ion Trap Mass Spectrometry and the Kinetic Method. J. Am. Soc. Mass Spectrom 15 (2004) 840-847
17. Schug K.A., and Lindner W. Stereoselective Discrimination and Quantification of Arginine and N-Blocked Arginine Enantiomers by Formation and Dissociation of Calcium-Mediated Diastereomeric Trimer Complexes with a Chiral Reference Compound Using Electrospray Ionization-Ion Trap Tandem Mass Spectrometry. J. Am. Soc. Mass Spectrom 16 (2005) 825-834
18. Wu L., Meurer E.C., Young B., Yang P., Eberlin M.N., and Cooks R.G. Isomeric Differentiation and Quantification of α,β-Amino Acid-Containing Tripeptides by the Kinetic Method: Alkali Metal-Bound Dimeric Cluster Ions. Int. J. Mass Spectrom 231 (2004) 103-111
19. Nagaveni V., Prabhakar S., and Vairamani M. Differentiation of Underivatized Diastereomeric Hexosamine Monosaccharides and Their Quantification in a Mixture Using the Kinetic Method under Electrospray Ionization Conditions. Anal. Chem 76 (2004) 3505-3509
20. Wu L., Meurer E.C., and Cooks R.G. Chiral Morphing and Enantiomeric Quantification in Mixtures by Mass Spectrometry. Anal. Chem 76 (2004) 663-671
21. Fülöp F. The Chemistry of 2-Aminocycloalkanecarboxylic Acids. Chem. Rev 101 (2001) 2181-2204
22. Martinek T.A., Tóth G.K., and Fülöp F. Application of Alicyclic β-Amino Acids in Peptide Chemistry. Chem. Soc. Rev 35 (2006) 323-334
23. Partanen T., Stájer G., Bernáth G., Göndös G., Pihlaja K., and Vainiotalo P. Mass Spectral Fragmentation Reactions of Some Stereoisomeric Cyclic β-Amino Acids under Electron and Chemical Ionization. Rapid Commun. Mass Spectrom 7 (1993) 1121-1125
24. Hyyryläinen A.R.M., Pakarinen J.M.H., Stájer G., Fülöp F., and Vainiotalo P. Diastereochemical Differentiation of β-Amino Acids Using Host-Guest Complexes Studied by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. J. Am. Soc. Mass Spectrom 18 (2007) 1038-1045
25. Hyyryläinen A.R.M., Pakarinen J.M.H., Fülöp F., and Vainiotalo P. Differentiation of Diastereomeric Cyclic β-Amino Acids by Varying the Neutral Reagent in Ion/Molecule Reactions Studied by Electrospray Ionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. Rapid Commun. Mass Spectrom 22 (2008) 1-8
26. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Rev. C. 02 (2004), Gaussian, Inc, Wallingford CT
27. Seymour J.L., Malkov A.V., Kočovský P., and Tureček F. Chiral Recognition in Solution and the Gas Phase. Experimental and Theoretical Studies of Aromatic D- and L-Amino Acid-Cu(II)-Chiragen Complexes. J. Mass Spectrom 39 (2004) 1044-1052
28. GaussView 3.0, Gaussian, Inc., CT, USA.
29. Tureček F. Copper-Biomolecule Complexes in the Gas Phase. The Ternary Way. Mass Spectrom. Rev 26 (2007) 563-582
30. Alvarez E.J., Vartanian V.H., and Brodbelt J.S. Metal Complexation Reactions of Quinolone Antibiotics in a Quadrupole Ion Trap. Anal. Chem 69 (1997) 1147-1155