Mass Spectrometric Determination of the Amino-Acid Sequence of Peptides

Shemyakin, M. M.; Ovchinnikov, Yu.A.; Kiryushkin, A. A.; Vinogradova, E. I.; Мирошников, А. И.; Alakhov, Yu.B.; Липкин, В. М.; Shvetsov, Yu. B.; Wulfson, N.S.; Rosinov, B.V.; Bochkarev, V. N.; Burikov, V. M.

doi:10.1038/211361a0

Cited by 31 publications

(11 citation statements)

References 7 publications

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“…It should be pointed out that 9,lO-dihydrophenantrene-type structures of the molecule ions a of 1-16 shown in Schemes 1-3 are conjectural, but consistent with previously published literature data.l6sI7 The principal mass fragmentation pathways of N-substituted amino acids (3,6,9,12,15,17,19) are similar to those of their metameric methyl esters (1, 4, 7, 10, 13, 16, 18) and hydrazides (2, 5, 8,11,14) but show differences in the abundances of the important ions.…”

Section: Rwults and Discussionsupporting

confidence: 85%

“…N-substituted a-alanine (3) and P-phenyl-P-alanine (6, 9, 17, 19) may be distinguished from metameric methyl esters (1 and 4, 7, 16, 18 The methyl esters of N-substituted P-phenyl-P-alanines (4, 7) may be distinguished from their metameric Of P I . N-Substituted tryptophans (12, 15) may be distinguished from their metameric methyl esters (10, 13) and hydrazides (11,14) on the basis of the lowest values of p3. The hydrazides of N-substituted tryptophan (11,14) may be distinguished from their metameric Nsubstituted amino acids and methyl esters (10, 12, 13, 15) on the basis of the highest values of p,, p2 and p3.…”

Section: (Iii) In the Series Of Metameric N-substituted Fl-mentioning

confidence: 99%

“…N-Substituted tryptophans (12, 15) may be distinguished from their metameric methyl esters (10, 13) and hydrazides (11,14) on the basis of the lowest values of p3. The hydrazides of N-substituted tryptophan (11,14) may be distinguished from their metameric Nsubstituted amino acids and methyl esters (10, 12, 13, 15) on the basis of the highest values of p,, p2 and p3.…”

Section: (Iii) In the Series Of Metameric N-substituted Fl-mentioning

confidence: 99%

“…The values of p,-pr calculated from the EI mass spectra recorded at 75 eV (15 eV)P of N-(E)stilbenyloxyalkylcarbonyl-substituted a-alanine (3) and fbphenyl-Palanines (6, 9) and their metameric methyl esters (1, 4, 7) and hydrazides (2, 5, 8) and of N-(E)-stilbenyloxyalkylcarbonylsubstituted tryptophan (12, 15) and their metameric methyl esters (10, 13) and hydrazides(11,14) and of N-(E)-stilbenyloxyalkylcarbonyl-substituted /I-phenyl-/I-alanines(17,19) and their metameric methyl esters(16,18) …”

mentioning

confidence: 99%

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Mass spectrometry of N‐substituted amino acids and their derivatives: Correlation of the abundances of the M^+. and selected fragment ions of metamers

Wyrzykiewicz

Prukała

1994

Org. Mass Spectrom.

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The mass spectral fragmentations of nineteen new metameric N-(E)-stilbenyloxyalkylcarboayl-[or (E)4'chlorostilbenyloxyalkylcarbonyl)~ -substituted amino acids and their metameric methyl esters and hydrazides were investigated. Fragmentation pathways are proposed on the basis of accurate mass and metastable transition measurements. The correlation between the intensities of M+' and the selected fragment ions of these compounds is discussed. The data obtained create the basis for distinguishing metamers.

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Section: Rwults and Discussionsupporting

confidence: 85%

Section: (Iii) In the Series Of Metameric N-substituted Fl-mentioning

confidence: 99%

Section: (Iii) In the Series Of Metameric N-substituted Fl-mentioning

confidence: 99%

mentioning

confidence: 99%

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Mass spectrometry of N‐substituted amino acids and their derivatives: Correlation of the abundances of the M^+. and selected fragment ions of metamers

Wyrzykiewicz

Prukała

1994

Org. Mass Spectrom.

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“…M ass spectrometry has found increasing use as a tool for analyzing the sequence of amino acids in peptides (Biemann et al, 1966;Shemyakin et a/., 1966;Thomas et a/., 1968). Apart from a few instances where it has been applied to peptides isolated from proteins (Geddes et NI., 1969) the method has been used principally upon synthetic peptides of known structure or on peptide antibiotics.…”

mentioning

confidence: 97%

Application of Mass Spectrometry to Protein Chemistry. I. Method for Amino-Terminal Sequence Analysis of Proteins.

Gray¹,

Valle²

1970

Biochemistry

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Fragmentation behaviour ofN-acylamino-O-alkyl ester derivatives of an aliphatic tripeptide in negative ion mass spectrometry

Lauber

Schlunegger

1988

Biol. Mass Spectrom.

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The N-acetyl-, N-trifluoroacetyl-, N-pentafluoropropioayl-and N-heptafluorobutylamino derivatives of the tripeptide valyl-alanyl-leucine have been synthesized in every combination with the carboxy derivatives O-methyl ester, O-(l-H,H)-trifluoroethyI ester, 041-H,H)-pentafluoropropyl ester and 041-H,H)-heptafluorobutyl ester. These 16 derivatives have been mass measured after negative ionization using a 10% CO,/Ar moderator gas mixture in an electron impact ion source of a VGZAB2F mass spectrometer. The fragmentation behaviour of the peptide derivatives have been studied by negative linked-scan, negative mass-analysed ion kinetic energy and charge inversion mass spectrometry. Mast detected sequence ions originate from N-terminal fragments. Recorded anion currents and linked-scan measurement have shown that fluoro residues at the C-terminus increase the intensities of sequence ions, whereas N-terminal perfhoroalkyl derivatives generate [M -HFI-and [M -2HFl-ions. The abundances of these fragment ions increase with increasing molecular weight of the N-terminal residues. The best sequence information with intense anion currents has been recorded with the peptide derivative Ntrifluoroacetylarnino-0-hepatafluorobutyl ester.

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Mass Spectrometric Determination of the Amino-Acid Sequence of Peptides

Cited by 31 publications

References 7 publications

Mass spectrometry of N‐substituted amino acids and their derivatives: Correlation of the abundances of the M^+. and selected fragment ions of metamers

Mass spectrometry of N‐substituted amino acids and their derivatives: Correlation of the abundances of the M^+. and selected fragment ions of metamers

Application of Mass Spectrometry to Protein Chemistry. I. Method for Amino-Terminal Sequence Analysis of Proteins.

Fragmentation behaviour ofN-acylamino-O-alkyl ester derivatives of an aliphatic tripeptide in negative ion mass spectrometry

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Mass Spectrometric Determination of the Amino-Acid Sequence of Peptides

Cited by 31 publications

References 7 publications

Mass spectrometry of N‐substituted amino acids and their derivatives: Correlation of the abundances of the M+. and selected fragment ions of metamers

Mass spectrometry of N‐substituted amino acids and their derivatives: Correlation of the abundances of the M+. and selected fragment ions of metamers

Application of Mass Spectrometry to Protein Chemistry. I. Method for Amino-Terminal Sequence Analysis of Proteins.

Fragmentation behaviour ofN-acylamino-O-alkyl ester derivatives of an aliphatic tripeptide in negative ion mass spectrometry

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Mass spectrometry of N‐substituted amino acids and their derivatives: Correlation of the abundances of the M^+. and selected fragment ions of metamers

Mass spectrometry of N‐substituted amino acids and their derivatives: Correlation of the abundances of the M^+. and selected fragment ions of metamers