Currently, there is a lot of interest in bolaamphiphiles because of the unusual architecture created by such molecules as they possess not one but two hydrophilic heads, coupled by a hydrophobic linker. Only a limited amount of bolaamhiphiles can be produced microbially. Applying a combination of white biotechnology and green chemistry can dramatically increase the structural possibilities starting from sustainable building blocks, such as microbially produced sophorolipids. The resulting molecular libraries can subsequently be screened for interesting properties (what will be the major objective of the AppliSurf project). In this article, the application of these innovative bolaamphiphilic compounds in the medical sector is investigated. More specific, the antimicrobial activity, transfection efficiencies and self-assembly properties of bolaamphiphilic molecules were evaluated.