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.

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: https://theses.gla.ac.uk/id/eprint/77165