Turns in small cyclic peptides — can infrared spectroscopy detect and discriminate amongst them?

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DOIResolve DOI: http://doi.org/10.1016/0022-2860(94)08235-9
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TypeArticle
Journal titleJournal of Molecular Structure
ISSN0022-2860
Volume324
Issue1-2
Pages143150; # of pages: 8
Subjectϵ-Aca = ϵ-aminocaproic acid; δ-Ava = δ-aminovaleric acid; vCPA = cyclo[ϵ-aminocaproyl-l-prolyl-l-alanine]; CPTOBz = cyclo[ϵ-aminocaproyl-l-prolyl-l-threonineOBz], (CPA)2; CPTOBz = cyclo[ϵ-aminocaproyl-l-prolyl-l-threonineOBz], (CPA)2; CPA)2 = cyclo[ϵ-aminocaproyl-l-prolyl-l-alanyl-ϵ-aminocaproyl-l-prolyl-l-alanine]
AbstractInfrared spectra are reported in the amide I absorption region for some cyclic peptides of the general formula cyclo[ϵ-Aca-Pro-Xxx] (ϵ-Aca = ϵ-aminocaproyl; Xxx = Ala, ThrOBz) and the corresponding “dimers” cyclo[ϵ-Aca-Pro-Xxx-ϵ-Aca-Pro-Xxx] dissolved in D₂O and acetonitrile. The acetonitrile solution spectra are very different from those measured in D₂O. In particular, the D₂O solution spectra exhibit amide I absorptions at exceptionally low frequencies (1595–1600 cm⁻¹). The infrared spectra are interpreted as indicating an unusual D₂O solution structure involving three-centered hydrogen bonding to the Aca carbonyl group, two amide protons interacting with the C=O group to simultaneously close both a γ-turn and a β-turn. The acetonitrile solution spectra are interpreted as reflecting hydrogen-bonding characteristics of a β-turn, with certain compounds also showing absorptions that suggest the presence of other hydrogen-bonded (γ-turn) conformers.
Publication date
PublisherElsevier Science B.V.
LanguageEnglish
AffiliationNational Research Council Canada; NRC Institute for Biodiagnostics
Peer reviewedYes
NRC number105
NPARC number9742634
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Record identifier598a5285-dc45-4997-a3bc-f6da922ad65c
Record created2009-07-17
Record modified2016-12-08
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