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Article: Solvent-assisted rearrangements between tautomers of protonated peptides

TitleSolvent-assisted rearrangements between tautomers of protonated peptides
Authors
Issue Date2000
PublisherAmerican 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?
AbstractThe 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 Identifierhttp://hdl.handle.net/10722/167637
ISSN
2015 Impact Factor: 2.883
2015 SCImago Journal Rankings: 1.231
References

 

DC FieldValueLanguage
dc.contributor.authorRodriquez, CFen_US
dc.contributor.authorCunje, Aen_US
dc.contributor.authorShoeib, Ten_US
dc.contributor.authorChu, IKen_US
dc.contributor.authorHopkinson, ACen_US
dc.contributor.authorSiu, KWMen_US
dc.date.accessioned2012-10-08T03:09:19Z-
dc.date.available2012-10-08T03:09:19Z-
dc.date.issued2000en_US
dc.identifier.citationJournal Of Physical Chemistry A, 2000, v. 104 n. 21, p. 5023-5028en_US
dc.identifier.issn1089-5639en_US
dc.identifier.urihttp://hdl.handle.net/10722/167637-
dc.description.abstractThe 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.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jpcaen_US
dc.relation.ispartofJournal of Physical Chemistry Aen_US
dc.titleSolvent-assisted rearrangements between tautomers of protonated peptidesen_US
dc.typeArticleen_US
dc.identifier.emailChu, IK:ivankchu@hku.hken_US
dc.identifier.authorityChu, IK=rp00683en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/jp9940203-
dc.identifier.scopuseid_2-s2.0-0033732290en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0033732290&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume104en_US
dc.identifier.issue21en_US
dc.identifier.spage5023en_US
dc.identifier.epage5028en_US
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridRodriquez, CF=7004085075en_US
dc.identifier.scopusauthoridCunje, A=6602535833en_US
dc.identifier.scopusauthoridShoeib, T=6603516521en_US
dc.identifier.scopusauthoridChu, IK=7103327484en_US
dc.identifier.scopusauthoridHopkinson, AC=15067169300en_US
dc.identifier.scopusauthoridSiu, KWM=8967015800en_US

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