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Article: Solvent-assisted rearrangements between tautomers of protonated peptides
Title | Solvent-assisted rearrangements between tautomers of protonated peptides |
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Authors | |
Issue Date | 2000 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/jpca |
Citation | Journal Of Physical Chemistry A, 2000, v. 104 n. 21, p. 5023-5028 How to Cite? |
Abstract | The presence of an interacting water or methanol molecule has been shown to catalyze the 1,3-proton shift in a peptide linkage between the tautomers of protonated formamide and glycylglycylglycine. Density functional theory calculations at the B3LYP/6-31++G(d,p) level of theory show that, for glycylglycylglycine, the forward barrier of this shift decreases from a free energy at 298 K of 39.6 kcal/mol in the absence of solvent to 26.7 kcal/mol in the presence of water and to 22.0 kcal/mol in the presence of methanol. Protonation at the amide nitrogen of the second residue results in a large increase in the C-N bond distance from 1.336 to 1.519 Å, whereas protonation at the carbonyl oxygen leads to a decrease in the C-N bond distance from 1.336 to 1.321 Å. Solvent-catalyzed tautomerism may play an important role in the fragmentation of electrosprayed, protonated peptides in the gas phase. © 2000 American Chemical Society. |
Persistent Identifier | http://hdl.handle.net/10722/167637 |
ISSN | 2023 Impact Factor: 2.7 2023 SCImago Journal Rankings: 0.604 |
References |
DC Field | Value | Language |
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dc.contributor.author | Rodriquez, CF | en_US |
dc.contributor.author | Cunje, A | en_US |
dc.contributor.author | Shoeib, T | en_US |
dc.contributor.author | Chu, IK | en_US |
dc.contributor.author | Hopkinson, AC | en_US |
dc.contributor.author | Siu, KWM | en_US |
dc.date.accessioned | 2012-10-08T03:09:19Z | - |
dc.date.available | 2012-10-08T03:09:19Z | - |
dc.date.issued | 2000 | en_US |
dc.identifier.citation | Journal Of Physical Chemistry A, 2000, v. 104 n. 21, p. 5023-5028 | en_US |
dc.identifier.issn | 1089-5639 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/167637 | - |
dc.description.abstract | The presence of an interacting water or methanol molecule has been shown to catalyze the 1,3-proton shift in a peptide linkage between the tautomers of protonated formamide and glycylglycylglycine. Density functional theory calculations at the B3LYP/6-31++G(d,p) level of theory show that, for glycylglycylglycine, the forward barrier of this shift decreases from a free energy at 298 K of 39.6 kcal/mol in the absence of solvent to 26.7 kcal/mol in the presence of water and to 22.0 kcal/mol in the presence of methanol. Protonation at the amide nitrogen of the second residue results in a large increase in the C-N bond distance from 1.336 to 1.519 Å, whereas protonation at the carbonyl oxygen leads to a decrease in the C-N bond distance from 1.336 to 1.321 Å. Solvent-catalyzed tautomerism may play an important role in the fragmentation of electrosprayed, protonated peptides in the gas phase. © 2000 American Chemical Society. | en_US |
dc.language | eng | en_US |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/jpca | en_US |
dc.relation.ispartof | Journal of Physical Chemistry A | en_US |
dc.title | Solvent-assisted rearrangements between tautomers of protonated peptides | en_US |
dc.type | Article | en_US |
dc.identifier.email | Chu, IK:ivankchu@hku.hk | en_US |
dc.identifier.authority | Chu, IK=rp00683 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1021/jp9940203 | - |
dc.identifier.scopus | eid_2-s2.0-0033732290 | en_US |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-0033732290&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 104 | en_US |
dc.identifier.issue | 21 | en_US |
dc.identifier.spage | 5023 | en_US |
dc.identifier.epage | 5028 | en_US |
dc.publisher.place | United States | en_US |
dc.identifier.scopusauthorid | Rodriquez, CF=7004085075 | en_US |
dc.identifier.scopusauthorid | Cunje, A=6602535833 | en_US |
dc.identifier.scopusauthorid | Shoeib, T=6603516521 | en_US |
dc.identifier.scopusauthorid | Chu, IK=7103327484 | en_US |
dc.identifier.scopusauthorid | Hopkinson, AC=15067169300 | en_US |
dc.identifier.scopusauthorid | Siu, KWM=8967015800 | en_US |
dc.identifier.issnl | 1089-5639 | - |