Analysis of native amino acid and peptide enantiomers by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry

Journal of Mass Spectrometry

Volumn 39, Issue 2, 2004, Pages 177-187

  Desai, Meera J ^a   Armstrong, Daniel W ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Atmospheric pressure chemical ionization; Chiral; Liquid chromatography mass spectrometry; Native amino acids; Peptides; Teicoplanin

Indexed keywords

AMINO ACIDS; AMMONIUM COMPOUNDS; ATMOSPHERIC PRESSURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONIZATION; POLYPEPTIDES;

ELECTROSPRAY IONIZATION (ESI); FLOW RATES;

MASS SPECTROMETRY;

ALANINE; AMINO ACID; AMMONIUM DERIVATIVE; ARGININE; ASPARAGINE; ASPARTIC ACID; CARNITINE; CYSTEINE; FORMIC ACID; GLUTAMIC ACID; GLUTAMINE; HISTIDINE; ISOLEUCINE; LEUCINE; LYSINE; METHANOL; NORLEUCINE; NORVALINE; ORNITHINE; PEPTIDE; PHENYLALANINE; PROLINE; PYROGLUTAMIC ACID; SERINE; THREONINE; TRYPTOPHAN; TYROSINE; VALINE; WATER;

AMINO ACID ANALYSIS; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOMER; ENANTIOSELECTIVITY; FLOW RATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTERMETHOD COMPARISON; ION PAIR CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR WEIGHT; PEPTIDE ANALYSIS; PRIORITY JOURNAL; SENSITIVITY ANALYSIS; SEPARATION TECHNIQUE; ULTRAVIOLET RADIATION;

AMINO ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; PEPTIDES; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM;

EID: 1442325502     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.571     Document Type: Article

References (44)

1. Food and Drug Administration. FDA's policy statement for the development of new stereoisomeric drugs. Chirality 1992; 4: 338.
2. Peter A, Vekes E, Gera L, Stewart JM, Armstrong DW. A comparison of the direct and indirect LC methods for separating enantiomers of unusual glycine and alanine amino acid analogues. Chromatographia (Suppl.) 2002; 56: S79.
3. Husek P, Simek P. Advances in amino acid analysis. LC-GC 2001; 19: 986.
4. Dash AK, Sawhney A. A simple LC method with UV detection for the analysis of creatine and creatinine and its application to several creatine formulations. J. Pharm. Biomed. Anal. 2002; 29: 939.
5. Jegorov A, Triska J, Trnka T, Cerny M. Separation of alpha-amino acid enantiomers by reversed-phase high-performance liquid chromatography after derivatization with o-phthaldialdehyde and a sodium salt of 1-thio-beta-D-glucose. J. Chromatogr. 1988; 434: 417.
6. Schuster R. Determination of amino acids in biological, pharmaceutical, plant and food samples by automated precolumn derivatization and high-performance liquid chromatography. J. Chromatogr. 1988; 431: 271.
7. Stocchi V, Piccoli G, Magnani M, Palma F, Biagiarelli B, Cucchiarini L. Reversed phase high-performance liquid chromatography separation of dimethylaminoazobenzene sulfonyl- and dimethylaminoazobenzene thiohydantoin- amino acid derivatives for amino acid analysis and microsequencing studies at the picomole level. Anal. Biochem. 1989; 178: 107.
8. Praminik BC, Moomaw CR, Evans CT, Cohen SA, Slaughter CA. Identification of phenylthiocarbamyl amino acids for compositional analysis by thermospray liquid chromatography/mass spectrometry. Anal. Biochem. 1989; 176: 269.
9. Sherwood RA, Titheradge AC, Richards DA. Measurement of plasma and urine amino acids by high-performance liquid chromatography with electrochemical detection using phenylisothiocynate derivatization. J. Chromatogr. 1990; 528: 293.
10. Pronce T, Tilquin B. Trace analysis in chiral separation of selected amino enantiomers. J. Pharm. Biomed. Anal. 1996; 14: 1175.
11. Tcherkas YV, Denisenko AD. Simultaneous determination of several amino acids, including homocysteine, cysteine and glutamic acid, in human plasma by isocratic reversed-phase high-performance liquid chromatography with fluorimetric detection. J. Chromatogr. A 2001; 913: 309.
12. Hemmermeister DE, Serrano J, Schmeider P, Kuehl D. Characterization of dansylated glutathione, glutathiondisulfide, cysteine and cystine by narrow bore liquid chromatography/electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2000; 14: 503.
13. Yao Z-P, Wan TSM, 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. 2000; 72: 5383.
14. Yao Z-P, Wan TSM, Kwong K-P, Che C-T. Chiral analysis by electrospray ionization mass spectrometry/mass spectrometry. 2. Determination of enantiomeric excess of amino acids. Anal. Chem. 2000; 72: 5394.
15. Grigorean G, Ramirez J, Ahn SE, Lebrilla CB. A mass spectrometry method for the determination of enantiomeric excess in mixtures of D,L-amino acids. Anal. Chem. 2000; 72: 4275.
16. Augusti DV, Carazza F, Augusti R, Tao WA, Cooks RG. Quantitative chiral analysis of sugars by electrospray ionization tandem mass spectrometry using modified amino acids as chiral reference compounds. Anal. Chem. 2002; 74: 3458.
17. Galaverna G, Corradini R, Dallavalle F, Folesani G, Dossena A, Marchelli R. Chiral separation of amino acids by copper(II) complexes of tetradentate diaminodiamido-type ligands added to the eluent in reversed-phase high-performance liquid chromatography: a ligand exchange mechanism. J. Chromatogr. A 2001; 922: 151.
18. Wu L, Tao WA, Cooks RG. Kinetic method for the simultaneous chiral analysis of different amino acids in mixtures. J. Mass Spectrom. 2003; 38: 386.
19. Armstrong DW. The evolution of chiral stationary phases for liquid chromatography. LC-GC. 1997; May: S20.
20. Armstrong DW, Zhang B. Chiral Stationary Phases for HPLC. Anal. Chem. 2001; 73: 557A.
21. Berthod A, Liu Y, Bagwill C, Armstrong DW. Facile liquid chromatographic enantioresolution of native amino acids and peptides using a teicoplanin chiral stationary phase. J. Chromatogr. A 1996; 731: 123.
22. Peter A, Torok G, Armstrong DW. High-performance liquid chromatographic separation of enantiomers of unusual amino acids on a teicoplanin chiral stationary phase. J. Chromatogr. A 1998; 793: 283.
23. Berthod A, Chen X, Kullman JP, Armstrong DW, Gasparrini F, D'Acquarica I, Villani C, Carotti A. Role of the carbohydrate moieties in chiral recognition on teicoplanin-based LC stationary phases. Anal. Chem. 2000; 72: 1767.
24. Berthod A, Valleix A, Tizon V, Leonce E, Caussignac C, Armstrong DW. Retention and selectivity of teicoplanin stationary phases after copper complexation and isotopic exchange. Anal. Chem. 2001; 73: 5499.
25. Yu Y-P, Wu S-H. Simultaneous analysis of enantiomeric composition of amino acids and N-acetyl-amino acids by enantioselective chromatography. Chirality 2001; 13: 231.
26. Petritis K, Valleix A, Elfakir C, Dreux M. Simultaneous analysis of underivatized chiral amino acids by liquid chromatography-ionspray tandem mass spectrometry using a teicoplanin chiral stationary phase. J. Chromatogr. A 2001; 913: 331.
27. Chaimbault P, Petritis K, Elfakir C, Dreux M. Determination of 20 underivatized proteinic amino acids by ion-pairing chromatography and pneumatically assisted electrospray mass spectrometry. J. Chromatogr. A 1999; 855: 191.
28. Casetta B, Tagliacozzi D, Shshan B, Federici G. Development of a method for rapid quantitation of amino acids by liquid chromatography - tandem mass spectrometry (LC-MSMS) in plasma. Clin. Chem. Lab. Med. 2000; 38: 391.
29. Petritis J, Chaimbault P, Elfakir C, Dreux M. Parameter optimization for the analysis if underivatized protein amino acids by liquid chromatography and ionspray tandem mass spectrometry. J. Chromatogr. A 2001; 896: 253.
30. Qu J, Chen W, Luo G, Wang Y, Xiao S, Ling Z, Chen G. Rapid determination of underivatized pyroglutamic acid, glutamic acid, glutamine, and other relevant amino acids in fermentation media by LC-MS-MS. Analyst 2002; 127: 66.
31. Anacardio R, Cantalini MG, Angelis FD, Gentile M. Quantification of S-carboxyrnethyl-(R)-cysteine in human plasma by high-performance ion-exchange liquid chromatography/atmospheric pressure ionization mass spectrometry. J. Mass Spectrom. 1997; 32: 388.
32. Vishwanathan K, Tackett RL, Stewart JT, Bartlett MG. Determination of arginine and methylated arginines in human plasma by liquid chromatography-tandem mass spectrometry. J. Chromatogra. B 2000; 748: 157.
33. Yokoyama Y, Ozaki O, Sato H. Separation and determination of amino acids, creatine, bioactive amines and nucleic acid bases by dual-mode gradient ion-pair chromatography. J. Chromatogr. A 1996; 739: 333.
34. Jin D, Nagakura K, Murofushi S, Miyahara T, Toyo'oka T. Total resolution of 17 DL-amino acids labeled with a fluorescent chiral reagent, R(-)-4-(3-isothiocyanatopyrrolodin-1-yl)-7-(N,N-dimethylaminosulfonyl) -2,1,3-benzoxadiazole, by high-performance liquid chromatography. J. Chromatogr. A 1998; 822: 215.
35. Yu H, Ding YS, Mou SF, Jandik P, Cheng J. Simultaneous determination of amino acids and carbohydrates by anion-exchange chromatography with integrated pulsed amperometric detection. J. Chromatogr. A 2002; 966: 89.
36. Ermer J, Vogel M. Application of hyphenated LC-MS techniques in pharmaceutical analysis. Biomed. Chromatogr. 2000; 14: 373.
37. Amad MH. Cech NB, Jackson GS, Enke CG. Importance of gas-phase proton affinities in determining the electrospray ionization response for analytes and solvents. J. Mass Spectrom. 2000; 35: 784.
38. Harrison AG. The gas-phase basicities and proton affinities of amino acids and peptides. Mass Spectrom. Rev. 1997; 16: 201.
39. Thurman EM, Ferrer I, Barcelo D. Choosing between atmospheric pressure chemical ionization and electrospray ionization interfaces for the HPLC/MS analysis of pesticides. Anal. Chem. 2001; 73: 5441.
40. Abian J. The coupling of gas and liquid chromatography with mass spectrometry. J. Mass Spectrom. 1999; 34: 157.
41. Voyksner RD. In Electrospray Ionization Mass Spectrometry, Cole RB (ed). Wiley: New York 1997; 325.
42. Ekins R, Edwards P. On the meaning of 'sensitivity.' Clin. Chem. 1997; 43: 1824.
43. Choi BK, Hercules DM, Gusey AI. Effect of liquid chromatography separation of complex matrices on liquid chromatography-tandem mass spectrometry signal suppression. J. Chromatogr. A 2001; 907: 337.
44. Choi BK, Hercules DM, Gusey AI. LC-MS/MS signal suppression effects in the analysis of pesticides in complex environmental matrices. Fresenius' J. Anal. Chem. 2001; 369: 370.