Hydrogen bonding and isomerization in thioamide peptide derivatives

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DOIResolve DOI: http://doi.org/10.1016/0584-8539(95)01448-9
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TypeArticle
Journal titleSpectrochimica Acta Part A : Molecular and Biomolecular Spectroscopy
ISSN1386-1425
Volume51
Issue8
Pages13991412; # of pages: 14
SubjectHydrogen bond; Isomerism; Peptide; Thiopeptide; OM
AbstractThe conformations of fourteen thiopeptides in three solvents (acetonitrile, methylene chloride, DMSO) are discussed as inferred by interpretation of the amide infrared absorptions. The spectra indicate that the enhanced acidity of the thioamide NH proton (and hence the stronger hydrogen-bonding donor potential) promotes the formation of C5 ring structures that are not often found in unsubstituted peptides, and strong C(S)NH → OC hydrogen bonds render both C, (γ-turn) and C10 (β-turn) structures more stable than their oxoamide counterparts. The ability of infrared spectra to discriminate among C5, C7, and C10 structures is evaluated and discussed.
Publication date
PublisherElsevier Science B.V.
LanguageEnglish
AffiliationNRC Institute for Biodiagnostics; National Research Council Canada
Peer reviewedYes
NRC number170
NPARC number9147862
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Record identifierfe372724-8359-4b4d-bde1-19d7cc21a2de
Record created2009-06-25
Record modified2016-12-02
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