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Title: Synthesis and biosynthesis of candipolin, a metabolite of Penicillium canadense
Author: Langham, Helen
ISNI:       0000 0001 3604 9058
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 1981
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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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Organic chemistry