Regio- and stereo-selective synthesis of vinyl glucose ester catalyzed by an alkaline protease of Bacillus subtilis |
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Authors: | Qi Wu Deshui Lu Ying Cai Xingtao Xue Zhichun Chen Xianfu Lin |
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Affiliation: | (1) Department of Chemistry, Zhejiang University, Hangzhou, 310027, People's Republic of China |
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Abstract: | The transesterification of -d-glucose with divinylsuccinate, divinyladipate and divinylsebacate in pyridine at 55 °C for 3 days was catalyzed by an alkaline protease from Bacillus subtilis to give corresponding 6-O-vinyl glucose esters at 30%, 53% and 35% yield, respectively. The stereo-selectivity of the alkaline protease toward the -anomer was affected by the acyl donor chain length. 6-O-Vinylsuccinyl-d-glucose was mixture of - and -anomers (/=44/56), the other two products were the pure -d-glucose derivatives. |
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Keywords: | alkaline protease Bacillus subtilis regioselectivity stereoselectivity vinyl glucose ester |
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