A Study of Formation and Fragmentation of Ionic Complexes of α-Amino Acids and Peptides with Al(III)-Glycerol by Fast Atom Bombardment Mass Spectrometry

Saraswathi, Mandapati; Miller, Jack M.

doi:10.1002/(sici)1097-0231(199610)10:13<1706::aid-rcm723>3.0.co;2-p

Cited by 7 publications

(8 citation statements)

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“…This is consistent with the dissociation of [M + 117] + ions derived from α-amino acids, peptides and glycols. 11, 12 Our study demonstrates that metal chelation with modified dinucleotide analogues may be useful both to probe biologically relevant interactions and to mimic the mechanism by which far larger systems operate.…”

Section: Discussionmentioning

confidence: 89%

Complexation of transition-metal ions, SnII, PbII and Al III with nucleobase-substituted polyethers and dissociation of adduct ions studied by fast atom bombardment mass spectrometry

Saraswathi¹,

Miller²

1997

J. Chem. Soc., Dalton Trans.

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Section: Discussionmentioning

confidence: 89%

Complexation of transition-metal ions, SnII, PbII and Al III with nucleobase-substituted polyethers and dissociation of adduct ions studied by fast atom bombardment mass spectrometry

Saraswathi¹,

Miller²

1997

J. Chem. Soc., Dalton Trans.

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“…40 In an investigation of the CID of Al 3+ complexes composed of amino acids and glycerol (generated by FAB), the major fragmentation route that was observed for the phenylalanine complex involved the loss of H 2 O and CO along with neutral species from the glycerol ligand. 39 It has also been observed that the fragmentation of Ni + , Cu + , and Co + complexes with aliphatic amino acids also proceeded via the net loss of 46 Th. 81 The current consensus is that the elimination of H 2 O and CO from amino acids occurs via the rapid, consecutive loss of the two species.…”

Section: Resultsmentioning

confidence: 99%

“…The interactions between molecules bearing electron-donating groups such as amines, [1][2][3][4][5][6][7][8][9] carbonyls and alcohols, [10][11][12][13][14][15][16] crown ethers, [17][18][19][20][21][22][23][24][25][26] glymes, 22,27,28 cryptands, [29][30][31] and calixarenes [32][33][34][35] and alkali or transition metal ions have been investigated using a variety of mass spectrometric techniques. In addition, the collision-induced dissociation (CID) of metal-ion adducts of biomolecules such as amino acids, [36][37][38][39][40][41][42][43][44][45][46][47][48] peptides,…”

Section: Introductionmentioning

confidence: 99%

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Elucidation of Fragmentation Pathways for the Collision-Induced Dissociation of the Binary Ag(I) Complex with Phenylalanine

et al. 2001

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During our ongoing investigation of the formation and reactivity of gas-phase complex ions composed of Ag(I) and various R-amino acids, we discovered that the mass-to-charge ratio for the major collision-induced dissociation (CID) product generated from a binary Ag + complex with phenylalanine was consistent with the formation of an Ag + complex with an aldehyde. In this study we investigated and compared the fragmentation pathways for complexes of Ag + with phenylalanine, phenylalanine with exchangeable protium replaced with deuterium, phenylalanine with the carboxylic acid group labeled with 13 C, and phenylalanine with the benzylic group labeled with deuterium. The reaction pathways were determined using multidimensional dissociation steps in an ion-trap mass spectrometer. The dissociation experiments provide clear evidence for the formation of several novel product species, including the Ag + complex with phenylacetaldehyde, as well as the formation of an Ag + complex with either a benzyl carbene or styrene. These dissociation products are markedly different from those observed following the fragmentation of other transition and alkali metal adducts of phenylalanine. On the basis of the dissociation of the various isotope-exchanged and -labeled versions of phenylalanine, we propose several reaction pathways that implicate the formation of an Ag + complex with an aziridinone (Rlactam), for which a peak at the correct mass-to-charge ratio was observed in the MS/MS spectrum of the (M + Ag) + ion. A comparison of the apparent reactivity toward water and methanol in the ion-trap mass spectrometer of the Ag + -containing product ions to Ag + complexes with various low-mass organic molecules provided further evidence to support the proposed formation of the aldehyde and styrene complexes with Ag + ions. For instance, the apparent reactivity of the Ag + /aldehyde product ion generated from the CID of the (M + Ag) + ion is identical to that observed for a complex produced by the electrospray ionization of a solution containing Ag + ions and neat phenylacetaldehyde. Similar results were obtained for a dissociation product ion assumed to be a complex composed of Ag + ions and styrene.

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“…In the case of, for example, peptides1–12 and oligosaccharides,13–15 investigating such interactions in the gas phase allows one to probe metal ion affinity and binding sites in the absence of solvent. The interactions between metal ions and amino acids have also been investigated,16–28 with interests including such factors as metal ion affinity, dissociation reaction pathways and chiral resolution.…”

Section: Introductionmentioning

confidence: 99%

Influence of a ring substituent on the tendency to form H₂O adducts to Ag⁺ complexes with phenylalanine analogues in an ion trap mass spectrometer

et al. 2002

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In a previous report we showed that certain binary Ag(+)-amino acid complexes formed adduct ions by the attachment of a single water and methanol molecule when stored in an ion trap mass spectrometer: complexes with aliphatic amino acids and with 4-fluorophenylalanine formed the adduct ions whereas complexes with phenylalanine and tryptophan did not. In this study we compared the tendency of the Ag(+) complexes derived from phenylalanine, 4-fluorophenylalanine, 4-hydroxyphenylalanine (tyrosine), 4-bromophenylalanine, 4-nitrophenylalanine and aminocyclohexanepropionic acid to form water adducts when stored, without further activation, in the ion trap for times ranging from 1 to 500 ms. Because the donation of pi electron density to the Ag(+) ion is a likely determining factor in complex reactivity, our aim in the present study was to determine qualitatively the influence of para-position substituents on the aromatic ring on the formation of the water adducts. Our results show that the reactivity of the complexes is influenced significantly by the presence of the various substituents. Decreases in [M + Ag](+) ion abundance, and increases in adduct ion abundance, both measured as a function of storage time, follow the trend -NO(2) > -Br > -F > -OH > -H. The complex of Ag(+) with 4-nitrophenylalanine was nearly as reactive towards water as the Ag(+) complex with aminocyclohexanepropionic acid, the last being an amino acid devoid of pi character in the ring system. Collision induced dissociation of the [M + Ag](+) species derived from the amino acids produces, among other products, Ag(+) complexes with a para-substituted phenylacetaldehyde: complexes that also form adduct species when stored in the ion trap. The trends in adduct ion formation exhibited by the aldehyde-Ag(+) complex ions were similar to those observed for the precursor complexes of Ag(+) and the amino acids, confirming the influence of the ring substituent.

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A Study of Formation and Fragmentation of Ionic Complexes of α-Amino Acids and Peptides with Al(III)-Glycerol by Fast Atom Bombardment Mass Spectrometry

Abstract: The site of the metal-ion interaction is mostly at the amide nitrogens.

Cited by 7 publications

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Complexation of transition-metal ions, SnII, PbII and Al III with nucleobase-substituted polyethers and dissociation of adduct ions studied by fast atom bombardment mass spectrometry

Complexation of transition-metal ions, SnII, PbII and Al III with nucleobase-substituted polyethers and dissociation of adduct ions studied by fast atom bombardment mass spectrometry

Elucidation of Fragmentation Pathways for the Collision-Induced Dissociation of the Binary Ag(I) Complex with Phenylalanine

Influence of a ring substituent on the tendency to form H₂O adducts to Ag⁺ complexes with phenylalanine analogues in an ion trap mass spectrometer

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A Study of Formation and Fragmentation of Ionic Complexes of α-Amino Acids and Peptides with Al(III)-Glycerol by Fast Atom Bombardment Mass Spectrometry

Abstract: The site of the metal-ion interaction is mostly at the amide nitrogens.

Cited by 7 publications

References 0 publications

Complexation of transition-metal ions, SnII, PbII and Al III with nucleobase-substituted polyethers and dissociation of adduct ions studied by fast atom bombardment mass spectrometry

Complexation of transition-metal ions, SnII, PbII and Al III with nucleobase-substituted polyethers and dissociation of adduct ions studied by fast atom bombardment mass spectrometry

Elucidation of Fragmentation Pathways for the Collision-Induced Dissociation of the Binary Ag(I) Complex with Phenylalanine

Influence of a ring substituent on the tendency to form H2O adducts to Ag+ complexes with phenylalanine analogues in an ion trap mass spectrometer

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Influence of a ring substituent on the tendency to form H₂O adducts to Ag⁺ complexes with phenylalanine analogues in an ion trap mass spectrometer