Chemoenzymatic synthesis of optically active, biodegradable polymers based on phenyl- and naphthyl-ethanols esterified with divinyladipate.
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.
Raku
Takao
T
National Institute of Advanced Industrial Science and Technology, Tsukuba Central 6, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8566, Japan.
Tokiwa
Yutaka
Y
D000272:Adipates / Q000737:chemistry / Q000378:metabolism*; D001592:Benzyl Alcohols / Q000378:metabolism; D004951:Esterification; D004952:Esters / Q000737:chemistry; D000431:Ethanol / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism; D008049:Lipase / Q000378:metabolism*; D009281:Naphthalenes / Q000378:metabolism; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000378:metabolism; D011108:Polymers / Q000737:chemistry / Q000378:metabolism*; D011549:Pseudomonas / Q000201:enzymology; D013237:Stereoisomerism
D000272:Adipates; D001592:Benzyl Alcohols; D004952:Esters; D009281:Naphthalenes; D011108:Polymers; C007476:1,1-dimethylphenylethanol; C403616:1-(2-naphthyl)ethanol; D000431:Ethanol; C472390:divinyl adipate; C002017:methylphenyl carbinol; D008049:Lipase; D010626:Phenylethyl Alcohol