1978
DOI: 10.1021/ja00472a042
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Conformational and ion binding studies of a cyclic pentapeptide. Evidence for .beta. and .gamma. turns in solution

Abstract: The cyclic pentapeptide, oWo-(glycyl-L-prolylglycyl-D-alanyl-L-prolyl) [cyc7o-(Glyi-Pro-Gly2-D-Ala-Pro)], has been synthesized and studied by 'H and 13C nuclear magnetic resonance (NMR) and circular dichroism (CD). We find that the predominant conformation in chloroform, acetonitrile, dimethyl sulfoxide, and water contains all trans peptide bonds and displays two N-H's (those of Gly-1 and D-Ala) which by the usual criteria (solvent, concentration, and temperature independence of 'H chemical shifts) do not part… Show more

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Cited by 113 publications
(47 citation statements)
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“…However, shorter turns (1-3 turns, or -y-turns) have been predicted (Nemethy and Printz, 1972) and observed in synthetic oligopeptides (Madison et al, 1974;Pease and Watson, 1978;Thompson and Gierasch, 1984) and in soluble proteins (Mathews, 1972). Although their frequency in the latter is low, the constraints existing in membrane proteins may be significantly different.…”
Section: Introductionmentioning
confidence: 99%
“…However, shorter turns (1-3 turns, or -y-turns) have been predicted (Nemethy and Printz, 1972) and observed in synthetic oligopeptides (Madison et al, 1974;Pease and Watson, 1978;Thompson and Gierasch, 1984) and in soluble proteins (Mathews, 1972). Although their frequency in the latter is low, the constraints existing in membrane proteins may be significantly different.…”
Section: Introductionmentioning
confidence: 99%
“…In contrast, it has been established that pentapeptides like cyc/o(Gly-Pro-Gly-D-Ala-Pro) can adopt a conformation containing both ß and y turns. In solution, this particular peptide resides predominantly in a ßll/y turn conformation in a variety of solvent and temperature combinations as determined by NMR and CD [20]. An Xray crystal structure supported these findings in the solid state [21].…”
Section: Peptide Macrocyclesmentioning
confidence: 62%
“…To synthesize the third generation of compounds containing the extra methyl group within the peptide macrocycle, perform the same conformational analysis as mentioned above, and submit all prospective candidates for biological assays (months [13][14][15][16][17][18][19][20][21][22][23][24].…”
Section: Taskmentioning
confidence: 99%
“…Structure of the cyclic pentapeptide, cyclo(Gly-LPro-Gly-D-Ala-L-Pro), as determined by X-ray crystallography 4 and NMR. 5,6 Note that this canonical cyclic pentapeptide is essentially a fusion of a b-turn (green) and a c-turn (red) with their stabilizing 1-4 and 1-3 hydrogen bonds, respectively. Adapted from Ref.…”
Section: 3mentioning
confidence: 99%