Synthesis and Biosynthesis of Candipolin, a Metabolite of Penicillium canadense

Langham, Helen (1981) Synthesis and Biosynthesis of Candipolin, a Metabolite of Penicillium canadense. PhD thesis, University of Glasgow.

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Abstract

Candipolin, a mycelial metabolite of the fungus Penicillium canadense, is N-benzoyl-O-(N-benzoyl-L-phenylalanyl)-L-phenylalaninol Its structure was deduced from spectroscopic and degradative studies and confirmed by synthesis. Esterification of N-benzoyl-L-phenyl-alaninol with the imidazolide of N-benzoyl-L-phenylalanine yielded a mixture of candipolin and its epimer, the latter arising by racemisation at the phenylalanine centre. Epi-candipolin crystallised from the mixture more easily than candipolin, making isolation of the desired product rather difficult. Candipolin was obtained free from its epimer by esterification of N-benzoyl-L-phenylalaninol with the imidazolide of N-CBZ-L-phenylalanine, followed by selective removal of the CBZ-group and benzoylation.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Biochemistry, Organic chemistry
Date of Award: 1981
Depositing User: Enlighten Team
Unique ID: glathesis:1981-77165
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 14 Jan 2020 09:17
Last Modified: 14 Jan 2020 09:17
URI: http://theses.gla.ac.uk/id/eprint/77165

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