The synthesis of novel cyclic agelasphin derivatives

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

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Abstract

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
Identifiers:	Number Type PQ10183372 Other
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
URI:	https://irep.ntu.ac.uk/id/eprint/40868

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