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Theses

β-PEPTIDES CYCLOBUTANIQUES

Abstract : The synthesis of β-amino acids, structural analogues of?-Amino acids, is an issue essential in the development of oligopeptides. A lot of work has been conducted on the behavior of β-peptide (sequence of β-amino acids) as well as peptides mixed (mixed β-and β- amino acids). As a result, the conformational preference of β-amino acids will induce the appearance of a three-dimensional structure of the oligopeptide ordered. Thus, several types of helices, sheets and elbows were observed in β-oligopeptides. In addition to this fascinating feature, the β-peptides and peptides showed mixed high stability vis-à-vis digestive enzymes. These characteristics are important in the development of new drug mimics protein structures. In the laboratory, we work on the β-amino acid cyclobutane as a building block of molecular structures developed with β-peptides. The bibliographical section, divided into two parts, describes the synthesis deβ-amino acids carbocyclic then the different types of secondary structures of peptides derived from β-amino acid compounds. Work has been conducted on the β-amino acid cyclic 6, 5 and 4-membered ring. However, no work has been described on the trans-cyclobutane β-amino acid "trans-ACBC." We have undertaken to access the cis-and trans-ACBC optically enriched and we put developed two synthetic routes multigram scale. The key step common to both synthesis and photocycloaddition the [2 +2] of ethylene and a partner to create enone cyclobutane. Using peptide coupling methods, we prepared the dimer, tetramer, and hexamer octamer of 1R, 2R-trans-ACBC. Through several characterization techniques commonly used in the study conformational polypeptides, we were able to determine with certainty the existence of a helix- 12 from the hexamer. In parallel, we conducted a comprehensive study of molecular modeling led us to the same result. This work on the synthesis of optically pure ACBC and the behavior of β-peptides cyclobutaniques completes the picture of carbocyclic β-peptides. We plan to prepare β-amino acids cyclobutaniques functionalized, in order to build-β peptides structured for application in medicinal chemistry.
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Submitted on : Tuesday, September 11, 2012 - 4:53:21 PM
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  • HAL Id : tel-00731023, version 1

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Carlos Fernandez. β-PEPTIDES CYCLOBUTANIQUES. Chimie organique. Université Blaise Pascal - Clermont-Ferrand II, 2008. Français. ⟨NNT : 2008CLF21870⟩. ⟨tel-00731023⟩

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