3-脱氧-3氟-D-葡萄糖醇 | 34339-82-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 中文名称: 3-脱氧-3氟-D-葡萄糖醇
• 中文别名: 3-脱氧-3-氟-d-葡萄糖醇
• 英文名称: 3-fluoro-D-glucitol
• 英文别名: 3-Desoxy-3-fluor-D-glucitol；3-fluoro-D-3-deoxy-glucitol；3-Deoxy-3-fluoro-D-glucitol；(2R,3R,4R,5S)-4-fluorohexane-1,2,3,5,6-pentol
• CAS: 34339-82-7
• 化学式: C₆H₁₃FO₅
• 分子量: 184.165
• InChiKey: ZEGLBRXQLUKRML-SLPGGIOYSA-N

物化性质

• 沸点：
  501.5±45.0 °C(Predicted)
• 密度：
  1.508±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• 海关编码：
  2905590090

反应信息

• 作为反应物：
  描述：

  3-脱氧-3氟-D-葡萄糖醇 在 DL-dithiothreitol 、 山梨醇脱氢酶(绵羊肝脏) 、 β-烟酰胺腺嘌呤二核苷酸 作用下， 以 水 为溶剂， 生成 3-deoxy-3-fluoro-D-fructose
  参考文献：
  名称：

  The use of fluoro- and deoxy-substrate analogs to examine binding specificity and catalysis in the enzymes of the sorbitol pathway

  摘要：

  The carbohydrate specificity of the two enzymes that catalyze the metabolic interconversions in the sorbitol pathway, aldose reductase and sorbitol dehydrogenase, has been examined through the use of fluoro- and deoxy-substrate analogs. Hydrogen bonding has been shown to be the primary mode of interaction by which these enzymes specifically recognize and bind their respective polyol substrates. Aldose reductase has broad substrate specificity, and all of the fluoro- and deoxysugars that were examined are substrates for this enzyme. Unexpectedly, both 3-fluoro- and 4-fluoro-D-glucose were found to be better substrates, with significantly lower K-m and higher k(cat)/K-m values than those of D-glucose. A more discriminating pattern of substrate specificity is observed for sorbitol dehydrogenase. Neither the 2-fluoro nor the 2-deoxy analogs of D-glucitol were found to be substrates or inhibitors, suggesting that the 2-hydroxyl group of sorbitol is a hydrogen bond donor. The 4-fluoro and 4-deoxy analogs are poorer substrates than sorbitol, also implying a binding role for this hydroxyl group. In contrast, both 6-fluoro- and 6-deoxy-D-glucitol are very good substrates for sorbitol dehydrogenase, indicating that the primary hydroxyl group at this position is not involved in substrate recognition by this enzyme. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00266-3
• 作为产物：
  描述：

  (3S,4S,5R,6R)-4-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,5-triol 在 aldose reductase 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 水 为溶剂， 生成 3-脱氧-3氟-D-葡萄糖醇
  参考文献：
  名称：

  The use of fluoro- and deoxy-substrate analogs to examine binding specificity and catalysis in the enzymes of the sorbitol pathway

  摘要：

  The carbohydrate specificity of the two enzymes that catalyze the metabolic interconversions in the sorbitol pathway, aldose reductase and sorbitol dehydrogenase, has been examined through the use of fluoro- and deoxy-substrate analogs. Hydrogen bonding has been shown to be the primary mode of interaction by which these enzymes specifically recognize and bind their respective polyol substrates. Aldose reductase has broad substrate specificity, and all of the fluoro- and deoxysugars that were examined are substrates for this enzyme. Unexpectedly, both 3-fluoro- and 4-fluoro-D-glucose were found to be better substrates, with significantly lower K-m and higher k(cat)/K-m values than those of D-glucose. A more discriminating pattern of substrate specificity is observed for sorbitol dehydrogenase. Neither the 2-fluoro nor the 2-deoxy analogs of D-glucitol were found to be substrates or inhibitors, suggesting that the 2-hydroxyl group of sorbitol is a hydrogen bond donor. The 4-fluoro and 4-deoxy analogs are poorer substrates than sorbitol, also implying a binding role for this hydroxyl group. In contrast, both 6-fluoro- and 6-deoxy-D-glucitol are very good substrates for sorbitol dehydrogenase, indicating that the primary hydroxyl group at this position is not involved in substrate recognition by this enzyme. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00266-3

文献信息

• INTRINSIC INHIBITORS OF ALDOSE REDUCTASE
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA as represented by the SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP0686164B1

  公开（公告）日：1998-12-30
• SYSTEMS AND METHODS FOR EVALUATING ENZYME COMPETENCY
  申请人：University of Florida Research Foundation, Inc.

  公开号：EP1805323B1

  公开（公告）日：2010-02-24
• US5560936A
  申请人：——

  公开号：US5560936A

  公开（公告）日：1996-10-01
• US5738878A
  申请人：——

  公开号：US5738878A

  公开（公告）日：1998-04-14
• US5928670A
  申请人：——

  公开号：US5928670A

  公开（公告）日：1999-07-27