New Methods in Peptide Synthesis

Gazis, Euthymios.; Borovas, Dimitrios.; Hamalidis, Charalambos; Stelakatos, G. C.; Zervas, Leonidas

doi:10.1016/b978-1-4831-9851-4.50021-8

Peptides 1966

DOI: 10.1016/b978-1-4831-9851-4.50021-8

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New Methods in Peptide Synthesis

Euthymios. Gazis

Dimitrios. Borovas

Charalambos Hamalidis

et al.

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1991

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“…[Cpp', Sar'IAVP is a selective pressor antagonist ( P A , = 7.93; ref. 21), though not as potent as [Cpp'IAVP ( p A 2 = 8. 35; ref.…”

mentioning

confidence: 87%

Conformational analysis of [Cpp¹, Sar⁷, Arg⁸] vasopressin by ¹H‐NMR spectroscopy and molecular mechanics calculations

Shenderovich

Kasprzykowski

Liwo

et al. 1991

International Journal of Peptide and Protein Research

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A combined 'H-NMR and molecular mechanics study of [Cpp', Sar7]AVP was performed in order to select the most probable conformations in DMSO solutions. The NMR constraints obtained were employed in the selection of starting conformations of the cyclic moiety of the analog. In particular, the diminished accessibility of the Asn' NH proton to solvent and the close contact between Cpp' and Cys6 C'H protons suggests a 8-turn conformation at the Phe'-Gln4 residues. Energy minimization was carried out both in the ECEPP/2 (rigid-valence geometry) and in the AMBER (flexible-valence geometry) force fields. Comparison of the experimental and calculated values of NMR characteristics has revealed that conformations containing type I, 11, and 111 P-turns at the Phe3-Gln4 residues are in reasonable agreement with the experimental data, with a dynamic equilibrium between the 81 (PIII) and p11 type structures of the cyclic part being the most probable. All of these conformations prefer the negative chirality of the disulfide bridge (xz 2 -90").Five representative conformations were chosen for the acyclic tail: one with a PI, one with a bII'-turn at the Sar7-Arg' residues, two extended-type conformations, and a conformation with a ;-turn at Sar7. Because only high-energy extended conformations were in agreement with NMR data, it was concluded that the acyclic tail has considerable conformational flexibility in solution. The conformations obtained are discussed in terms of the structure-function relationship of the neurohypophyseal hormone analogs.

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“…[Cpp', Sar'IAVP is a selective pressor antagonist ( P A , = 7.93; ref. 21), though not as potent as [Cpp'IAVP ( p A 2 = 8. 35; ref.…”

mentioning

confidence: 87%

Conformational analysis of [Cpp¹, Sar⁷, Arg⁸] vasopressin by ¹H‐NMR spectroscopy and molecular mechanics calculations

Shenderovich

Kasprzykowski

Liwo

et al. 1991

International Journal of Peptide and Protein Research

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show abstract

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New Methods in Peptide Synthesis

Cited by 1 publication

References 6 publications

Conformational analysis of [Cpp¹, Sar⁷, Arg⁸] vasopressin by ¹H‐NMR spectroscopy and molecular mechanics calculations

Conformational analysis of [Cpp¹, Sar⁷, Arg⁸] vasopressin by ¹H‐NMR spectroscopy and molecular mechanics calculations

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New Methods in Peptide Synthesis

Cited by 1 publication

References 6 publications

Conformational analysis of [Cpp1, Sar7, Arg8] vasopressin by 1H‐NMR spectroscopy and molecular mechanics calculations

Conformational analysis of [Cpp1, Sar7, Arg8] vasopressin by 1H‐NMR spectroscopy and molecular mechanics calculations

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Conformational analysis of [Cpp¹, Sar⁷, Arg⁸] vasopressin by ¹H‐NMR spectroscopy and molecular mechanics calculations

Conformational analysis of [Cpp¹, Sar⁷, Arg⁸] vasopressin by ¹H‐NMR spectroscopy and molecular mechanics calculations