Bioconversion of N-Butylglucamine to 6-Deoxy-6-butylamino Sorbose by Gluconobacter oxydans
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- 作者：Bryan H. Landis ; Joseph K. McLaughlin ; Robert Heeren ; Roy W. Grabner ; and Ping T. Wang
- 刊名：Organic Process Research & Development
- 出版年：2002
- 出版时间：July 2002
- 年：2002
- 卷：6
- 期：4
- 页码：547 - 552
- 全文大小：68K
- 年卷期：v.6,no.4(July 2002)
- ISSN：1520-586X
文摘
Gluconobacter oxydans has the unique ability to regioselectivelyand rapidly oxidize sorbitol and other erythro saccharides. Inthis report a new process is described by which N-butylglucamine is regioselectively oxidized by the organism. A large-scale process is described by which N-butylglucamine can beconverted to an intermediate (6-deoxy-6-butylaminosorbose)which can be readily converted to N-butyldeoxynojirimycinby catalytic hydrogenation. The primary process variables oftemperature, pH, and added acids and salts were investigatedin laboratory bioreactors. Since degradation of the sorboseproduct was rapid above room temperature, significant enhancement of the selectivity was achieved by lowering thetemperature at which the bioconversion was run. The optimumtemperature for this conversion was 12-15 
C. The pHmaximum of the bioconversion was 5.5-6.0. However, the smallgain in rate relative to pH 5.0 was at least offset by the increasein degradation of the product at the higher pH. Nitrate salts ofN-butylglucamine could replace chloride salts, but sulfate,acetate, and phosphate salts could not. Sulfate in particular ledto inhibition of the conversion, while phosphate and acetate ledto increased degradation. At temperatures in the range of 12-15 C, pH of around 5.0 and substrate concentrations of 0.2M, Gluconobacter oxydans catalyzed bioconversion to 6-deoxy-6-butylaminosorbose with yields approaching 95%. Theseconditions were used to scale this process to 5500-L scale.
C. The pHmaximum of the bioconversion was 5.5-6.0. However, the smallgain in rate relative to pH 5.0 was at least offset by the increasein degradation of the product at the higher pH. Nitrate salts ofN-butylglucamine could replace chloride salts, but sulfate,acetate, and phosphate salts could not. Sulfate in particular ledto inhibition of the conversion, while phosphate and acetate ledto increased degradation. At temperatures in the range of 12-15 C, pH of around 5.0 and substrate concentrations of 0.2M, Gluconobacter oxydans catalyzed bioconversion to 6-deoxy-6-butylaminosorbose with yields approaching 95%. Theseconditions were used to scale this process to 5500-L scale.