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Chemoenzymatic synthesis of optically active, biodegradable polymers based on phenyl- and naphthyl-ethanols esterified with divinyladipate.
- Source :
-
Biotechnology letters [Biotechnol Lett] 2004 Apr; Vol. 26 (8), pp. 665-70. - Publication Year :
- 2004
-
Abstract
- For the purpose of developing a new synthetic polymer containing an asymmetric molecule branch, three racemic alcohols, i.e. 1-phenylethanol, 1-(4-methylphenyl)ethanol and 1-(2-naphthyl)ethanol, were esterified enzymatically with divinyladipate using a lipase from Pseudomonas cepacia. The enzymatic acylation of alcohols produced monoacylated products. Optically active polymerizable monomers, (R)-vinyl adipic acid (phenyl-1-yl) ethyl ester, (R)-vinyl adipic acid (4-methylphenyl-1-yl) ethyl ester and (R)-vinyl adipic acid (2-naphthyl-1-yl) ethyl ester with enantiometric excesses over 99%, 96% and 99%, respectively, were obtained. Each optically active monomer was then subjected to free radical polymerization, to give polymers having a number average molecular weight of 2.9 x 10(3) - 2.2 x 10(4). These polymers are considered useful as optically active polymers having biodegradability.
- Subjects :
- Adipates chemistry
Benzyl Alcohols metabolism
Esterification
Esters chemistry
Ethanol metabolism
Naphthalenes metabolism
Phenylethyl Alcohol metabolism
Polymers chemistry
Pseudomonas enzymology
Stereoisomerism
Adipates metabolism
Ethanol analogs & derivatives
Ethanol chemistry
Lipase metabolism
Phenylethyl Alcohol analogs & derivatives
Polymers metabolism
Subjects
Details
- Language :
- English
- ISSN :
- 0141-5492
- Volume :
- 26
- Issue :
- 8
- Database :
- MEDLINE
- Journal :
- Biotechnology letters
- Publication Type :
- Academic Journal
- Accession number :
- 15200178
- Full Text :
- https://doi.org/10.1023/b:bile.0000023027.84347.e2