Synthesis of Non-Natural Aromatic Amino Acids Derivatives Solvent-free reactions-Versatile building blocks-Galectin inhibitors

University dissertation from Organic Chemistry, Center for Chemistry and Chemical Engineering, Lund University

Abstract: This thesis deals with three topics concerning the synthesis of non-natural also known as unnatural amino acid derivatives. In the first, solvent-free reaction conditions for the Heck reaction were developed that were superior to previous conditions because the reaction time could be reduced and the work-up procedure simplified. Appropriately substituted, unnatural amino acid derivatives, synthesized by this method, cyclised to form indoles. In the second, versatile aldehyde building blocks were synthesised that could be functionalised selectively in a stepwise fashion for the synthesis of multifunctional branched unnatural amino acids. In the third, multivalent carbohydrate derivatives of unnatural amino acids were prepared as inhibitors of tumor- and inflammation-related galectins and were found to be selective against galectin-1.

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