Loughborough University
Browse
Thesis-2009-Seager.pdf (2.87 MB)

Cycloaddition routes to pyrazole and pyrazoline amino acids

Download (2.87 MB)
thesis
posted on 2018-09-12, 10:01 authored by Laura E. Seager
In recent years, the design and synthesis of structures that can potentially mimic the properties of the peptide bond have been of great interest to biological chemists. We are investigating the synthesis of novel pyrazoline-based structures as potential peptide mimetics. The pyrazoline unit is assembled by 1,3-dipolar cycloaddition of nitrile imines, which are generated in situ from hydrazonyl chlorides. We have investigated two routes to afford the hydrazonyl chloride, (1) via a hydrazone and (2) via a hydrazide, both of which have resulted in the successful synthesis of the desired pyrazolines. Subsequent syntheses have been carried out using a variety of different dipoles and dipolarophiles. We have taken approach (1) and used this to synthesize a pyrazole as one major enantiomer. [Illustration omitted.] This pyrazole has been subject to peptide couplings to form a complete peptide mimetic. [Illustration omitted.] NMR studies have been carried out on the synthesized peptide mimetic to determine the degree of hydrogen bonding and β-turn characteristics.

History

School

  • Science

Department

  • Chemistry

Publisher

© Laura E. Seager

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2009

Notes

A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.

Language

  • en

Usage metrics

    Chemistry Theses

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC