Structure Elucidation and Biosynthesis of Selected Bioactive Marine Natural Products (Bromophenols, Aplysina, Fistularis, Kelletia)

The biosynthesis of bromophenols in Aplysina fistularis has been reinvestigated, making use of liposome-encapsulated precursors. The incorporation of both phenylalanine and tyrosine into two antimicrobial sponge metabolites, 2,6-dibromo-4-hydroxy-2,5-cyclohexadienone-4-acetamide and 4,6-dibromohomogentisamide, was demonstrated for the first time. Also, {('15)N,('14)C}phenylalanine was shown to be a precursor of the former metabolite, thus providing evidence for the intermediacy of oximes in the conversion of amino acids to other sponge metabolites of biological interest. A biosynthetic pathway consistent with these experiments has been proposed.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Tymiak, Adrienne Anne

• Chemistry, Organic

Identifier

(UMI)AAI8310020

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70214