Chitosan has received much attention as a material for three-dimensional scaffold fabrication for tissue engineering applications because of its excellent biocompatibility and biodegradability. However, its application is limited by its poor solubility in water. In this study, a maleyl group was conjugated onto chitosan through a simple reaction with maleic anhydride. Incorporation of the maleyl group onto chitosan may enhance its solubility in water. The results showed that incorporation of the maleyl group onto chitosan enhanced chitosan solubility in demineralized water (pH = 7) up to 11 mg/mL. Fourier transform infrared and H-nuclear magnetic resonance spectra showed that the maleyl group was successfully incorporated onto the chitosan chain. These findings demonstrate that a simple reaction of chitosan with maleic anhydride can enhance chitosan solubility in water. Furthermore, the obtained maleylated-chitosan can be potentially applied as a material for tissue engineering.