Carbon-13 nuclear magnetic resonance studies of the conformations of cyclic dipeptides

Deslauriers, R.; Grzonka, Zbigniew; Schaumburg, Kjeld; Shiba, Tetsuo; Walter, Roderich

doi:10.1021/ja00851a011

Cited by 76 publications

(27 citation statements)

References 11 publications

(14 reference statements)

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“…LVP, AVP, oxytocin, PLG, Z-Pro-Leu-Gly-NH2, Leu-Gly-NH2-AcOH, Z-Leu-Gly-NH2, D-Leu-Gly-NH2, and thyrotropin releasing hormone (<Glu-His-Pro-NH2) were from the same batches used in earlier studies (19,22), as were ProLys-Gly-NH2, <Glu-Leu-Gly-NH2 (22) (28), and the diketopiperazine of Leu-Gly (29).…”

Section: Methodsmentioning

confidence: 99%

Neurohypophyseal hormones, analogs, and fragments: their effect on puromycin-induced amnesia.

Walter¹,

Hoffman²,

Flexner³

et al. 1975

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

100

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Neurohypophyseal hormones and several of their analogs as well as N-terminal and C-terminal fragments, have been studied for their ability to attenuate puromycin-induced amnesia in mice. arginine]vasopressin, and the analogs des--0lycinamide{8-lysine]vasopressin, [1-p-mercaptopropionic acid, 8-lysinelvasopressin, [1,6-aminosuberic acid, 8-lysine vasopressin, [4-leu- Gly-NH2, as well as its derivatives D-Leu-Gly-NH2 and the diketopiperazine, cyclo(-Leu-Gly-).Peptides possessing behavioral and electrophysiological activities are the focus of increasing attention (1-9). Among these peptides are the antidiuretic hormone of pig, [8-ly-sine]vasopressin (LVP) (for primary structures see Fig. 1), and des-9-glycinamide-LVP (DGLVP), which was isolated from hog pituitary (6). The peptides delay extinction of active avoidance behavior in intact rats (10)(11)(12) and restore the ability of hypophysectomized rats to acquire a conditioned avoidance response (3,5

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Section: Methodsmentioning

confidence: 99%

Neurohypophyseal hormones, analogs, and fragments: their effect on puromycin-induced amnesia.

Walter¹,

Hoffman²,

Flexner³

et al. 1975

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

100

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“…On the other hand, solvent effects could play an important role in the stabilization of preferred conformations because of the possibility of interaction between the hydroxyl group of the N terminus and the solvent [32].…”

Section: Glycine-2 and Glycine-3mentioning

confidence: 99%

270‐MHz ¹H Nuclear‐Magnetic‐Resonance Study of Met‐enkephalin in Water

Zetta

Cabassi

Tomatis

et al. 1979

European Journal of Biochemistry

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'H spectra at 270 MHz of the Met-enkephalin pentapeptide (Tyr-Gly-Gly-Phe-Met) in aqueous solution, as a function of pH and of temperature, are reported.The analysis of the chemical shifts, line widths, coupling constants and rotamer populations around x1 and x2, suggests the existence of three conformational regions in the pH range 1-10, due to some rearrangements of the first two amino acids, Tyr-1 and Gly-2. A first conformational transition occurs corresponding to the N-terminus titration, with an exchange rate between conformational states which is not too fast. The second transition occurs concomitantly with the phenolic group titration. The conformational states of the cationic and zwitterionic forms are probably very similar and are characterized by thc abscncc of intramolccular hydrogcn bonds and of head-to-tail intcractions. A bent structure, with the Tyr-1 ring facing the Gly-2 could contribute to the equilibrium of the conformational states of Met-enkephalin in the pH range 8 -10. This structure could be destabilized as a consequence of the phenolic group deprotonation.The Met-5 and Phe-4 residues appear to have little sensitivity to the conformational transitions of the backbone and both show a settling of the side chains corresponding to the carboxyl group titration, thus showing a reciprocal steric hindrance.The temperature coefficients of the chemical shifts of amide protons at acidic pH are in the range of solvated peptides. In the temperature range 0 -75 "C, the 3 J ,~~ coupling constants were independent of temperature.Met-enkephalin (Tyr-Gly-Gly-Phe-Met), an endogenous pentapeptide that acts on opiate receptors, has recently been the subject of several papers, both experimental and theoretical, aimed at establishing the relationship between structure and activity. Its possible conformations were studied by optical spectroscopy [l], X-ray of related fragments [2], semiempirical conformational calculations [3 -61 and NMR spectroscopy [7-121, 13C and 'H relaxation measurements, both in (C2H3)2S0 and in 2H20 [7, lo], exclude a random-coil structure and agree in showing a rigid backbone, with possible rotational freedom of the Met-5 and Phe-4 side chains and a higher degree of hindrance for the Tyr-1 side chain. Recent proton magnetic resonance measurements in water, (C2H3)2S0 and a mixture of these two [13-151, have apparently In fact, because of its high polarity, water might destabilize intramolecular H bonds and cause unfolded structures with amides exposed to the solvent, while (C2H3)2S0 might protect the intramolecular H bonds and then the folded structures.In order to contribute to the clarification of these results, we have undertaken a systematic study of the spectral characteristics of Met-enkephalin as a function of pH and of temperature in water, this being the most suitable solvent for the reproduction of the physiological environment. Even though the study of Met-enkephalin in other solvents gives information on the stability of the energetically possible conformational states, from...

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“…It suggests that the shielding of one ring by the other influences mainly these positions of the arom atic ring. It is known that the absolute magnitude of the ring-current effect is the same for 13C as for 'H nucleus, if they occupy the same posi tions in space relative to the arom atic 7r-electron cloud [17,18], The effects observed by us in 13C and 'H N M R spectra are really comparable in their magnitudes.…”

Section: Resultsmentioning

confidence: 93%

A New Example of Edge-to-Face Interaction of Aromatic Rings in Oligopeptides: Cyclolinopeptide A

Siemion¹

1990

Zeitschrift Für Naturforschung B

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The analysis of the aromatic region of 1H and 13C NMR spectra of cyclolinopeptide A (cyclic nonapeptide with the sequence c—(Pro— Pro— Phe—Phe—Leu— Ile— Ile— Leu— Val— ), (CLA)) shows that Phe-3 and Phe-4 aromatic rings are oriented nearly perpendicularly to each other, forming edge-to-face pair. It signifies the strong limitation of the free rotation of aromatic residues, probably because of the steric hindrance exerted by proximal aliphatic side chains of CLA.

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Carbon-13 nuclear magnetic resonance studies of the conformations of cyclic dipeptides

Cited by 76 publications

References 11 publications

Neurohypophyseal hormones, analogs, and fragments: their effect on puromycin-induced amnesia.

Neurohypophyseal hormones, analogs, and fragments: their effect on puromycin-induced amnesia.

270‐MHz ¹H Nuclear‐Magnetic‐Resonance Study of Met‐enkephalin in Water

A New Example of Edge-to-Face Interaction of Aromatic Rings in Oligopeptides: Cyclolinopeptide A

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Carbon-13 nuclear magnetic resonance studies of the conformations of cyclic dipeptides

Cited by 76 publications

References 11 publications

Neurohypophyseal hormones, analogs, and fragments: their effect on puromycin-induced amnesia.

Neurohypophyseal hormones, analogs, and fragments: their effect on puromycin-induced amnesia.

270‐MHz 1H Nuclear‐Magnetic‐Resonance Study of Met‐enkephalin in Water

A New Example of Edge-to-Face Interaction of Aromatic Rings in Oligopeptides: Cyclolinopeptide A

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270‐MHz ¹H Nuclear‐Magnetic‐Resonance Study of Met‐enkephalin in Water