Catalytic and Biocatalytic Methods for the Efficient Synthesis of Biologically Relevant Non-Proteinogenic Amino Acids

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Non-proteinogenic amino acids are often important constituents of biologically potent natural products. The synthesis of these amino acids is often time-consuming, non-trivial and not sustainable. Thus, the central topic of this work was the formation of unusual amino acid structures by biocatalytic and catalytic methods. For the elucidation of the biosynthetic pathway of Streptomyces-produced muraymycins and related natural products, a ‘biosynthetic tool kit’ was compiled and prepared. This does not only comprehend the completed synthesis of deuterium-labeled compounds, such as (3R)- and (3S)-3-hydroxy-[5-2H]-l-arginine and other potential intermediates with a nucleosidic structure, but it also includes the development of fermentation methodology including the possibility to detect the muraymycin derivatives by LC MS. Furthermore, different synthetic routes with catalytic key steps for the preparation of the non-proteinogenic amino acid enduracididine were investigated.