The gas‐phase basicities and proton affinities of amino acids and peptides

The methods of establishing gas-phase basicities and proton affinities are reviewed, particularly as applied to thermally labile and involatile molecules. The literature on the basicities of amino acids is critically reviewed, and a consistent set of gas-phase basicities for α-amino acids is recommended. The problems associated with deriving proton affinities from these data are discussed. The literature on the gas-phase basicities of peptides is reviewed, and inconsistencies in the experimental results are discussed. © 1998 John Wiley & Sons, Inc., Mass Spectrom Rev 16, 201–217, 1997

[1]  E. P. Hunter,et al.  Internal and external solvation of polyfunctional ions , 1980 .

[2]  J. W. Otvos,et al.  Cross-sections of Molecules for Ionization by Electrons , 1956 .

[3]  B. Munson,et al.  Proton affinities of some oxygenated compounds , 1973 .

[4]  C. Cassady,et al.  Gas-phase basicities of histidine and lysine and their selected di- and tripeptides , 1996, Journal of the American Society for Mass Spectrometry.

[5]  A. G. Harrison.  Chemical Ionization Mass Spectrometry , 1983 .

[6]  I. Amster,et al.  Proton affinities of the 20 common .alpha.-amino acids , 1992 .

[7]  J. Traeger,et al.  Absolute heats of formation for gas-phase cations , 1981 .

[8]  C. Fenselau,et al.  Collision energy dependence of proton-bound dimer dissociation: entropy effects, proton affinities, and intramolecular hydrogen-bonding in protonated peptides , 1993 .

[9]  B. Chait,et al.  Matrix-assisted laser desorption ionization mass-spectrometry of proteins. , 1996, Methods in enzymology.

[10]  J. Keister,et al.  The tert-butyl ion heat of formation and the isobutene proton affinity , 1993 .

[11]  J. Szulejko,et al.  Progress toward an absolute gas-phase proton affinity scale , 1993 .

[12]  M. Henchman.  Entropy-Driven Reactions: Summary of the Panel Discussion , 1987 .

[13]  I. Amster,et al.  Kinetic and thermodynamic considerations of the bracketing method: Entropy‐driven proton‐transfer reactions in a Fourier transform mass spectrometer , 1993 .

[14]  R. Cooks,et al.  Thermochemical determinations by the kinetic method , 1994 .

[15]  V. Wysocki,et al.  The effect of protonation site on bond strengths in simple peptides: Application of Ab initio and modified neglect of differential overlap bond orders and modified neglect of differential overlap energy partitioning , 1994, Journal of the American Society for Mass Spectrometry.

[16]  S. Gaskell,et al.  Sequential mass spectrometry applied to the study of the formation of , 1991 .

[17]  Effect of solvation on the acid/base properties of glycine , 1983 .

[18]  G. Bojesen.  The order of proton affinities of the 20 common L-.alpha.-amino acids , 1987 .

[19]  I. Papayannopoulos,et al.  The interpretation of collision‐induced dissociation tandem mass spectra of peptides , 1996 .

[20]  P. Thibault,et al.  Collision‐induced dissociations of peptide ions 2. Remote charge‐site fragmentations in a tandem, hybrid mass spectrometer , 1989 .

[21]  C. Fenselau,et al.  Structural Determinants of Gas Phase Basicities of Peptides , 1993 .

[22]  R. Caprioli,et al.  Fast atom bombardment mass spectrometry. , 1996, Methods in enzymology.

[23]  Joel F. Liebman,et al.  Evaluated Gas Phase Basicities and Proton Affinities of Molecules; Heats of Formation of Protonated Molecules , 1984 .

[24]  K. Walsh,et al.  Proton mobility within electrosprayed peptide ions , 1995 .

[25]  M. M. Bursey,et al.  Some proline substituent effects in the tandem mass spectrum of protonated pentaalanine. , 1992, Biological mass spectrometry.

[26]  C. Lebrilla,et al.  Intrinsic basicity of oligomeric peptides that contain glycine, alanine, and valine—The effects of the alkyl side chain on proton transfer reactions , 1995, Journal of the American Society for Mass Spectrometry.

[27]  Z. Maksić,et al.  THEORETICAL MODEL CALCULATIONS OF THE PROTON AFFINITIES OF AMINOALKANES, ANILINE, AND PYRIDINE , 1996 .

[28]  J. Fenn,et al.  Electrospray interface for liquid chromatographs and mass spectrometers. , 1985, Analytical chemistry.

[29]  P. Kebarle,et al.  Ion Thermochemistry and Solvation From Gas Phase Ion Equilibria , 1977 .

[30]  D. Lichtenberger,et al.  Correlations of lone pair ionization energies with proton affinities of amino acids and related compounds. Site specificity of protonation , 1992 .

[31]  C. Fenselau,et al.  Proton affinity of arginine measured by the kinetic approach , 1992 .

[32]  C. Cassady,et al.  Gas-phase basicities of serine and dipeptides of serine and glycine , 1994, Journal of the American Society for Mass Spectrometry.

[33]  M. Karas,et al.  Laser desorption ionization of proteins with molecular masses exceeding 10,000 daltons. , 1988, Analytical chemistry.

[34]  C. Wesdemiotis,et al.  Li+, Na+, and K+ Binding to the DNA and RNA Nucleobases. Bond Energies and Attachment Sites from the Dissociation of Metal Ion-Bound Heterodimers , 1996 .

[35]  K. Biemann.  Sequencing of peptides by tandem mass spectrometry and high-energy collision-induced dissociation. , 1990, Methods in enzymology.

[36]  C. Fenselau,et al.  A Direct Comparison of "First" and "Second" Gas Phase Basicities of the Octapeptide RPPGFSPF , 1995 .

[37]  C. Cassady,et al.  Ab Initio Studies of Neutral and Protonated Triglycines: Comparison of Calculated and Experimental Gas-Phase Basicity , 1994 .

[38]  E. Williams.  Proton transfer reactivity of large multiply charged ions. , 1996, Journal of mass spectrometry : JMS.

[39]  F. Clairet,et al.  Epimer distinction and structural effects on gas-phase acidities of alcohols measured using the kinetic method , 1992 .

[40]  C. Fenselau,et al.  Proton affinities of polyglycines assessed by using the kinetic method , 1992, Journal of the American Society for Mass Spectrometry.

[41]  D. Mueller,et al.  Hydrogen transfer reactions in the formation of “Y + 2” sequence ions from protonated peptides , 1988 .

[42]  M. Bowers,et al.  Ion-polar molecule collisions. Proton transfer reactions of butyl ions with ammonia, methylamine, diethylamine, and trimethylamine , 1973 .

[43]  S. Gronert.  An ab Initio Study of Proton Transfers from Gas-Phase Dications: Complications in Kinetic Methods for Determining Acidities , 1996 .

[44]  Torben Breindahl,et al.  On the proton affinity of some α-amino acids and the theory of the kinetic method , 1994 .

[45]  J. Szulejko,et al.  A pulsed electron beam, variable temperature, high pressure mass spectrometric re-evaluation of the proton affinity difference between 2-methylpropene and ammonia , 1991 .

[46]  R. Cooks,et al.  Gas‐phase basicities and proton affinities of lysine and histidine measured from the dissociation of proton‐bound dimers , 1994 .

[47]  A. G. Harrison,et al.  Fragmentation reactions of protonated α-amino acids , 1996 .

[48]  Banks Jf,et al.  Electrospray ionization mass spectrometry. , 1996 .

[49]  C. G. Edmonds,et al.  Electrospray ionization mass spectrometry. , 1990, Methods in enzymology.

[50]  M. Bowers,et al.  Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines , 1976 .

[51]  Brian J. Smith,et al.  Assigning absolute values to proton affinities: a differentiation between competing scales , 1993 .

[52]  K. Isa,et al.  New rules concerning the formation of protonated amino acids from protonated dipeptides using the proton affinity order determined from collisionally activated decomposition spectra , 1990 .

[53]  P. Kebarle,et al.  Gas-phase basicities of amines. Hydrogen bonding in proton-bound amine dimers and proton-induced cyclization of .alpha., .omega.-diamines , 1973 .

[54]  R. Cooks,et al.  Proton affinities from dissociations of proton-bound dimers , 1981 .

[55]  J. Salpin,et al.  A relationship between the kinetics and thermochemistry of proton transfer reactions in the gas phase , 1996 .

[56]  H. Grützmacher,et al.  Dissociation of proton-bound complexes and proton affinity of benzamides , 1994, Journal of the American Society for Mass Spectrometry.

[57]  I. Amster,et al.  Gas-phase basicity measurements of dipeptides that contain valine , 1993 .

[58]  Stéphane Bouchonnet,et al.  Proton and sodium ion affinities of glycine and its sodium salt in the gas phase. Ab initio calculations , 1992 .

[59]  F. Jensen.  Structure and stability of complexes of glycine and glycine methyl analogs with H+, Li+, and Na+ , 1992 .

[60]  J. Beauchamp,et al.  Proton Affinities of H2S and H2O , 1968 .

[61]  D. S. Gross,et al.  Experimental Measurement of Coulomb Energy and Intrinsic Dielectric Polarizability of a Multiply Protonated Peptide Ion Using Electrospray Ionization Fourier-Transform Mass Spectrometry , 1995 .

[62]  A. G. Harrison,et al.  A kinetic approach to the proton affinities of amine bases , 1993 .

[63]  J. Gal,et al.  Superbases in the gas phase: Amidine and guanidine derivatives with proton affinities larger than 1000 kj mol−1 , 1993 .

[64]  M. Bowers,et al.  Chapter 9 – Stabilities of positive ions from equilibrium gas-phase basicity measurements , 1979 .

[65]  A. G. Harrison,et al.  Chemical ionization of amino acids. , 1976, Journal of the American Chemical Society.

[66]  E. P. Hunter,et al.  Ion thermochemistry of low-volatility compounds in the gas phase. 1. Intrinsic basicities of .alpha.-amino acids , 1979 .

[67]  R. Georgiadis,et al.  Empirical methods for determination of ionization gauge relative sensitivities for different gases , 1983 .

[68]  C. Cassady,et al.  Determination of the gas-phase basicities of proline and its di- and tripeptides with glycine: the enhanced basicity of prolylproline. , 1996, Journal of mass spectrometry : JMS.

[69]  D. Bohme,et al.  Flowing afterglow studies at york university , 1975 .

[70]  M. T. Bowers,et al.  New design of an ion cyclotron resonance cell capable of temperature variation over the range 80< or =T< or =450 K. , 1978, The Review of scientific instruments.

[71]  H. Schaefer,et al.  Proton affinities of lysine and histidine : a theoretical consideration of the discrepancy between experimental results from the kinetic and bracketing methods , 1993 .

[72]  Alice Chung-Phillips,et al.  Experimental and Ab Initio Studies on Protonations of Alanine and Small Peptides of Alanine and Glycine , 1995 .

[73]  R. Taft,et al.  A theoretical and experimental study of the intrinsic basicities of methyldiazoles , 1990 .

[74]  C. Cassady,et al.  Experimental and ab initio studies of the gas-phase basicities of polyglycines , 1993 .

[75]  M. Haas,et al.  The fragmentation of proton-bound cluster ions and the gas-phase acidities of alcohols , 1993 .

[76]  Stephen A. Martin,et al.  Mass spectrometric determination of the amino acid sequence of peptides and proteins , 1987 .

[77]  R. L. Hunter,et al.  EXPERIMENTAL DETERMINATION OF THE ACIDITY AND BASICITY OF GLYCINE IN THE GAS PHASE , 1979 .

[78]  C. Fenselau,et al.  Assessment of Gas Phase Basicities of Protonated Peptides by the Kinetic Method , 1995 .

[79]  A. G. Harrison,et al.  Proton mobility in protonated amino acids and peptides , 1997 .

[80]  A. McCormack,et al.  Fragmentation of protonated peptides: surface-induced dissociation in conjunction with a quantum mechanical approach. , 1993, Analytical chemistry.

[81]  Vicki H. Wysocki,et al.  Influence of Peptide Composition, Gas-Phase Basicity, and Chemical Modification on Fragmentation Efficiency: Evidence for the Mobile Proton Model , 1996 .

[82]  C. Lebrilla,et al.  Gas-phase basicities and sites of protonation of glycine oligomers (GLYn; n = 1-5) , 1993 .