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Enzymatic synthesis of a sucrose-containing linear polyester in nearly anhydrous organic media

✍ Scribed by Damodar R. Patil; David G. Rethwisch; Jonathan S. Dordick


Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
710 KB
Volume
37
Category
Article
ISSN
0006-3592

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✦ Synopsis


A variety of enzymes have been found to acylate sucrose in anhydrous pyridine. The enzymic reaction is highly selective; with trifluoroethylbutyrate as ester donor, enzymecatalyzed transesterification of sucrose yielded sucrose 1'-butyrate and sucrose 6,l'-dibutyrate. No sucrose-tributyrates were formed. Using a similar technique, a longchain linear sucrose polyester has been prepared using Proleather, an alkaline protease from a Baci//us sp. This protease catalyzes the esterification of sucrose with bis(2,2,2-trifluoroethyladipate) in a 1 : 1 ratio to yield a sucrose-containing polyester with M, = 2100 and M, = 1600 for a polydispersity of 1.31. Polymers with molecular weights in excess of 13,000 have been prepared by this enzymic approach, indicating that molecules containing over 30 sucrose units have been produced. The polyester is extremely water soluble and soluble in polar organic solvents. As with the sucrose dibutyrate, the polyester has ester linkages at the C6 and C1' positions on the sucrose. The polyester can be depolymerized using Proleather in aqueous buffer, pH1 After 9 days in aqueous buffer, Proleather catalyzed the breakdown of the polyester to an M, of ca. 900. This sucrose-containing polyester may have applications as a water-absorbent, biodegradable plastic for use as diapers and hygienic products, water-treatment chemicals, and components of drug delivery systems.


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