A facile method for preparation of polymerizable, optically active ketoprofen prodrug by irreversible lipase-catalysed resolution

作者：Cai XQ; Chen ZC; Wang N; Lin XF^*

来源：WORLD JOURNAL OF MICROBIOLOGY & BIOTECHNOLOGY, 2006, 22(7): 723-727.

DOI：10.1007/s11274-005-9096-y

• enantioselectivity
• irreversible resolution
• ketoprofen
• lipases
• prodrug
• vinyl esters

An irreversible resolution of ketoprofen prodrug was developed by lipase-catalysed hydrolysis using corresponding vinyl ester as activated substrate in organic medium. The product obtained, (S)-ketoprofen vinyl ester would be used as a potential prodrug and a significant monomer for polymeric drug. Lipozyme (R) immobilized from Mucor miehei showed the highest selectivity and activity after enzyme screening. The effect of solvent, water amount in the reaction medium and reaction temperature on the activity and enantioselectivity of Lipozyme (R) was studied. Polymerizable, optically active ketoprofen prodrug could be obtained with excellent enantioselectivity (ee > 99%, E similar to 400) in a mixture of dioxane/water (97.5/2.5, v/v) at 25 degrees C.

• 出版日期2006-7
• 单位浙江大学