Conformation of the Na+ complex of antamanide in solution

Иванов, В. Т.; Мирошников, А. И.; Абдуллаев, Н. Д.; Senyavina, L. B.; Архипова, С. Ф.; Uvarova, N. N.; Khalilulina, K. Kh.; Bystrov, V. F.; Ovchinnikov, Yu.A.

doi:10.1016/0006-291x(71)90538-9

Cited by 57 publications

(21 citation statements)

References 15 publications

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“…Since the barrier to rotation about the peptide * Dedicated to our late colleague, Dr. Simon C. K. Wong, who was a gentleman, a scholar, and a scientist. bond is estimated to be at least [15][16][17][18][19][20], different cyclic peptide conformations resulting from the presence of cis-and trans-X-Pro peptide bonds yield separate NMR spectra, thus permitting direct determination of the populations of the conformers present in solution under different conditions (e.g., various solvents or temperatures).…”

mentioning

confidence: 99%

“…Furthermore, the rotational potential about the Pro Ca C=O bond is characterized (10) by two regions of low conformational energy, with minima at cis' (Pro 4 -125°) and trans' (Pro 4 -3000). If rotational isomers about the Pro Ca C=O bond are includedll, the number of possible conformers increases to 16, of which only four have C3-symmetry: those with three cis' bonds and either three cis or three trans Gly-Pro peptide bonds; and those with three trans' bonds, and either three cis or three trans Gly-Pro peptide bonds. The NMR spectrum observed in CD2Cl2 can be assigned with reasonable certainty to a single C3-symmetric conformer on the basis of the following considerations.…”

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confidence: 99%

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Conformational Interconversions of the Cyclic Hexapeptide Cyclo(Pro-Gly) ₃

Deber

Torchia²,

Wong

et al. 1972

Proc. Natl. Acad. Sci. U.S.A.

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A cyclic hexapeptide, cyclo(Pro-Gly-ProGly-Pro-Gly), hasbeen synthesized; its solution conformations were examined by 220-MHz nuclear magnetic resonance spectroscopy. The solution structures have been deduced, and shown to vary as a function of solvent polarity. In addition, it has been found that this cyclic peptide binds alkali metal cations. While the predominant conformation of this cyclic peptide is 3-fold symmetric in the apolar solvent methylene chloride, an asymmetric structure is preferred in some polar solvents (water, dimethylsulfoxide). However, addition of alkali metal salts, such as sodium thiocyanate, to dimethylsulfoxide solutions of the peptide shifts the conformational equilibrium in favor of a second type of C3-symmetric structure, presumably the result of the formation of a stable peptide-metal ion complex. Nuclear magnetic resonance data suggest that the peptide in methylene chloride solution takes up a conformation containing three cis' Pro CaC=O bonds and three cis Gly-Pro peptide bonds; that water and dimethylsulfoxide stabilize a conformer in which one (or two) sets of such bonds of a given Pro-Gly unit have undergone interconversion to trans'/trans forms; and that alkali metal cations complex the cyclic peptide in a Cs-symmetric all-trans'/trans structure.The biological activity and structural simplicity of many cyclic peptides have generated considerable interest in the determination of their conformations, with the ultimate goal of ascertaining structure-function relationships. Highresolution nuclear magnetic resonance (NMR) spectroscopy, useful for the study of solution conformations of cyclic peptides, can provide information for structural determinations (1,2).Many naturally-occurring cyclic peptides contain proline, and it is believed that investigations of synthetic prolinecontaining cyclic peptides composed of repeating oligopeptide units (3-5) may clarify the structural role of the prolyl residue in biologically active cyclic peptides. An additional advantage of the investigation of proline peptides is that the number of possible conformers of the peptide backbone is limited by the restrictions to rotation about the N-CCa bond of the prolyl residues. Another consideration is the recent demonstration of the presence of cis-and trane-X-Pro peptide bonds (where X is any amino-acid residue preceeding a proline residue), in both linear (6-8) and cyclic (4, 5) proline-containing peptides. Since the barrier to rotation about the peptide

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mentioning

confidence: 99%

mentioning

confidence: 99%

Conformational Interconversions of the Cyclic Hexapeptide Cyclo(Pro-Gly) ₃

Deber

Torchia²,

Wong

et al. 1972

Proc. Natl. Acad. Sci. U.S.A.

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“…Langsames Eindiffun dieren von M ethanol in die Lösung im Exsikkator führte nach einigen Tagen zur K ristallisation von (2).…”

Section: Syntheseunclassified

“…Ganz allgemein hängt der Transport von M etallionen in Flüssigkeiten und durch Mem branen im K örper weitgehend vom Komplexie rungsvermögen der Am inosäuren und Peptide ab. Auch die W irksamkeit von cyclischen Peptidanti biotika läßt sich durch Synthese und C harakteri sierung geeigneter M etall-Peptidkomplexe weitge hend modellieren [2].…”

unclassified

Bindung von Metall-Ionen an Dipeptide: Struktur von Thallium(I)-(3-benzyl-6-carboxylatomethyl-2,5-diketopiperazin) / Binding of Metal Ions by Dipeptides: Structure of Thallium(I) 3-Benzyl-6-carboxylatomethyl-2,5-diketopiperazine

Mikulcik

Bissinger

Riede

et al. 1992

Zeitschrift Für Naturforschung B

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Ester cleavage of aspartam e (L-a-aspartyl-L-phenylalanine methylester) (1), by equimolar quantities of thallium ethoxide is accompanied by intramolecular cyclisation to give thallium 3-benzyl-6-(carboxylatomethyl)-2,5-dioxopiperazine (2). The solid state structure of the crys talline product was determined by single-crystal X-ray diffraction analysis. The cations were found to form four short and four elongated contacts to seven oxygen atom s and one nitrogen atom of a total of six neighbouring 3-benzyl-6-(carboxylatomethyl)-2,5-dioxopiperazine an ions. There are inter-anionic hydrogen bonds only between the imino groups and the carbonyl oxygen atoms ( 0 3, 0 4 ), featuring a pattern similar to that found for cytosine-guanosine contacts in DNA. Das in kristalliner Form erhaltene Produkt war jedoch nicht das erwartete Thallium -L-a-aspartyl-L-phenylalaninat, sondern stellte sich als Thal-

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“…Valinomycingruppe -Valinomycin (l l, 13), Enniatin A, B und C (4,14), Makrotetrolide (15,16,17), Antamanid (18,19,20) und Beauvericin (11) -sind positiv geladen (11); monobasische Säuren der Nigericin-Gruppe -Nigericin (21,22), Monensin (21,23), Grisorixin (24,25), Dianemycin (21,26), X-206 (27), X-537A (28-31) -elektrisch neutral (l 1). Acyclische Antibiotika bauen bei der Komplexbüdung einen Pseudocyclus um das Kation (32).…”

Section: Metallkomplexe Makrocyclischer Neutraler Moleküle Derunclassified

Ammoniumselektive Disk-Elektrode mit dem Carrier-Antibiotikum Nonactin. Verfahren zur kontinuierlichen enzymatischen Elektroanalyse von Harnstoff, I. Mitteilung

Schindler¹,

Schindler²,

Aziz³

1978

Clinical Chemistry and Laboratory Medicine

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Zusammenfassung: Die Membran der beschriebenen ammoniumselektiven Disk-Elektrode besteht aus einer Polyvinylchlorid-Matrix mit der aktiven Phase Nonactin in Tris (2-ethylhexyl)-phosphat und Diphenylether als ioncnselektivem Kunststoff, der einerseits mit der Stirnfläche eines acrylglasummantelten Platin-Drahtes und andererseits mit der Meßflüssigkeit Kontakt hat, wobei sich an dieser Phasengrenze eine Potentialdifferenz ausbilden kann. Ammonium-selective disc-electrode with the carrier-antibiotic nonactin. A method for the continuous enzymatic, electrochemical determination of urea, LSummary: An ammonium-selective disc-electrode is described; the membrane consists of a polyvinylchloride-matrix with an active phase of nonactin in tris (2-ethylhexyl)phosphate and diphenyl ether as the ion-selective plastic. One side of the membrane is in contact with the solution to be measured and the other with the front surface of a platinum wire, which is enclosed in acrylic glass. This arrangement results in a very low drift potential. Einleitung

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Conformation of the Na+ complex of antamanide in solution

Cited by 57 publications

References 15 publications

Conformational Interconversions of the Cyclic Hexapeptide Cyclo(Pro-Gly) ₃

Conformational Interconversions of the Cyclic Hexapeptide Cyclo(Pro-Gly) ₃

Bindung von Metall-Ionen an Dipeptide: Struktur von Thallium(I)-(3-benzyl-6-carboxylatomethyl-2,5-diketopiperazin) / Binding of Metal Ions by Dipeptides: Structure of Thallium(I) 3-Benzyl-6-carboxylatomethyl-2,5-diketopiperazine

Ammoniumselektive Disk-Elektrode mit dem Carrier-Antibiotikum Nonactin. Verfahren zur kontinuierlichen enzymatischen Elektroanalyse von Harnstoff, I. Mitteilung

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Conformation of the Na+ complex of antamanide in solution

Cited by 57 publications

References 15 publications

Conformational Interconversions of the Cyclic Hexapeptide Cyclo(Pro-Gly) 3

Conformational Interconversions of the Cyclic Hexapeptide Cyclo(Pro-Gly) 3

Bindung von Metall-Ionen an Dipeptide: Struktur von Thallium(I)-(3-benzyl-6-carboxylatomethyl-2,5-diketopiperazin) / Binding of Metal Ions by Dipeptides: Structure of Thallium(I) 3-Benzyl-6-carboxylatomethyl-2,5-diketopiperazine

Ammoniumselektive Disk-Elektrode mit dem Carrier-Antibiotikum Nonactin. Verfahren zur kontinuierlichen enzymatischen Elektroanalyse von Harnstoff, I. Mitteilung

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Conformational Interconversions of the Cyclic Hexapeptide Cyclo(Pro-Gly) ₃

Conformational Interconversions of the Cyclic Hexapeptide Cyclo(Pro-Gly) ₃