Enzymatic ring-opening polymerization was applied to synthesize high molecular weight polypentadecalactone (PPDL). The synthetic procedure was optimized on a small-scale and subsequently transferred to 30 g scale to yield sufficient material for fiber spinning. Molecular weights (Mw) of 143 000 g mol-1 were obtained. Mechanical and thermal properties of the non-oriented, high molecular weight PPDL were determined and are largely in agreement with the literature data. The high molecular weight PPDL was melt-processed into fibers, which were further elongated to about 9–10 times their original length. Analysis of the fibers revealed differences in crystal orientation as a function of the processing conditions. Preliminary fiber tensile measurements confirm a high strength of up to 0.74 GPa for the fiber with the highest crystal orientation.