To control degradation rate of biodegradable poly(lactide)s (PLA), the stereochemical PLAs with different ratios of d-lactide and l-lactide units were synthesized by the ring open polymerization and the their degradation kinetics were measured by a Langmuir film balance. The alkaline (pH=11) degradation of poly(l-lactide) (l-PLA) monolayer showed the faster rate at a surface pressure of 4 mN/m in the ranges from to 0 to 7 mN/m. However, the enzymatic degradation of l-PLA with Proteinase K did not occur until 4 mN/m. Above a constant surface pressure of 4 mN/m, the degradation rate was increased with a constant surface pressure. These behaviors might be attributed to the difference in the contacted area with degradation medium: alkaline ions need small contact area with l-PLA while enzymes require much bigger one to be activated due to different medium sizes. The stereochmical PLA monolayers showed that the alkaline degradation was increased with their optical impurities while the enzymatic one was inversed. These results could be explained by the decrease of crystallinity with the optical impurity and the inactivity of enzyme to d-LA unit.