The synthesis of novel cyclic agelasphin derivatives

Rampling, R.A., 2000. The synthesis of novel cyclic agelasphin derivatives. PhD, Nottingham Trent University.

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The agelasphins, α-galactosylceramides, are a group of natural products which exhibit interesting immunomodulating activity. These have served as leads for structural analogues, which are now in clinical trials as anti-cancer agents. The agelasphins and their derivatives are acyclic compounds consisting of a ceramide bound to a galactose, and have conformational freedom.

The aim of the research described herein was to synthesise conformationally restrained analogues of the agelasphins, using structures based on 3-alkyl-3,4-dihydroxy-5-hydroxymethyl pyrrolidinone. Two synthetic strategies were followed. Extensive attempts to prepare the target pyrrolidinones from acyclic precursors were unsuccessful. Elaboration of pyroglutamate derivatives, however, led to 3-(a-hydroxyalkyl)-3-hydroxy-5-hydroxymethylpyrrolidinones, but no 3,4-dihydroxy analogues were obtained.

Coupling of these to glucose or galactose by a variety of methods lead to agelasphin analogues, which were subjected to biological assay.

Item Type: Thesis
Creators: Rampling, R.A.
Date: 2000
ISBN: 9781369315776
Divisions: Schools > School of Science and Technology
Record created by: Linda Sullivan
Date Added: 22 Sep 2020 09:42
Last Modified: 10 Aug 2023 10:23

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