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Synthesis and Characterisation of Natural Phosphodiesters, and Analogues, from Animals

Partridge, Lynda Zoë; (1990) Synthesis and Characterisation of Natural Phosphodiesters, and Analogues, from Animals. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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Several unusual guanidinated and non-guanidinated alkoxyphosphophoryl- ethanolamine derivatives have been found in various groups of lower animals. The guanidinated forms are thought to act as intracellular regulators of high energy phosphate compounds in a similar way to creatine and arginine. Lombricine (2-amino-2-carboxyethyl 2-guanidinoethyl hydrogen phosphate) and its biochemical precursor D-serine ethanolamine phosphodiester contain the unusual D-serine as the alkoxy moiety. This thesis describes:- 1. The development of a novel, general method of synthesising alkoxy and aryloxyphosphorylethanolamine compounds and their guanidinated derivatives using 1,3,2 oxazaphospholidin-2-anes as 'phosphoryl- ethanolamine synthons,' and their structural confirmation by one and two-dimensional nuclear magnetic resonance spectroscopy. 2. The development of high-performance liquid chromatographic (HPLC) analyses on reversed phase columns based on the o- phthaldialdehyde (OPA)-thiol reaction and pre-column derivatisation methodology:- a) To show the presence and concentration of lombricine and N- phosphoryl lombricine in crude worm tissue extracts. b) Using diastereoisomer formation by the OPA-chiral thiol derivatisation, to establish the enantiomeric configuration of the serine moiety in lombricine samples from several different animals, thereby proving that the natural lombricine from earthworms contains the D-seryl enantiomer. 3. The extension of the latter technique to the resolution of the enantiomers of the neuroexcitatory, non-protein 2-amino-Q- phosphonoalkanoic acid homologues and ?-methyl-aniinoalanine by reversed-phase HPLC. 4a) The design and synthesis of a homologous series of new, enantiomerically pure N-acyl L-cysteines for use in the formation of diastereoisomers in the OPA-chiral thiol pre-column derivatisation of various amino compounds, b) The study of the chromatographic behavior and resolution of the diastereoisomers formed from the enantiomers of glutamic acid, lombricine and the 2-amino-a)-phosphonoalkanoic acids, by HPLC, using pre-column derivatisation with the new N-acyl L-cysteines and OPA. The advantages of these OPA amino-thiol adducts over those currently used, including reduced retention times, enhanced resolution and improved fluorescent properties, mean that they could prove valuable in recognising the minor enantiomeric impurities in drugs and food additives based on optically active primary amines.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Synthesis and Characterisation of Natural Phosphodiesters, and Analogues, from Animals
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest.
URI: https://discovery.ucl.ac.uk/id/eprint/10122693
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