Theoretical conformational analysis of opiate peptides Leu-Enkephalin (H-Tyr-Gly-Gly-Phe-Leu-OH) and its two thioamide analogs (H-Tyr-Glyψ[CSNH]Gly-Phe-Leu-OH) and (H-Tyr-Gly-Glyψ[CSNH]Phe-Leu-OH)

Hassani, Chakib Ameziane; Houssat, Mourad; Hazm, Jamal Eddine

doi:10.1007/s11224-017-1045-5

Cited by 2 publications

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“…conformational studies of several peptide molecules and their structure-activity relationship. 16,[24][25][26][27][28][29][30][31][32] This approach is based on the fact that the structural thermodynamic and statistical properties of a molecular system can be deduced only from a population presenting its conformational space. The principle of PEPSEA consists of generating a population of conformations that characterize a particular peptidic sequence.…”

Section: Introductionmentioning

confidence: 99%

Structural Requirements for Molecular Recognition by fMLP Analogs Receptors: Comparative Conformational Analysis of (for-Met-Leu-Phe-OMe) and its Thioamide Analog (for-Met-Leuψ[CSNH]Phe-OMe)

Hassani

Houssat

Hazm

et al. 2018

ACSi

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In order to determine the structural requirements of fMLP analogs receptors, this work presents the results of a comparative conformational analysis of the active chemotactic peptide (formyl-Met-Leu-Phe-OMe) and its inactive analog (formyl-Met-Leuψ [CSNH] Phe-OMe) using the theoretical method PEPSEA. This study showed that a γ turn structure centered on the central residue is the native structure of the chemotactic peptide fMLP analogs, where both CO(formyl) and NH(central residue) groups are available and ready to interact with the receptor. The inactive analog fML S P-OMe prefers instead a γ turn structure centered on the Met residue, where the two groups cited above are not available for this interaction. Our results and those of literature enable us to propose the "induced fit" model of Burgen for the molecular recognition process. Consequently, the activity of fMLP analogs chemotactic peptides would not be related to a specific secondary structure (β turn, γ turn or extended….) but rather to the freedom and the availability of the CO(formyl) and the NH group at position 2.

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