Direct enzymatic synthesis of a polyester with free pendant mercapto groups.
An aliphatic polyester with free pendant mercapto groups was prepared by direct lipase-catalyzed polycondensation of hexane-1,6-diol and dimethyl 2-mercaptosuccinate. The polycondensation reaction using immobilized lipase from Candida antarctica (lipase CA) was carried out in bulk at 70 degrees C without any formation of disulfide or thioester linkages to produce the corresponding polyester with Mw = 14000 g/mol in high yield. The content of free mercapto groups in the polyester could be controlled by copolymerization with other monomers. The obtained polyester was easily cross-linked to form gels by the air oxidation of the pendant thiols to disulfides in dimethyl sulfoxide.
Kato
Makoto
M
Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. dr064519@yahoo.co.jp
Toshima
Kazunobu
K
Matsumura
Shuichi
S
D002175:Candida / Q000201:enzymology; D004800:Enzymes, Immobilized / Q000378:metabolism; D005782:Gels; D008049:Lipase / Q000378:metabolism*; D011091:Polyesters / Q000138:chemical synthesis*; D013438:Sulfhydryl Compounds
D004800:Enzymes, Immobilized; D005782:Gels; D011091:Polyesters; D013438:Sulfhydryl Compounds; D008049:Lipase