Abstract
Developments in the analysis of amino acids and peptides by gas chromatography—mass spectrometry (GC/MS) have occurred in a chemical rather than a microbiological context. The presentation in this chapter, therefore, describes advances in technique and structural determination and is leavened, where possible, with examples drawn from the application of GC/MS to microbial metabolism and biochemistry. This chapter does not purport to be an exhaustive review of the relevant literature. Citations have been omitted not from an inherent lack of merit or relevance but because they are accessible through later citations of the same authors or through the more specialized reviews cited.
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References
Abramson, F. P., McCaman, M. W., and McCaman, R. E., 1974, Femtomole level of analysis of biogenic amines and amino acids using functional group mass spectrometry, Anal. Biochem. 57:482.
Adams, R. F., 1974, Determination of amino acid profiles in biological samples by gas chromatography, J. Chromatogr. 95:189.
Adams, R. F., Vandemark, F. L., and Schmidt, G. J., 1977, Ultramicro GC determination of amino acids using glass open tubular columns and a nitrogen-selective detector, J. Chromatogr. Sci. 15:63.
Anderegg, R. J., Biemann, K., Manmade, A., and Ghosh, A. C., 1979, Mass spectrometric peptide sequencing: Cyclochlorotine, Biomed. Mass Spectrom. 6:129.
Andersson, C.-O., 1958, Mass spectrometric studies on amino acid and peptide derivatives, Acta Chem. Scand. 12:1353.
Aragozzini, F., Ferrari, A., Pacini, N., and Gualandris, R., 1979, Indole-3-lactic acid as a tryptophan metabolite produced by Bifidobacterîum spp., Appl. Environ. Microbiol. 38:544.
Batley, K. E., and Morris, H. R., 1977, Dihydrofolate reductase: Partial sequence of the Lactobacillus casei enzyme and homology with other dihydrofolate reductases, Biochem. Soc. Trans. 5:1097.
Bengtsson, G., and Odham, G., 1979, A micromethod for the analysis of free amino acids by gas chromatography and its application to biological systems, Anal. Biochem. 92:426.
Bengtsson, G., Odham, G., and Westerdahl, G., 1981, Glass capillary gas Chromatographie analysis of free amino acids in biological microenvironments using electron capture or selected ion-monitoring detection, Anal. Biochem. 111:163.
Benninghoven, A., and Sichtermann, W. K., 1978, Detection, identification and structural investigation of biologically important compounds by secondary ion mass spectrometry, Anal. Chem. 50:1180.
Beuhler, R. J., Flanigan, E., Greene, L. J., and Friedman, L., 1974a, Proton transfer mass spectrometry of underivatized peptides, Biochemistry 13:5060.
Beuhler, R. J., Flanigan, E., Greene, L. J., and Friedman, L., 1974b, Proton transfer mass spectrometry of peptides. A rapid heating technique for underivatized peptides containing arginine, J. Am. Chem. Soc. 96:3990.
Biemann, K., Gapp, F., and Seibl, J., 1959, Application of mass spectrometry to structure problems. I. Amino acid sequence in peptides, J. Am. Chem. Soc. 81:2274.
Blau, K., and King, G., 1978, Handbook of Derivatives for Chromatography ,Heyden and Son, Ltd., London.
Budzikiewicz, H., and Meissner, G., 1978, Chemical ionization spectra of trimethylsilylated amino acids and oligopeptides, Org. Mass. Spectrom. 13:608.
Calas, B., Mery, J., Parello, J., Prome, J. C., Roussel, J., and Patouraux, D., 1980, Field desorption mass spectrometry of basic peptides. An approach to the sequencing of arginine-containing peptides, Biomed. Mass Spectrom. 7:288.
Cancalon, P., and Klingman, J. D., 1974, An improved procedure for preparing the n-butyltrifluoroacetyl amino acid derivatives and its application in the study of radioactive amino acids from biological sources, J. Chromatogr. Sci. 12:349.
Caprioli, R. M., and Seifert, W. E., 1975, Hydrolysis of polypeptides and proteins utilizing a mixture of dipeptidylaminopeptidases with analysis by GC/MS, Biochem. Biophys. Res. Commun. 64:295.
Cattabeni, F., Galli, C. L., and Eros, T., 1976, A simple and highly sensitive mass fragmentographic procedure for gamma amino butyric acid determinations, Anal. Biochem. 72:1.
Cotter, R. J., 1980, Mass spectrometry of nonvolatile compounds; Desorption from extended probes, Anal. Chem. 52:1589A.
Coulter, A. W., and Fenselau, C. C., 1972, Variation of fragmentation with ring size in cyclic a-amino acids, Org. Mass Spectrom. 6:105.
Das, B. C., Gero, S. D., and Lederer, E., 1967, lV-Methylation of N-acyl oligopeptides, Biochem. Biophys. Res. Commun. 29:211.
Dell, A., and Morris, H. R., 1974, New observations on the fragmentation properties of peptides under electron impact mass spectrometry, Biochem. Biophys. Res. Commun. 61:1125.
Dell, A., and Morris, H. R., 1977, A mass spectrometric strategy for the rapid screening of homologous proteins: Studies on a Pseudomonas azurin, Biochem. Biophys. Res. Com- mun. 78:874.
Dell, A., Williams, D. H., Morris, H. R., Smith, G. A., Feeney, J., and Roberts, G. C. K., 1975, Structure revision of the antibiotic echinomycin, J. Am. Chem. Soc. 97:2497.
DeJongh, D. C., Faus, F., Nayar, M. S. B., Boileau, G., and Brakier-Gingras, L., 1976. The use of lV-succinyl derivatives in the study of amino acids and peptides by mass spectrometry, Biomed. Mass Spectrom. 3:191.
Desgres, J., Boisson, D., and Padieu, P., 1979, Gas-Liquid chromatography of isobutyl ester, N(O)-heptafluorobutyrate derivatives of amino acids on a glass capillary column for quantitative separation in clinical biology, J. Chromatogr. 162:133.
Dillard, J. G., 1973, Negative ion mass spectrometry, Chem. Rev. 73:589.
Engelfried, C., Koenig, W. A., and Voelter, W., 1976, Mass spectrometric investigation of peptide amides, Biomed. Mass Spectrom. 3:241.
Fairwell, T., Barnes, W. T., Richards, F. F., and Lovins, R. E., 1970, Sequence analysis of complex protein mixtures by isotope dilution and mass spectrometry, Biochemistry 9:2260.
Fairwell, T., Ellis, S., and Lovins, R. E., 1973, Quantitative protein sequencing using mass spectrometry: Thermally induced formation of thiohydantoin amino acid derivatives from iV-methyl and JV-phenylthiourea amino acids and peptides in the mass spectrometer, Anal. Biochem. 53:115.
Fales, H. M., Nagai, Y., Milne, G. W. A., Brewer, H. B., Jr., Bronzert, T. J., and Pisano, J. J., 1971, Use of chemical ionization mass spectrometry in analysis of amino acid phenylthiohydantoin derivatives formed during Edman degradation of proteins, Anal. Biochem. 43:288.
Fales, H. M., Milne, G. W. A., Winkler, H. U., Beckey, H. D., Damico, J. N., and Barron, R., 1975, Comparison of mass spectra of some biologically important compounds as obtained by various ionization techniques, Anal. Chem. 47:207.
Felker, P., and Bandurski, R. S., 1975, Quantitative gas-liquid chromatography and mass spectrometry of the N(O)-perfluorobutyryl-O-isoamyl derivatives of amino acids, Anal. Biochem. 67:245.
Frank, H., and Desiderio, D. M., 1978, Reduction of oligopeptides to amino alcohols with borane, Anal. Biochem. 90:413.
Frank, H., Haegele, K. D., and Desiderio, D. M., 1977, Gas chromatography-mass spectrometry study of acetylacetonyl dipeptide methyl esters, Anal. Chem. 49:287.
Frank, H., das Neves, H. J. C., and Bayer, E., 1978, Use of borane as reducing agent in sequence analysis of peptides by gas chromatography-mass spectrometry, J. Chromatogr. 152:357.
Frick, W., Chang, D., Folkers, K., and Daves, G. D., Jr., 1977a, Critical experimental parameters in gas chromatographic-mass spectrometric analysis of oligopeptide hydrolysates at the picomole level, Anal. Chem. 49:1241.
Frick, W., Daves, G. D., Jr., Barofsky, D. F., Barofsky, E., Fisher, G. H., Chang, D., and Folkers, K., 1977b, Sample derivatization and structure analysis by field desorption mass spectrometry. Peptide methylation-methanolysis, Biomed. Mass Spectrom. 4:152.
Fujita, T., Takaishi, Y., and Shiromoto, T., 1979, New peptide antibiotic, Hypelcin A, from Hypocrea peltata, J. Chem. Soc, Chem. Commun. 413.
Gaffney, J. S., Pierce, R. C., and Friedman, L., 1977, Mass spectrometer study of evaporation of a-amino acids, J. Am. Chem. Soc. 99:4293.
Gelpi, E., Koenig, W. A., Gibert, J., and Oro, J., 1969, Combined gas chromatography-mass spectrometry of amino acid derivatives, J. Chromatogr. 7:604.
Gerber, G. E., Anderegg, R. J., Herlihy, W. C., Gray, C. P., Biemann, K., and Khorana, H. G., 1979, Partial primary structure of bacteriorhodopsin: Sequencing methods for membrane proteins, Proc. Nat. Acad. Sci. USA 76:227.
Gray, W. R., Wojcik, L. H., and Futrell, J. H., 1970, Application of mass spectrometry to protein chemistry II. Chemical ionization studies on acetylated permethylated peptides, Biochem. Biophys. Res. Commun. 41:1111.
Grob, K., Grob, G., and Grob, K., Jr., 1979, Deactivation of glass capillary columns by silylation. Part I: Principles and basic technique, HRCCCJ. High Resolut. Chromatogr. Chromatogr. Commun. 1:31.
Hansen, G., and Munson, B., 1978, Surface chemical ionization mass spectrometry, Anal. Chem. 50:1130.
Hirota, A., Suzuki, A., Aizawa, K., and Tamura, S., 1974, Mass spectrometric determination of amino acid sequence in Cyl-2, a novel cyclotetrapeptide from Cylindrocladium scoparium, Biomed. Mass Spectrom. 1:15.
Hunt, D. F., Stafford, G. C., Jr., Crow, F. W., and Russell, J. W., 1976, Pulsed positive negative ion chemical ionization mass spectrometry, Anal. Chem. 48:2098.
Hunt, D. F., Ðuko, A. M., Ballard, J., and Shabanowitz, J., 1979, Polypeptide sequencing by mass spectrometry: New methodology, Proc. 27th Annual Conference on Mass Spectrometry and Allied Topics ,Seattle, Washington, p. 608.
Husek, P., 1974, Derivation of amino acids with 1,3-dichlorotetrafluoroacetone and its use in gas chromatography, J. Chromatogr. 91:475.
Husek, P., and Macek, K., 1975, Gas chromatography of amino acids, J. Chromatogr. 113:139.
Iwase, H., and Murai, A., 1977, On the derivatives for the ultramicro determination of amino acids by mass fragmentography, Anal. Biochem. 78:340.
Jayasimhulu, K., and Day, R. A., 1980a, Electron impact fragmentation of oxazoles and oxazinones derived from leucine and isoleucine, Biomed. Mass Spectrom. 7:7.
Jayasimhulu, K., and Day, R. A., 1980b, Mass spectrometric determination of TV terminal tryptophan and N- terminal histidine in peptides, Biomed. Mass Spectrom. 7:321.
Jennings, W., 1980, Evolution and application of the fused silica column HRCCC., J. High Resolut. Chromatogr. Chromatogr. Commun. 3:601.
Jönsson, J., Eyem, J., and Sjöquist, J., 1973, Quantitative gas Chromatographic analysis of amino acids on a short glass capillary column, Anal. Biochem. 51:204.
Kaiser, F. E., Gehrke, C. W., Zumwalt, R. W., and Kuo, K. C., 1974, Amino acid analysis. Hydrolysis, ion-exchange clean-up, derivatization, and quantitation by gas liquid chromatography, J. Chromatogr. 94:113.
Kamal, F., Katz, E., and Mauger, A. B., 1978, Electrophoretic, Chromatographie and mass spectrometric procedures for the identification and isotopic assay of amino acid constituents in etamycin, J. Chromatogr. 151:245.
Kamiya, Y., Sakurai, A., Tamura, S., Takahashi, N., Abe, K., Tsuchiya, E., Fukui, S., Kitada, C., and Fujino, M., 1978, Structure of rhodotorucine A, a novel lipopeptide, inducing mating tube formation in Rhodosporidium toruloides, Biochem. Biophys. Res. Commun. 83:1077.
Katz, E., Mason, K. T., and Mauger, A. B., 1974, The presence of -amino-ß,-dihydroxybutyric acid in hydrolysates of actinomycin Z1, J. Antiobiot. XXVII:952.
Katz, E., Mason, K. T., and Mauger, A. B., 1975, 3-Hydroxy-5-methylproline, a new amino acid identified as a component of actinomycin Z1, Biochem. Biophys. Res. Commun. 63:502.
Kingston, E. E., and Duffield, A. M., 1978, Plasma amino acid quantitation using gas chromatography chemical ionization mass spectrometry and 13C amino acids as internal standards, Biomed. Mass Spectrom. 5:621.
Knapp, D. R., 1979, Handbook of Analytical Derivatization Reactions ,Wiley-Interscience, New York.
Kondrat, R. W., and Cooks, R. G., 1978, Direct analysis of mixtures by mass spectrometry, Anal. Chem. 50:81A.
Krutzsch, H. C., and Kindt, T. J., 1979, The identification of trimethylsilylated dipeptides with chemical ionization mass spectrometry, Anal. Biochem. 92:525.
Krutzsch, H. C., and Pisano, J. J., 1977, “Analysis of Dipeptides by Gas ChromatographyMass Spectrometry and Application to Sequencing with Dipeptidyl Aminopeptidases,” Methods in Enzymology ,(C. W. Hirs and S. N. Timasheff, eds.), Vol XLVII, pp. 391–404, Academic Press, New York.
Krutzsch, H. C., and Pisano, J. J., 1978, Separation and sequence of dipeptides using gas chromatography and mass spectrometry of their trimethylsilylated derivatives, Biochemistry 17:2791.
Lawless, J. G., and Chadha, M. C., 1971, Mass spectrometric analysis of C3 and C4 aliphatic amino acid derivatives, Anal. Biochem. 44:473.
Leclercq, P. A., and Desiderio, D. M., 1973, Chemical ionization mass spectra of amino acids and derivatives. Occurrence and fragmentation of ion-molecule reaction products, Org. Mass. Spectrom. 7:515.
Leimer, K. R., Rice, R. H., and Gehrke, C. W., 1977a, Complete mass spectra of lV-trifluoroacetyl-rt-butyl esters of amino acids, J. Chromatogr. 141:121.
Leimer, K. R., Rice, R. H., and Gehrke, C. W., 1977b, Complete mass spectra of the per-trimethylsilylated amino acids, J. Chromatogr. 141:355.
Liardon, R., Ott-Kuhn, U., and Husek, P., 1979, Mass spectra of -amino acid oxazolidinones, Biomed. Mass Spectrom. 6:381.
Liardon, R., Ledermann, S., and Ott, U., 1981, Determination of D-amino acids by deuterium labelling and selected ion monitoring, J. Chromatogr. 203:385.
Lindley, H., and Davis, P. C., Gas chromatography of some dipeptide derivatives, J. Chromatogr. 100:117.
Loder, P. B., and Abraham, E. P., 1971, Isolation and nature of intra cellular peptides from a Cephalosporin C-producing Cephalosporium sp., Biochem. J. 123:471.
Macfarlane, R. D., and Torgerson, D. F., 1976, Californium-252 plasma desorption mass spectrometry, Science 191:920.
MacKenzie, S. L., 1981, “Recent Developments in Amino Acid Analysis by Gas-Liquid Chromatography,” in Methods of Biochemical Analysis (D. Glick, ed.), Vol. 27, pp. 1–88, Wiley-Interscience, New York.
MacKenzie, S. L., and Hogge, L. R., 1977, Gas chromatography-mass spectrometry of the lV(O)-heptafluorobutyryl isobutyl esters of the protein amino acids using electron impact ionization, J. Chromatogr. 132:485.
MacKenzie, S. L., and Tenaschuk, D., 1974, Gas liquid chromatography of N-heptafluorobutyryl isobutyl esters of amino acids, J. Chromatogr. 97:19.
MacKenzie, S. L., and Tenaschuk, D., 1979a, Quantitative formation of N(O,S)- heptafluorobutyryl isobutyl amino acids for gas Chromatographic analysis. I. Esterification, J. Chromatogr. 171:195.
MacKenzie, S. L. ,and Tenaschuk, D., 1979b, Quantitative formation of N(O,S)- heptafluorobutyryl isobutyl amino acids for gas Chromatographic analysis. II. Acylation, J. Chromatogr. 173:53.
Mahajan, V. K., and Desiderio, D. M., 1978, Mass spectrometry of acetylated, permethylated and reduced oligopeptides, Biochem. Biophys. Res. Commun. 82:1104.
Manhas, M. S., Hsieh, R. S., and Bose, A. K., 1970, Mass spectral studies. Part VII. Unusual fragmentation of some N-trifìuoroacetyl amino-acid methyl esters, J. Chem. Soc, C. 116.
March, J. F., 1975, Modified technique for the quantitative analysis of amino acids by gas chromatography using heptafluorobutyric rc-propyl derivatives, Anal. Biochem. 69:420.
Marik, J. ,Capek, A., and Kralicek, J., 1976, Gas chromatography-mass spectrometry of trimethylsilyl derivatives of -amino acids, J. Chromatogr. 128:1.
Martinez, E., and Gelpi, E., 1978, Mixed pentafluoropropionyl trimethylsilyl derivatives of 5-hydroxytryptophan for mass fragmentographic detection. Development of a retention index model for substituted indoles, J. Chromatrogr. 167:77.
Maugh, T., 1980, Separations by MS speed up, simplify analysis, Science 209:675.
McReynolds, J. H., and Anbar, M., 1977, Isotopic assay of nanomole amounts of nitrogen-15 labeled amino acids by collision-induced dissociation mass spectrometry, Anal. Chem. 49:1832.
Mee, J. M. L., Korth, J., Halpern, B., and James, L. B., 1977, Rapid and quantitative blood amino acid analysis by chemical ionization mass spectrometry, Biomed. Mass Spectrom. 4:178.
Meot-Ner, M., and Field, F. H., 1973, Chemical ionization mass spectrometry. XX. Energy effects and virtual ion temperature in the decomposition kinetics of amino acids and amino acid derivatives, J. Am. Chem. Soc. 95:7207.
Meuzelaar, H. L. C., Posthumus, M. A., Kistemaker, P. G., and Kistemaker, J., 1973, Curie point pyrolysis in direct combination with low voltage electron impact ionization mass spectrometry. New method for the analysis of nonvolatile organic materials, Anal. Chem. 45:1546.
Morris, H. R., 1972, Studies towards the complete sequence determination of proteins by mass spectrometry; a rapid procedure for the successful permethylation of histidine containing peptides, FEBS (Fed. Eur. Biochem. Soc.) Lett. 22:257.
Morris, H. R., 1980, Biomolecular structure determination by mass spectrometry, Nature 286:447.
Morris, H. R., and Dell, A., 1975, The sequence of the blocked N-terminal peptide from Neurospora glutamate dehydrogenase, Biochem. J. 149:754.
Morris, H. R., Williams, D. H., and Ambler, R. P., 1971, Determination of the sequences of protein-derived peptides and peptide mixtures by mass spectrometry, Biochem. J. 125:189.
Morris, H. R., Dickinson, R. J., and Williams, D. H., 1973, Studies towards the complete sequence determination of proteins by mass spectrometry: Derivatization of methionine, cysteine and arginine containing peptides, Biochem. Biophys. Res. Commun. 51:247.
Morris, H. R., Batley, K. E. ,Harding, N. G. L. ,Bjur, R. A., Dann, J. G., and King, R. W., 1974, Dihydrofolate reductase: Low-resolution mass-spectrometric analysis of an elastase digest as a sequencing tool, Biochem. J. 137:409.
Moss, C. W., Lambert, M. A., and Diaz, F. J., 1971, GLC of twenty protein amino acids on a single column, J. Chromatogr. 60:134.
Mudgett, M., Bowen, D. V., Kindt, T. J., and Field, F. H., 1975, C-Methylation: An Artifact in peptides derivatized for sequencing by mass spectrometry, Biomed. Mass Spectrom. 2:254.
Mudgett, M., Bowen, D. V., Field, F. H., and Kindt, T. J., 1977, Peptide sequencing: The utility of chemical ionization mass spectrometry, Biomed. Mass Spectrom. 4:159.
Mudgett, M., Sogn, J. A., Bowen, D. V., and Field, F. H., 1978, Peptide sequencing by chemical ionization mass spectrometry, Adv. Mass Spectrom. 7B:1506.
Nakagawa, Y., Nakazawa, T., and Shoji, J., 1975, On the structure of a new antibiotic TL-119 (Studies on antibiotics from the genus Bacillus. VI), J. Antibiot. 28:1004.
Nau, H., 1974, New dideutero-perfluoroalkylated oligopeptide derivatives for proteinsequencing by gas chromatography-mass spectrometry, Biochem. Biophys. Res. Comm. 59:1088.
Nau, H., 1976, Gas chromatography-mass spectrometry of permethylated peptides and their reduced and trimethylsilylated derivatives, J. Chromatogr. 121:376.
Nau, H., 1978, Sequencing of polypeptides containing asparagine and glutamine residues by gas chromatography-mass spectrometry, Adv. Mass Spectrom. 7B:I5I8.
Nau, H., and Biemann, K., 1976a, Amino acid sequencing by gas chromatography-mass spectrometry using perfluoro-dideuteroalkylated peptide derivatives. A. Gas Chromatographie retention indices, Anal. Biochem. 73:139.
Nau, H., and Biemann, K., 1976b, Amino acid sequencing by gas chromatography-mass spectrometry using perfluoro-dideuteroalkylated peptide derivatives. B. Interpretation of the mass spectra, Anal. Biochem. 73:154.
Okada, K., and Sakuno, A., 1978, Identification of amino acid thiohydantoin derivatives by chemical ionization mass spectrometry, Org. Mass Spectrom. 13:535.
Okada, K., Nagai, S. ,Uyehara, T., and Hiramoto, M., 1974, A study of some new and useful lV-terminal groups in mass spectrometry of peptides. The use of 3-hydroxyalkanoyl and unsaturated acyl groups, Tetrahedron 30:1175.
Padieu, P., Desgres, J., and Maume, B. F., 1978a, Chemical ionization in capillary column gas chromatography-quadropole mass spectrometry: An ideal combination for structure proof and fragmentation mechanism elucidation as well as for isotopic dilution mass fragmentography, Finnigan Spectra 7:No. 1.
Padieu, P., Desgres, J., Maume, B. F., Van der Velde, G., and Skinner ,R. S., 1978b, Investigation of the chemical ionization of amino acid derivatives for biological studies, Adv. Mass Spectrom. 7B:1604.
Pandey, R. C., Meng, H., Cook, J. C., Jr., and Rinehart, K. L., Jr., 1977, Structure of antiamoebin I from high resolution field desorption and gas Chromatographic mass spectrometry studies, J. Am. Chem. Soc. 99:5203.
Patil, G. V., Hamilton ,R. E., and Day, R. A., 1973, Schiff base derivatives of peptide esters: Relative abundance of N-terminal, C-terminal and “internal” fragments as a function of the blocking group, Org. Mass Spectrom. 7:817.
Pearce, R. J., 1977, Amino acid analysis by gas-liquid chromatography of N- heptafluorobutyryl isobutyl esters. Complete resolution using a support-coated opentubular capillary column, J. Chromatogr. 136:113.
Pereira, W. E., Hoyano, Y., Reynolds, W. E., Summons, R. E., and Duffield, A. M., 1973, Simultaneous quantitation of ten amino acids in soil extracts by mass fragmentography, Anal. Biochem. 55:236.
Poole, C. F., and Verzele, M., 1978, Separation of protein amino acids as their iV(O)-acyl alkyl ester derivatives on glass capillary columns, J. Chromatogr. 150:439.
Priddle, J. D., 1974, The use of mass-spectrometry to complement conventional techniques for protein sequence determination, Biochem. J. 139:23.
Priddle, J. D., Rose, K., and Offord, R. E., 1976a, The separation and sequencing of permethylated peptides by mass spectrometry directly coupled to gas-liquid chromatography, Biochem. J. 157:777.
Priddle, J. D., Rose, K., and Offord, R. E., 1976b, Direct sequencing of permethylated peptides by gas chromatography-mass spectrometry using electron impact and chemical ionization, Adv. Mass Spectrom. Biochem. Med. II:477.
Priddle, J. D., Rose, K., and Offord, R. E., 1978, Amino acid sequence determination by direct e.i./c.i. mass spectrometry of N-acyl: N,O-permethylated oligopeptides separated by gas chromatography, Adv. Mass Spectrom. 7B:1502.
Rafter, J. J., Ingelman-Sundberg, M., and Gustafsson, J.-A., 1979, Protein amino acid analysis by an isotope ratio gas chromatography mass spectrometry computer technique, Biomed. Mass Spectrom. 6:317.
Rangarajan, M., Ardrey, R. E., and Darbre, A., 1973, Gas-liquid chromatography and mass spectrometry of amino acid thiohydantoins and their use in protein sequencing, J. Chromatogr. 87:499.
Rash, J. J., Gehrke, C. W., Zumwalt, R. W., Kuo, K. C., Kvenvolden, K. A., and Stalling, D. L., 1972, GLC of amino acids: A survey of contamination, J. Chromatogr. Sci. 10:444.
Robinson, J. R., Starratt, A. N., and Schlahetka, E. E., 1978, Estimation of nitrogen-15 levels in derivatized amino acids using gas chromatography-quadropole mass spectrometry with chemical ionization and selected ion monitoring, Biomed. Mass Spectrom. 5:648.
Schier, G. M., Halpern, B., and Milne, G. W. A., 1974, Characterization of dipeptides by electron impact and chemical ionization mass spectrometry, Biomed. Mass Spectrom. 1:212.
Schier, G. M., Bolton, P. D., and Halpern, B., 1976, The mass spectrometric identification of dipeptide mixtures obtained from dipeptidylaminopeptidase I-Hydrolysates, Biomed. Mass Spectrom. 3:32.
Schulman, M. F., and Abramson, F. P., 1975, Plasma amino acid analysis by isotope ratio gas chromatography-mass spectrometry computer techniques, Biomed. Mass Spectrom. 2:9.
Schulten, H.-R., 1977, “Field Desorption Mass Spectrometry and its Application in Biochemical Analysis,” in Methods of Biochemical Analysis (D. Glick, ed.), Vol. 24, pp. 313– 448, Wiley-Interscience, New York.
Schulten, H.-R., and Wittmann-Liebold, B., 1976, High resolution field desorption mass spectrometry V. Mixtures of amino acid phenylthiohydantoins and Edman degradation products, Anal. Biochem. 76:300.
Segura, J., Artigas, F., Martinez, E., and Gelpi, E., 1976, Adsorption of tryptophan metabolites from physiological fluids on XAD-2 and determination by single ion monitoring, Biomed. Mass Spectrom. 3:91.
Seifert, W. E., Jr., McKee, R. E., Beckner, C. F., and Caprioli, R. M., 1978, Characterization of mixtures of dipeptides by gas chromatography-mass spectrometry, Anal. Biochem. 88:149.
Shaw, W. V., Packman, L. C., Burleigh, B. D., Dell, A., Morris, H. R., and Hartley, B. S., 1979, Primary structure of a chloramphenicol acetyltransferase specified by R plasmids, Nature 282:870.
Shieh, J.-J., Leung, K., and Desiderio, D. M., 1976, Basic mass spectrometric investigations of amino acid-fluorescamine derivatives, Org. Mass Spectrom. 11:479.
Siezen, R. J., and Mague, T. H., 1977, Gas-liquid chromatography of the N- heptafluorobutyryl isobutyl esters of fifty biologically interesting amino acids, J. Chromatogr. 130:151.
Sjöquist, B., 1979, Analysis of tyrosine and deuterium labelled tyrosine in tissues and body fluids, Biomed. Mass Spectrom. 6:392.
Stapleton, B. J., and Bowie, J. H., 1976, Electron impact studies. CIII-Negative ion mass spectra of naturally occurring compounds: Nitrobenzoyl derivatives of amino esters, Org. Mass Spectrom. 11:429.
Stimpson, B. P., and Evans, C. A., Jr., 1978, Electrohydrodynamic ionization mass spectrometry of biochemical materials, Biomed. Mass Spectrom. 5:52.
Summons, R. E., Pereira, W. E., Reynolds, W. E., Rindfleisch, T. C., and Duffield, A. M., 1974, Analysis of twelve amino acids in biological fluids by mass fragmentography, Anal. Chem. 46:582.
Sun, T., and Lovins, R. E., 1972, Quantitative protein sequencing using mass spectrometry: Use of low ionizing voltages in mass spectral analysis of methyland phenylthiohydantoin amino acid derivatives, Anal. Biochem. 45:176.
Suzuki, T., Song, K.-D., Itagaki, Y., and Tuzimura, K., 1976, Mass spectrometric identication of amino acid thiohydantoins, Org. Mass Spectrom. 11:557.
Tobe, H., Morishima, H., Naganawa, H., Takita, T., Aoyagi, T., and Umezawa, H., 1979, Structure and chemical synthesis of amastatin, Agr. Biol. Chem. 43:591.
Tsang, C. W., and Harrison, A. G., 1976, Chemical ionization of amino acids, J. Am. Chem. Soc. 98:1301.
Ueno, T., Nakashima, T., Uemoto, M., Fukami, H., Lee, S.-N., and Izumiya, N., 1977, Mass spectrometry of Altemaria mali toxins and related cyclodepsipeptides, Biomed. Mass Spectrom. 4:134.
Voigt, D., and Schmidt, J., 1978, Negative ion mass spectrometry of natural products. VIII-a-amino acids, Biomed. Mass Spectrom. 5:44.
Waern, R., and Falter, H., 1978, An approach to the differentiation of leucine and isoleucine residues in EI mass spectra of peptides, Biochem. Biophys. Res. Commun. 81:448.
Weber, R., and Levsen, K., 1980, Collision induced dissociation of field desorbed diand tripeptides, Biomed. Mass Spectrom. 7:314.
Wegmann, H., Curtius, H.-Ch., and Redweik, U., 1978, Selective ion monitoring of tryptophan, N- acetyltryptophan and kynurenine in human serum. Application to the in vivo measurement of tryptophan pyrrolase activity, J. Chromatogr. 158:305.
Weinkam, R. J., 1978, Reactions of protonated diamino acids in the gas phase, J. Org. Chem. 43:2581.
Wiecek, C., Halpern, B., Sargeson, A. M., 1979, The determination of steric purity of amines and amino acids by gas chromatography and mass spectrometry, Org. Mass Spectrom. 14:281.
Wietzerbin, J., Das, C. D., Petit, J.-F., Lederer, E., Leyh-Bouille, M, and Ghuysen, J.M., 1974, Occurrence of D-alanyl-(D)-raesø-diaminopimelic acid and mesø-diaminopimelylmeso- diaminopimelic acid linkages in the peptidoglycan of Mycobacteria, Biochemistry 13:3471.
Winkler, H. U., and Beckey, H. D., 1972, Field desorption mass spectrometry of amino acids, Org. Mass Spectrom. 6:655.
Wipf, H. K., Irving, P., McCamish, M., Venkataraghavan, R., and McLafferty, F. W., 1973, Mass spectrometric studies of peptides. V. Determination of amino acid sequences in peptide mixtures by mass spectrometry, J. Am. Chem. Soc. 95:3369.
Wolfensberger, M, Redwik, U., and Curtius, H.-Ch., 1979, Gas chromatography mass spectrometry and selected ion monitoring of the N,N-dipentafluoropropionyl hexafluoroisopropyl ester of glutamine, J. Chromatogr. 172:471.
Zanetta, Z. P., and Vincendon, G., 1973, GLC of the N(O)-heptafluorobutyryl isoamyl esters of amino acids. 1. Separation and quantitative determination of the constituent amino acids of proteins, J. Chromatogr. 76:91.
Ziemer, J. N., Perone, S. P., Caprioli, R. M., and Seifert, W. E., 1979, Computerized pattern recognition applied to gas chromatrography-mass spectrometry identification of pentafluoropropionyl dipeptide methyl esters, Anal. Chem. 51:1732.
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© 1984 Plenum Press, New York
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MacKenzie, S.L. (1984). Amino Acids and Peptides. In: Odham, G., Larsson, L., Mårdh, PA. (eds) Gas Chromatography Mass Spectrometry Applications in Microbiology. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-4526-8_6
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