Studies of some bioactive N‐p‐methacrylamidobenzoic esters

Abstract

Preparations of four typical bioactive esters of N‐p‐methacrylamidobenzoic monomers and their reactive polymers as immobilized trypsin carriers are described. N‐p‐methacrylamidobenzoic active ester monomers containing COONB, COOSu, COOObt, or COOBT group can react with an aliphatic amine such as benzylamine at room temperature to give an identical product, N‐benzyl‐p‐methacrylamidobenzamide. However, only monomers with COOObt or COOBT group can also react with an aromatic amine such as aniline to give N‐phenyl‐p‐methacrylamidobenzamide. These monmoers polymerized readily in solution with azobisisobutyronitrile as free‐radical initiator; the polymers were used to immobilize trypsin. Among the four different active esters for the immobilization of trypsin, thE HONB and HOSu active ester showed rather higher bioactivities than the HOObt or HOBT active ester under the same conditions. Both P(MABONB)‐trypsin and P(MABOSu)‐trypsin matrices possess higher biological activities by about four or three times that of P(MABOObt)‐trypsin or P(MABOBT)‐trypsin matrices, respectively. It is proposed that these rather high bioactivities may be attributed to the “specific” aminolysis of reactive polymer with COONB or COOSu active ester group by aliphatic amino substituents.