In order to understand the relationship between the durability of adhesive strength in the oral cavity and water absorption, a series of O-methacryloyl-N-acyl tyrosines (MAATY)-2-hydroxyethyl methacrylate (HEMA) bond system samples was prepared and their bonding strength to unetched human dentin was measured as a function of immersion period in water. Also, bulk polymerization was carried out to measure the amount of water absorption as a function of time. All specimens absorbed water suddenly when they were immersed into water. The amount of absorbed water was large when the carbon number in the acyl group was small or the number of carboxylic groups was large. The adhesive strength of the MAATY-HEMA system to unetched dentin decreased significantly when the MAATY-HEMA absorbed a larger amount of water. We concluded, therefore, that preparation of MAATY which absorbs less water may improve durability even when immersed in water.