6-deoxy-6-butylaminosorbose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-6-butylaminosorbose
• 英文别名: 6-(n-butylamino)-6-deoxy-L-sorbose；(3S,4R,5S)-6-(butylamino)-1,3,4,5-tetrahydroxyhexan-2-one
• 化学式: C₁₀H₂₁NO₅
• 分子量: 235.28
• InChiKey: OELIVZLBOYQGKF-FXBDTBDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-deoxy-6-butylaminosorbose 在 4% Pd/C 、 氢气 作用下， 以 水 为溶剂， 20.0 ℃ 、446.08 kPa 条件下， 反应 2.33h， 生成 米格鲁他
  参考文献：
  名称：

  Bioconversion of N-Butylglucamine to 6-Deoxy-6-butylamino Sorbose by Gluconobacter oxydans

  摘要：

  Gluconobacter oxydans has the unique ability to regioselectively and rapidly oxidize sorbitol and other erythro saccharides. In this 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 be converted to an intermediate (6-deoxy-6-butylaminosorbose) which can be readily converted to N-butyldeoxynojirimycin by catalytic hydrogenation. The primary process variables of temperature, pH, and added acids and salts were investigated in laboratory bioreactors. Since degradation of the sorbose product was rapid above room temperature, significant enhancement of the selectivity was achieved by lowering the temperature at which the bioconversion was run. The optimum temperature for this conversion was 12-15 degreesC. The pH maximum of the bioconversion was 5.5-6.0. However, the small gain in rate relative to pH 5.0 was at least offset by the increase in degradation of the product at the higher pH. Nitrate salts of N-butylglucamine could replace chloride salts, but sulfate, acetate, and phosphate salts could not. Sulfate in particular led to inhibition of the conversion, while phosphate and acetate led to increased degradation. At temperatures in the range of 1215 degreesC, pH of around 5.0 and substrate concentrations of 0.2 M, Gluconobacter oxydans catalyzed bioconversion to 6-deoxy-6-butylaminosorbose with yields approaching 95%. These conditions were used to scale this process to 5500-L scale.

  DOI：

  10.1021/op0255128
• 作为产物：
  描述：

  1-n-butylamino-1-deoxy-D-glucitol 在 Gluconobacter oxydans 作用下， 以 水 为溶剂， 以95%的产率得到6-deoxy-6-butylaminosorbose
  参考文献：
  名称：

  Bioconversion of N-Butylglucamine to 6-Deoxy-6-butylamino Sorbose by Gluconobacter oxydans

  摘要：

  Gluconobacter oxydans has the unique ability to regioselectively and rapidly oxidize sorbitol and other erythro saccharides. In this 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 be converted to an intermediate (6-deoxy-6-butylaminosorbose) which can be readily converted to N-butyldeoxynojirimycin by catalytic hydrogenation. The primary process variables of temperature, pH, and added acids and salts were investigated in laboratory bioreactors. Since degradation of the sorbose product was rapid above room temperature, significant enhancement of the selectivity was achieved by lowering the temperature at which the bioconversion was run. The optimum temperature for this conversion was 12-15 degreesC. The pH maximum of the bioconversion was 5.5-6.0. However, the small gain in rate relative to pH 5.0 was at least offset by the increase in degradation of the product at the higher pH. Nitrate salts of N-butylglucamine could replace chloride salts, but sulfate, acetate, and phosphate salts could not. Sulfate in particular led to inhibition of the conversion, while phosphate and acetate led to increased degradation. At temperatures in the range of 1215 degreesC, pH of around 5.0 and substrate concentrations of 0.2 M, Gluconobacter oxydans catalyzed bioconversion to 6-deoxy-6-butylaminosorbose with yields approaching 95%. These conditions were used to scale this process to 5500-L scale.

  DOI：

  10.1021/op0255128

文献信息

• [EN] PROCESS FOR PREPARATION OF 1,5-(ALKYLIMINO)-1,5-DIDEOXY-D-GLUCITOL AND DERIVATIVES THEREOF
  申请人：G.D. SEARLE & CO.

  公开号：WO1991017145A1

  公开（公告）日：1991-11-14

  (EN) Process for the preparation of 1,5-(alkylimino)-1,5-dideoxy-D-glucitol and derivatives thereof. Described is a process for the preparation of 1,5-(n-butylimino)-1,5-dideoxy-D-glucitol and similar compounds and to the use of an adsorption hydrogenation protocol.(FR) Procédé de préparation de 1,5-(alkylimino)-1,5-didésoxy-D-glucitol et de ses dérivés. L'invention concerne un procédé de préparation de 1,5-(n-butylimino)-1,5-didésoxy-D-glucitol ainsi que de composés similaires, et l'emploi d'un protocole d'hydrogénation par adsorption.

  (中文) 一种制备1,5-(烷基亚胺基)-1,5-二脱氧-D-葡萄糖醇及其衍生物的方法。描述了一种制备1,5-(正丁基亚胺基)-1,5-二脱氧-D-葡萄糖醇及类似化合物的方法，并使用吸附氢化协议。
• US5151519A
  申请人：——

  公开号：US5151519A

  公开（公告）日：1992-09-29
• US5281724A
  申请人：——

  公开号：US5281724A

  公开（公告）日：1994-01-25
• Bioconversion of <i>N</i>-Butylglucamine to 6-Deoxy-6-butylamino Sorbose by <i>Gluconobacter </i><i>o</i><i>xydans</i>
  作者：Bryan H. Landis、Joseph K. McLaughlin、Robert Heeren、Roy W. Grabner、Ping T. Wang

  DOI：10.1021/op0255128

  日期：2002.7.1

  Gluconobacter oxydans has the unique ability to regioselectively and rapidly oxidize sorbitol and other erythro saccharides. In this 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 be converted to an intermediate (6-deoxy-6-butylaminosorbose) which can be readily converted to N-butyldeoxynojirimycin by catalytic hydrogenation. The primary process variables of temperature, pH, and added acids and salts were investigated in laboratory bioreactors. Since degradation of the sorbose product was rapid above room temperature, significant enhancement of the selectivity was achieved by lowering the temperature at which the bioconversion was run. The optimum temperature for this conversion was 12-15 degreesC. The pH maximum of the bioconversion was 5.5-6.0. However, the small gain in rate relative to pH 5.0 was at least offset by the increase in degradation of the product at the higher pH. Nitrate salts of N-butylglucamine could replace chloride salts, but sulfate, acetate, and phosphate salts could not. Sulfate in particular led to inhibition of the conversion, while phosphate and acetate led to increased degradation. At temperatures in the range of 1215 degreesC, pH of around 5.0 and substrate concentrations of 0.2 M, Gluconobacter oxydans catalyzed bioconversion to 6-deoxy-6-butylaminosorbose with yields approaching 95%. These conditions were used to scale this process to 5500-L scale.