Chemical synthesis of C-C-bond formations is difficult, unselective and requires often increased financial and time-effort. Therefore, enzymatic attended syntheses of C-C coupling in non-aromatic and aromatic systems. Chapter 1 presents an overview of prenylated compounds and introduces the enzyme family PTases and aromatic PTase. Chapter 2 focuses on linear prenylation to form UPP using alternative IPP-substrates for prolongation. Chapter 3 describes NphB and questions the substrate bindings in the enzyme and the catalytic cascade. Chapter 4 shows the application of the NphB-products. Chapter 5 describes the development of an UV/Vis procedure to quantify the formation of geranylated 1,6-DHN and the stabling of the quantitative NMR. Chapter 6 focuses on the inhibition of aromatic prenyltransferases with prenyl diphosphate mimeticas using the enzyme NphB, MenA and UbiA. Chapter 7 summaries the methods used in this thesis.