Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition
Abstract The elimination of carbon monoxide and water from a series of protonated dipeptides, [XxxYyy + H]+, is investigated by tandem mass spectrometry experiments and density functional theory. The combined results show that CO loss occurs on the $ a_{1} $-$ y_{1} $ pathway, which begins by rearra...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Pingitore, Francesco [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2004 |
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| Schlagwörter: |
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| Anmerkung: |
© American Society for Mass Spectrometry 2004 |
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| Übergeordnetes Werk: |
Enthalten in: Journal of the American Society for Mass Spectrometry - Washington, DC : ACS Publications, 1990, 15(2004), 7 vom: 01. Juli, Seite 1025-1038 |
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| Übergeordnetes Werk: |
volume:15 ; year:2004 ; number:7 ; day:01 ; month:07 ; pages:1025-1038 |
| Links: |
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| DOI / URN: |
10.1016/j.jasms.2004.03.014 |
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| Katalog-ID: |
SPR031488765 |
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| 003 | DE-627 | ||
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| 008 | 201007s2004 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1016/j.jasms.2004.03.014 |2 doi | |
| 035 | |a (DE-627)SPR031488765 | ||
| 035 | |a (SPR)j.jasms.2004.03.014-e | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Pingitore, Francesco |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition |
| 264 | 1 | |c 2004 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a © American Society for Mass Spectrometry 2004 | ||
| 520 | |a Abstract The elimination of carbon monoxide and water from a series of protonated dipeptides, [XxxYyy + H]+, is investigated by tandem mass spectrometry experiments and density functional theory. The combined results show that CO loss occurs on the $ a_{1} $-$ y_{1} $ pathway, which begins by rearrangement of the added proton to the amide N-atom and creates the proton-bound dimer of an amino acid (Yyy) and an imine (that from Xxx residue). The loss of $ H_{2} $O is initiated from a tautomer in which the added proton has migrated to the hydroxyl group of the C-terminus, thereby promoting the formation of an ion with protonated oxazolone structure (a nominal $ b_{2} $ ion). The highest yields of [XxxYyy+H−CO]+ and [XxxYyy+H−$ H_{2} $O]+ are observed at threshold energies. As the internal energy of the protonated dipeptides increases, these primary products are depleted by consecutive dissociations yielding mostly backbone fragments. Specifically, [XxxYyy+H−CO]+ decomposes to $ y_{1} $ (protonated Yyy) and $ a_{1} $ (immonium ion of Xxx residue), while [XxxYyy+H−$ H_{2} $O]+ produces $ a_{2} $ and the immonium ions of residues Xxx ($ a_{1} $) and Yyy (“internal” immonium ion). Water loss takes place more efficiently when the more basic residue is at the C-terminal position. Increasing the basicity of the N-terminal residue enhances the extent of CO versus $ H_{2} $O loss and introduces the competitive elimination of $ NH_{3} $. The dissociations leading to eliminations of small neutrals (CO, $ H_{2} $O, etc.) generally proceed over transition states that lie higher in energy than the corresponding dissociation products. The excess energy is disposed of either in translational or rovibrational modes of the products, depending on the stability of the incipient noncovalent assemblies emerging during the cleavage of the small neutrals. | ||
| 650 | 4 | |a Collisionally Activate Dissociation |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Oxazolone |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a GlyGly |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a AlaAla |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Protonated Peptide |7 (dpeaa)DE-He213 | |
| 700 | 1 | |a Polce, Michael J. |4 aut | |
| 700 | 1 | |a Wang, Ping |4 aut | |
| 700 | 1 | |a Wesdemiotis, Chrys |4 aut | |
| 700 | 1 | |a Paizs, Béla |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Journal of the American Society for Mass Spectrometry |d Washington, DC : ACS Publications, 1990 |g 15(2004), 7 vom: 01. Juli, Seite 1025-1038 |w (DE-627)320598799 |w (DE-600)2019911-9 |x 1879-1123 |7 nnns |
| 773 | 1 | 8 | |g volume:15 |g year:2004 |g number:7 |g day:01 |g month:07 |g pages:1025-1038 |
| 856 | 4 | 0 | |u https://dx.doi.org/10.1016/j.jasms.2004.03.014 |z lizenzpflichtig |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a SYSFLAG_A | ||
| 912 | |a GBV_SPRINGER | ||
| 912 | |a GBV_ILN_20 | ||
| 912 | |a GBV_ILN_22 | ||
| 912 | |a GBV_ILN_23 | ||
| 912 | |a GBV_ILN_24 | ||
| 912 | |a GBV_ILN_31 | ||
| 912 | |a GBV_ILN_32 | ||
| 912 | |a GBV_ILN_39 | ||
| 912 | |a GBV_ILN_40 | ||
| 912 | |a GBV_ILN_60 | ||
| 912 | |a GBV_ILN_62 | ||
| 912 | |a GBV_ILN_63 | ||
| 912 | |a GBV_ILN_65 | ||
| 912 | |a GBV_ILN_69 | ||
| 912 | |a GBV_ILN_70 | ||
| 912 | |a GBV_ILN_73 | ||
| 912 | |a GBV_ILN_74 | ||
| 912 | |a GBV_ILN_95 | ||
| 912 | |a GBV_ILN_100 | ||
| 912 | |a GBV_ILN_101 | ||
| 912 | |a GBV_ILN_105 | ||
| 912 | |a GBV_ILN_110 | ||
| 912 | |a GBV_ILN_120 | ||
| 912 | |a GBV_ILN_138 | ||
| 912 | |a GBV_ILN_150 | ||
| 912 | |a GBV_ILN_151 | ||
| 912 | |a GBV_ILN_152 | ||
| 912 | |a GBV_ILN_161 | ||
| 912 | |a GBV_ILN_170 | ||
| 912 | |a GBV_ILN_187 | ||
| 912 | |a GBV_ILN_213 | ||
| 912 | |a GBV_ILN_224 | ||
| 912 | |a GBV_ILN_230 | ||
| 912 | |a GBV_ILN_285 | ||
| 912 | |a GBV_ILN_293 | ||
| 912 | |a GBV_ILN_370 | ||
| 912 | |a GBV_ILN_602 | ||
| 912 | |a GBV_ILN_647 | ||
| 912 | |a GBV_ILN_702 | ||
| 912 | |a GBV_ILN_2001 | ||
| 912 | |a GBV_ILN_2003 | ||
| 912 | |a GBV_ILN_2004 | ||
| 912 | |a GBV_ILN_2005 | ||
| 912 | |a GBV_ILN_2006 | ||
| 912 | |a GBV_ILN_2007 | ||
| 912 | |a GBV_ILN_2009 | ||
| 912 | |a GBV_ILN_2010 | ||
| 912 | |a GBV_ILN_2011 | ||
| 912 | |a GBV_ILN_2014 | ||
| 912 | |a GBV_ILN_2015 | ||
| 912 | |a GBV_ILN_2020 | ||
| 912 | |a GBV_ILN_2021 | ||
| 912 | |a GBV_ILN_2025 | ||
| 912 | |a GBV_ILN_2026 | ||
| 912 | |a GBV_ILN_2027 | ||
| 912 | |a GBV_ILN_2031 | ||
| 912 | |a GBV_ILN_2034 | ||
| 912 | |a GBV_ILN_2037 | ||
| 912 | |a GBV_ILN_2038 | ||
| 912 | |a GBV_ILN_2039 | ||
| 912 | |a GBV_ILN_2044 | ||
| 912 | |a GBV_ILN_2049 | ||
| 912 | |a GBV_ILN_2050 | ||
| 912 | |a GBV_ILN_2055 | ||
| 912 | |a GBV_ILN_2056 | ||
| 912 | |a GBV_ILN_2059 | ||
| 912 | |a GBV_ILN_2061 | ||
| 912 | |a GBV_ILN_2064 | ||
| 912 | |a GBV_ILN_2065 | ||
| 912 | |a GBV_ILN_2068 | ||
| 912 | |a GBV_ILN_2070 | ||
| 912 | |a GBV_ILN_2086 | ||
| 912 | |a GBV_ILN_2106 | ||
| 912 | |a GBV_ILN_2108 | ||
| 912 | |a GBV_ILN_2110 | ||
| 912 | |a GBV_ILN_2111 | ||
| 912 | |a GBV_ILN_2112 | ||
| 912 | |a GBV_ILN_2113 | ||
| 912 | |a GBV_ILN_2116 | ||
| 912 | |a GBV_ILN_2118 | ||
| 912 | |a GBV_ILN_2119 | ||
| 912 | |a GBV_ILN_2122 | ||
| 912 | |a GBV_ILN_2129 | ||
| 912 | |a GBV_ILN_2143 | ||
| 912 | |a GBV_ILN_2144 | ||
| 912 | |a GBV_ILN_2147 | ||
| 912 | |a GBV_ILN_2148 | ||
| 912 | |a GBV_ILN_2152 | ||
| 912 | |a GBV_ILN_2153 | ||
| 912 | |a GBV_ILN_2188 | ||
| 912 | |a GBV_ILN_2190 | ||
| 912 | |a GBV_ILN_2232 | ||
| 912 | |a GBV_ILN_2336 | ||
| 912 | |a GBV_ILN_2507 | ||
| 912 | |a GBV_ILN_2522 | ||
| 912 | |a GBV_ILN_4012 | ||
| 912 | |a GBV_ILN_4035 | ||
| 912 | |a GBV_ILN_4037 | ||
| 912 | |a GBV_ILN_4046 | ||
| 912 | |a GBV_ILN_4112 | ||
| 912 | |a GBV_ILN_4125 | ||
| 912 | |a GBV_ILN_4126 | ||
| 912 | |a GBV_ILN_4242 | ||
| 912 | |a GBV_ILN_4246 | ||
| 912 | |a GBV_ILN_4249 | ||
| 912 | |a GBV_ILN_4251 | ||
| 912 | |a GBV_ILN_4305 | ||
| 912 | |a GBV_ILN_4306 | ||
| 912 | |a GBV_ILN_4307 | ||
| 912 | |a GBV_ILN_4313 | ||
| 912 | |a GBV_ILN_4322 | ||
| 912 | |a GBV_ILN_4323 | ||
| 912 | |a GBV_ILN_4324 | ||
| 912 | |a GBV_ILN_4325 | ||
| 912 | |a GBV_ILN_4326 | ||
| 912 | |a GBV_ILN_4328 | ||
| 912 | |a GBV_ILN_4333 | ||
| 912 | |a GBV_ILN_4334 | ||
| 912 | |a GBV_ILN_4335 | ||
| 912 | |a GBV_ILN_4338 | ||
| 912 | |a GBV_ILN_4367 | ||
| 912 | |a GBV_ILN_4393 | ||
| 912 | |a GBV_ILN_4700 | ||
| 951 | |a AR | ||
| 952 | |d 15 |j 2004 |e 7 |b 01 |c 07 |h 1025-1038 | ||
| author_variant |
f p fp m j p mj mjp p w pw c w cw b p bp |
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| matchkey_str |
article:18791123:2004----::nrmlclrodnainecinipooaedppiecromnxdwtrn |
| hierarchy_sort_str |
2004 |
| publishDate |
2004 |
| allfields |
10.1016/j.jasms.2004.03.014 doi (DE-627)SPR031488765 (SPR)j.jasms.2004.03.014-e DE-627 ger DE-627 rakwb eng Pingitore, Francesco verfasserin aut Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition 2004 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © American Society for Mass Spectrometry 2004 Abstract The elimination of carbon monoxide and water from a series of protonated dipeptides, [XxxYyy + H]+, is investigated by tandem mass spectrometry experiments and density functional theory. The combined results show that CO loss occurs on the $ a_{1} $-$ y_{1} $ pathway, which begins by rearrangement of the added proton to the amide N-atom and creates the proton-bound dimer of an amino acid (Yyy) and an imine (that from Xxx residue). The loss of $ H_{2} $O is initiated from a tautomer in which the added proton has migrated to the hydroxyl group of the C-terminus, thereby promoting the formation of an ion with protonated oxazolone structure (a nominal $ b_{2} $ ion). The highest yields of [XxxYyy+H−CO]+ and [XxxYyy+H−$ H_{2} $O]+ are observed at threshold energies. As the internal energy of the protonated dipeptides increases, these primary products are depleted by consecutive dissociations yielding mostly backbone fragments. Specifically, [XxxYyy+H−CO]+ decomposes to $ y_{1} $ (protonated Yyy) and $ a_{1} $ (immonium ion of Xxx residue), while [XxxYyy+H−$ H_{2} $O]+ produces $ a_{2} $ and the immonium ions of residues Xxx ($ a_{1} $) and Yyy (“internal” immonium ion). Water loss takes place more efficiently when the more basic residue is at the C-terminal position. Increasing the basicity of the N-terminal residue enhances the extent of CO versus $ H_{2} $O loss and introduces the competitive elimination of $ NH_{3} $. The dissociations leading to eliminations of small neutrals (CO, $ H_{2} $O, etc.) generally proceed over transition states that lie higher in energy than the corresponding dissociation products. The excess energy is disposed of either in translational or rovibrational modes of the products, depending on the stability of the incipient noncovalent assemblies emerging during the cleavage of the small neutrals. Collisionally Activate Dissociation (dpeaa)DE-He213 Oxazolone (dpeaa)DE-He213 GlyGly (dpeaa)DE-He213 AlaAla (dpeaa)DE-He213 Protonated Peptide (dpeaa)DE-He213 Polce, Michael J. aut Wang, Ping aut Wesdemiotis, Chrys aut Paizs, Béla aut Enthalten in Journal of the American Society for Mass Spectrometry Washington, DC : ACS Publications, 1990 15(2004), 7 vom: 01. Juli, Seite 1025-1038 (DE-627)320598799 (DE-600)2019911-9 1879-1123 nnns volume:15 year:2004 number:7 day:01 month:07 pages:1025-1038 https://dx.doi.org/10.1016/j.jasms.2004.03.014 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_647 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2106 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 15 2004 7 01 07 1025-1038 |
| spelling |
10.1016/j.jasms.2004.03.014 doi (DE-627)SPR031488765 (SPR)j.jasms.2004.03.014-e DE-627 ger DE-627 rakwb eng Pingitore, Francesco verfasserin aut Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition 2004 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © American Society for Mass Spectrometry 2004 Abstract The elimination of carbon monoxide and water from a series of protonated dipeptides, [XxxYyy + H]+, is investigated by tandem mass spectrometry experiments and density functional theory. The combined results show that CO loss occurs on the $ a_{1} $-$ y_{1} $ pathway, which begins by rearrangement of the added proton to the amide N-atom and creates the proton-bound dimer of an amino acid (Yyy) and an imine (that from Xxx residue). The loss of $ H_{2} $O is initiated from a tautomer in which the added proton has migrated to the hydroxyl group of the C-terminus, thereby promoting the formation of an ion with protonated oxazolone structure (a nominal $ b_{2} $ ion). The highest yields of [XxxYyy+H−CO]+ and [XxxYyy+H−$ H_{2} $O]+ are observed at threshold energies. As the internal energy of the protonated dipeptides increases, these primary products are depleted by consecutive dissociations yielding mostly backbone fragments. Specifically, [XxxYyy+H−CO]+ decomposes to $ y_{1} $ (protonated Yyy) and $ a_{1} $ (immonium ion of Xxx residue), while [XxxYyy+H−$ H_{2} $O]+ produces $ a_{2} $ and the immonium ions of residues Xxx ($ a_{1} $) and Yyy (“internal” immonium ion). Water loss takes place more efficiently when the more basic residue is at the C-terminal position. Increasing the basicity of the N-terminal residue enhances the extent of CO versus $ H_{2} $O loss and introduces the competitive elimination of $ NH_{3} $. The dissociations leading to eliminations of small neutrals (CO, $ H_{2} $O, etc.) generally proceed over transition states that lie higher in energy than the corresponding dissociation products. The excess energy is disposed of either in translational or rovibrational modes of the products, depending on the stability of the incipient noncovalent assemblies emerging during the cleavage of the small neutrals. Collisionally Activate Dissociation (dpeaa)DE-He213 Oxazolone (dpeaa)DE-He213 GlyGly (dpeaa)DE-He213 AlaAla (dpeaa)DE-He213 Protonated Peptide (dpeaa)DE-He213 Polce, Michael J. aut Wang, Ping aut Wesdemiotis, Chrys aut Paizs, Béla aut Enthalten in Journal of the American Society for Mass Spectrometry Washington, DC : ACS Publications, 1990 15(2004), 7 vom: 01. Juli, Seite 1025-1038 (DE-627)320598799 (DE-600)2019911-9 1879-1123 nnns volume:15 year:2004 number:7 day:01 month:07 pages:1025-1038 https://dx.doi.org/10.1016/j.jasms.2004.03.014 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_647 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2106 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 15 2004 7 01 07 1025-1038 |
| allfields_unstemmed |
10.1016/j.jasms.2004.03.014 doi (DE-627)SPR031488765 (SPR)j.jasms.2004.03.014-e DE-627 ger DE-627 rakwb eng Pingitore, Francesco verfasserin aut Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition 2004 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © American Society for Mass Spectrometry 2004 Abstract The elimination of carbon monoxide and water from a series of protonated dipeptides, [XxxYyy + H]+, is investigated by tandem mass spectrometry experiments and density functional theory. The combined results show that CO loss occurs on the $ a_{1} $-$ y_{1} $ pathway, which begins by rearrangement of the added proton to the amide N-atom and creates the proton-bound dimer of an amino acid (Yyy) and an imine (that from Xxx residue). The loss of $ H_{2} $O is initiated from a tautomer in which the added proton has migrated to the hydroxyl group of the C-terminus, thereby promoting the formation of an ion with protonated oxazolone structure (a nominal $ b_{2} $ ion). The highest yields of [XxxYyy+H−CO]+ and [XxxYyy+H−$ H_{2} $O]+ are observed at threshold energies. As the internal energy of the protonated dipeptides increases, these primary products are depleted by consecutive dissociations yielding mostly backbone fragments. Specifically, [XxxYyy+H−CO]+ decomposes to $ y_{1} $ (protonated Yyy) and $ a_{1} $ (immonium ion of Xxx residue), while [XxxYyy+H−$ H_{2} $O]+ produces $ a_{2} $ and the immonium ions of residues Xxx ($ a_{1} $) and Yyy (“internal” immonium ion). Water loss takes place more efficiently when the more basic residue is at the C-terminal position. Increasing the basicity of the N-terminal residue enhances the extent of CO versus $ H_{2} $O loss and introduces the competitive elimination of $ NH_{3} $. The dissociations leading to eliminations of small neutrals (CO, $ H_{2} $O, etc.) generally proceed over transition states that lie higher in energy than the corresponding dissociation products. The excess energy is disposed of either in translational or rovibrational modes of the products, depending on the stability of the incipient noncovalent assemblies emerging during the cleavage of the small neutrals. Collisionally Activate Dissociation (dpeaa)DE-He213 Oxazolone (dpeaa)DE-He213 GlyGly (dpeaa)DE-He213 AlaAla (dpeaa)DE-He213 Protonated Peptide (dpeaa)DE-He213 Polce, Michael J. aut Wang, Ping aut Wesdemiotis, Chrys aut Paizs, Béla aut Enthalten in Journal of the American Society for Mass Spectrometry Washington, DC : ACS Publications, 1990 15(2004), 7 vom: 01. Juli, Seite 1025-1038 (DE-627)320598799 (DE-600)2019911-9 1879-1123 nnns volume:15 year:2004 number:7 day:01 month:07 pages:1025-1038 https://dx.doi.org/10.1016/j.jasms.2004.03.014 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_647 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2106 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 15 2004 7 01 07 1025-1038 |
| allfieldsGer |
10.1016/j.jasms.2004.03.014 doi (DE-627)SPR031488765 (SPR)j.jasms.2004.03.014-e DE-627 ger DE-627 rakwb eng Pingitore, Francesco verfasserin aut Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition 2004 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © American Society for Mass Spectrometry 2004 Abstract The elimination of carbon monoxide and water from a series of protonated dipeptides, [XxxYyy + H]+, is investigated by tandem mass spectrometry experiments and density functional theory. The combined results show that CO loss occurs on the $ a_{1} $-$ y_{1} $ pathway, which begins by rearrangement of the added proton to the amide N-atom and creates the proton-bound dimer of an amino acid (Yyy) and an imine (that from Xxx residue). The loss of $ H_{2} $O is initiated from a tautomer in which the added proton has migrated to the hydroxyl group of the C-terminus, thereby promoting the formation of an ion with protonated oxazolone structure (a nominal $ b_{2} $ ion). The highest yields of [XxxYyy+H−CO]+ and [XxxYyy+H−$ H_{2} $O]+ are observed at threshold energies. As the internal energy of the protonated dipeptides increases, these primary products are depleted by consecutive dissociations yielding mostly backbone fragments. Specifically, [XxxYyy+H−CO]+ decomposes to $ y_{1} $ (protonated Yyy) and $ a_{1} $ (immonium ion of Xxx residue), while [XxxYyy+H−$ H_{2} $O]+ produces $ a_{2} $ and the immonium ions of residues Xxx ($ a_{1} $) and Yyy (“internal” immonium ion). Water loss takes place more efficiently when the more basic residue is at the C-terminal position. Increasing the basicity of the N-terminal residue enhances the extent of CO versus $ H_{2} $O loss and introduces the competitive elimination of $ NH_{3} $. The dissociations leading to eliminations of small neutrals (CO, $ H_{2} $O, etc.) generally proceed over transition states that lie higher in energy than the corresponding dissociation products. The excess energy is disposed of either in translational or rovibrational modes of the products, depending on the stability of the incipient noncovalent assemblies emerging during the cleavage of the small neutrals. Collisionally Activate Dissociation (dpeaa)DE-He213 Oxazolone (dpeaa)DE-He213 GlyGly (dpeaa)DE-He213 AlaAla (dpeaa)DE-He213 Protonated Peptide (dpeaa)DE-He213 Polce, Michael J. aut Wang, Ping aut Wesdemiotis, Chrys aut Paizs, Béla aut Enthalten in Journal of the American Society for Mass Spectrometry Washington, DC : ACS Publications, 1990 15(2004), 7 vom: 01. Juli, Seite 1025-1038 (DE-627)320598799 (DE-600)2019911-9 1879-1123 nnns volume:15 year:2004 number:7 day:01 month:07 pages:1025-1038 https://dx.doi.org/10.1016/j.jasms.2004.03.014 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_647 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2106 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 15 2004 7 01 07 1025-1038 |
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10.1016/j.jasms.2004.03.014 doi (DE-627)SPR031488765 (SPR)j.jasms.2004.03.014-e DE-627 ger DE-627 rakwb eng Pingitore, Francesco verfasserin aut Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition 2004 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © American Society for Mass Spectrometry 2004 Abstract The elimination of carbon monoxide and water from a series of protonated dipeptides, [XxxYyy + H]+, is investigated by tandem mass spectrometry experiments and density functional theory. The combined results show that CO loss occurs on the $ a_{1} $-$ y_{1} $ pathway, which begins by rearrangement of the added proton to the amide N-atom and creates the proton-bound dimer of an amino acid (Yyy) and an imine (that from Xxx residue). The loss of $ H_{2} $O is initiated from a tautomer in which the added proton has migrated to the hydroxyl group of the C-terminus, thereby promoting the formation of an ion with protonated oxazolone structure (a nominal $ b_{2} $ ion). The highest yields of [XxxYyy+H−CO]+ and [XxxYyy+H−$ H_{2} $O]+ are observed at threshold energies. As the internal energy of the protonated dipeptides increases, these primary products are depleted by consecutive dissociations yielding mostly backbone fragments. Specifically, [XxxYyy+H−CO]+ decomposes to $ y_{1} $ (protonated Yyy) and $ a_{1} $ (immonium ion of Xxx residue), while [XxxYyy+H−$ H_{2} $O]+ produces $ a_{2} $ and the immonium ions of residues Xxx ($ a_{1} $) and Yyy (“internal” immonium ion). Water loss takes place more efficiently when the more basic residue is at the C-terminal position. Increasing the basicity of the N-terminal residue enhances the extent of CO versus $ H_{2} $O loss and introduces the competitive elimination of $ NH_{3} $. The dissociations leading to eliminations of small neutrals (CO, $ H_{2} $O, etc.) generally proceed over transition states that lie higher in energy than the corresponding dissociation products. The excess energy is disposed of either in translational or rovibrational modes of the products, depending on the stability of the incipient noncovalent assemblies emerging during the cleavage of the small neutrals. Collisionally Activate Dissociation (dpeaa)DE-He213 Oxazolone (dpeaa)DE-He213 GlyGly (dpeaa)DE-He213 AlaAla (dpeaa)DE-He213 Protonated Peptide (dpeaa)DE-He213 Polce, Michael J. aut Wang, Ping aut Wesdemiotis, Chrys aut Paizs, Béla aut Enthalten in Journal of the American Society for Mass Spectrometry Washington, DC : ACS Publications, 1990 15(2004), 7 vom: 01. Juli, Seite 1025-1038 (DE-627)320598799 (DE-600)2019911-9 1879-1123 nnns volume:15 year:2004 number:7 day:01 month:07 pages:1025-1038 https://dx.doi.org/10.1016/j.jasms.2004.03.014 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_647 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2106 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 15 2004 7 01 07 1025-1038 |
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Enthalten in Journal of the American Society for Mass Spectrometry 15(2004), 7 vom: 01. Juli, Seite 1025-1038 volume:15 year:2004 number:7 day:01 month:07 pages:1025-1038 |
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Enthalten in Journal of the American Society for Mass Spectrometry 15(2004), 7 vom: 01. Juli, Seite 1025-1038 volume:15 year:2004 number:7 day:01 month:07 pages:1025-1038 |
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Collisionally Activate Dissociation Oxazolone GlyGly AlaAla Protonated Peptide |
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Pingitore, Francesco @@aut@@ Polce, Michael J. @@aut@@ Wang, Ping @@aut@@ Wesdemiotis, Chrys @@aut@@ Paizs, Béla @@aut@@ |
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The combined results show that CO loss occurs on the $ a_{1} $-$ y_{1} $ pathway, which begins by rearrangement of the added proton to the amide N-atom and creates the proton-bound dimer of an amino acid (Yyy) and an imine (that from Xxx residue). The loss of $ H_{2} $O is initiated from a tautomer in which the added proton has migrated to the hydroxyl group of the C-terminus, thereby promoting the formation of an ion with protonated oxazolone structure (a nominal $ b_{2} $ ion). The highest yields of [XxxYyy+H−CO]+ and [XxxYyy+H−$ H_{2} $O]+ are observed at threshold energies. As the internal energy of the protonated dipeptides increases, these primary products are depleted by consecutive dissociations yielding mostly backbone fragments. Specifically, [XxxYyy+H−CO]+ decomposes to $ y_{1} $ (protonated Yyy) and $ a_{1} $ (immonium ion of Xxx residue), while [XxxYyy+H−$ H_{2} $O]+ produces $ a_{2} $ and the immonium ions of residues Xxx ($ a_{1} $) and Yyy (“internal” immonium ion). Water loss takes place more efficiently when the more basic residue is at the C-terminal position. Increasing the basicity of the N-terminal residue enhances the extent of CO versus $ H_{2} $O loss and introduces the competitive elimination of $ NH_{3} $. The dissociations leading to eliminations of small neutrals (CO, $ H_{2} $O, etc.) generally proceed over transition states that lie higher in energy than the corresponding dissociation products. 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Pingitore, Francesco |
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Pingitore, Francesco misc Collisionally Activate Dissociation misc Oxazolone misc GlyGly misc AlaAla misc Protonated Peptide Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition |
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Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition Collisionally Activate Dissociation (dpeaa)DE-He213 Oxazolone (dpeaa)DE-He213 GlyGly (dpeaa)DE-He213 AlaAla (dpeaa)DE-He213 Protonated Peptide (dpeaa)DE-He213 |
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Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition |
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Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition |
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Pingitore, Francesco |
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Pingitore, Francesco Polce, Michael J. Wang, Ping Wesdemiotis, Chrys Paizs, Béla |
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intramolecular condensation reactions in protonated dipeptides: carbon monoxide, water, and ammonia losses in competition |
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Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition |
| abstract |
Abstract The elimination of carbon monoxide and water from a series of protonated dipeptides, [XxxYyy + H]+, is investigated by tandem mass spectrometry experiments and density functional theory. The combined results show that CO loss occurs on the $ a_{1} $-$ y_{1} $ pathway, which begins by rearrangement of the added proton to the amide N-atom and creates the proton-bound dimer of an amino acid (Yyy) and an imine (that from Xxx residue). The loss of $ H_{2} $O is initiated from a tautomer in which the added proton has migrated to the hydroxyl group of the C-terminus, thereby promoting the formation of an ion with protonated oxazolone structure (a nominal $ b_{2} $ ion). The highest yields of [XxxYyy+H−CO]+ and [XxxYyy+H−$ H_{2} $O]+ are observed at threshold energies. As the internal energy of the protonated dipeptides increases, these primary products are depleted by consecutive dissociations yielding mostly backbone fragments. Specifically, [XxxYyy+H−CO]+ decomposes to $ y_{1} $ (protonated Yyy) and $ a_{1} $ (immonium ion of Xxx residue), while [XxxYyy+H−$ H_{2} $O]+ produces $ a_{2} $ and the immonium ions of residues Xxx ($ a_{1} $) and Yyy (“internal” immonium ion). Water loss takes place more efficiently when the more basic residue is at the C-terminal position. Increasing the basicity of the N-terminal residue enhances the extent of CO versus $ H_{2} $O loss and introduces the competitive elimination of $ NH_{3} $. The dissociations leading to eliminations of small neutrals (CO, $ H_{2} $O, etc.) generally proceed over transition states that lie higher in energy than the corresponding dissociation products. The excess energy is disposed of either in translational or rovibrational modes of the products, depending on the stability of the incipient noncovalent assemblies emerging during the cleavage of the small neutrals. © American Society for Mass Spectrometry 2004 |
| abstractGer |
Abstract The elimination of carbon monoxide and water from a series of protonated dipeptides, [XxxYyy + H]+, is investigated by tandem mass spectrometry experiments and density functional theory. The combined results show that CO loss occurs on the $ a_{1} $-$ y_{1} $ pathway, which begins by rearrangement of the added proton to the amide N-atom and creates the proton-bound dimer of an amino acid (Yyy) and an imine (that from Xxx residue). The loss of $ H_{2} $O is initiated from a tautomer in which the added proton has migrated to the hydroxyl group of the C-terminus, thereby promoting the formation of an ion with protonated oxazolone structure (a nominal $ b_{2} $ ion). The highest yields of [XxxYyy+H−CO]+ and [XxxYyy+H−$ H_{2} $O]+ are observed at threshold energies. As the internal energy of the protonated dipeptides increases, these primary products are depleted by consecutive dissociations yielding mostly backbone fragments. Specifically, [XxxYyy+H−CO]+ decomposes to $ y_{1} $ (protonated Yyy) and $ a_{1} $ (immonium ion of Xxx residue), while [XxxYyy+H−$ H_{2} $O]+ produces $ a_{2} $ and the immonium ions of residues Xxx ($ a_{1} $) and Yyy (“internal” immonium ion). Water loss takes place more efficiently when the more basic residue is at the C-terminal position. Increasing the basicity of the N-terminal residue enhances the extent of CO versus $ H_{2} $O loss and introduces the competitive elimination of $ NH_{3} $. The dissociations leading to eliminations of small neutrals (CO, $ H_{2} $O, etc.) generally proceed over transition states that lie higher in energy than the corresponding dissociation products. The excess energy is disposed of either in translational or rovibrational modes of the products, depending on the stability of the incipient noncovalent assemblies emerging during the cleavage of the small neutrals. © American Society for Mass Spectrometry 2004 |
| abstract_unstemmed |
Abstract The elimination of carbon monoxide and water from a series of protonated dipeptides, [XxxYyy + H]+, is investigated by tandem mass spectrometry experiments and density functional theory. The combined results show that CO loss occurs on the $ a_{1} $-$ y_{1} $ pathway, which begins by rearrangement of the added proton to the amide N-atom and creates the proton-bound dimer of an amino acid (Yyy) and an imine (that from Xxx residue). The loss of $ H_{2} $O is initiated from a tautomer in which the added proton has migrated to the hydroxyl group of the C-terminus, thereby promoting the formation of an ion with protonated oxazolone structure (a nominal $ b_{2} $ ion). The highest yields of [XxxYyy+H−CO]+ and [XxxYyy+H−$ H_{2} $O]+ are observed at threshold energies. As the internal energy of the protonated dipeptides increases, these primary products are depleted by consecutive dissociations yielding mostly backbone fragments. Specifically, [XxxYyy+H−CO]+ decomposes to $ y_{1} $ (protonated Yyy) and $ a_{1} $ (immonium ion of Xxx residue), while [XxxYyy+H−$ H_{2} $O]+ produces $ a_{2} $ and the immonium ions of residues Xxx ($ a_{1} $) and Yyy (“internal” immonium ion). Water loss takes place more efficiently when the more basic residue is at the C-terminal position. Increasing the basicity of the N-terminal residue enhances the extent of CO versus $ H_{2} $O loss and introduces the competitive elimination of $ NH_{3} $. The dissociations leading to eliminations of small neutrals (CO, $ H_{2} $O, etc.) generally proceed over transition states that lie higher in energy than the corresponding dissociation products. The excess energy is disposed of either in translational or rovibrational modes of the products, depending on the stability of the incipient noncovalent assemblies emerging during the cleavage of the small neutrals. © American Society for Mass Spectrometry 2004 |
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| title_short |
Intramolecular condensation reactions in protonated dipeptides: Carbon monoxide, water, and ammonia losses in competition |
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https://dx.doi.org/10.1016/j.jasms.2004.03.014 |
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Polce, Michael J. Wang, Ping Wesdemiotis, Chrys Paizs, Béla |
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10.1016/j.jasms.2004.03.014 |
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2024-07-03T23:57:43.994Z |
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| score |
7.400154 |