2-fluoro-D-glucitol | 34339-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-fluoro-D-glucitol
• 英文别名: 2-deoxy-2-fluoro-D-sorbitol；2-Deoxy-2-fluor-D-glucitol；2-Desoxy-2-fluor-D-glucitol；2-fluoro-D-2-deoxy-glucitol；(2R,3R,4S,5S)-5-fluorohexane-1,2,3,4,6-pentol
• CAS: 34339-80-5
• 化学式: C₆H₁₃FO₅
• 分子量: 184.165
• InChiKey: FHMVCKHFSUAUMP-SLPGGIOYSA-N

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

反应信息

• 作为产物：
  描述：

  2-fluoro-D-glucose 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 生成 2-fluoro-D-glucitol
  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

• [EN] KETAL ESTERS OF ANHYDROPENTITOLS AND USES THEREOF<br/>[FR] CÉTO-ESTERS D'ANHYDROPENTITOLS ET LEURS UTILISATIONS
  申请人：XLTERRA INC

  公开号：WO2010138842A1

  公开（公告）日：2010-12-02

  The present disclosure relates to the preparation of ketal compounds from anhydropentitols and oxocarboxylates; derivatives, homopolymers, and copolymers thereof; and various compositions, formulations, and articles derived therefrom.

  本公开涉及从无水戊糖醇和羰基羧酸酯制备缩酮化合物；以及它们的衍生物、同聚物和共聚物；以及由此衍生的各种组合物、配方和制品。
• [EN] ONE-STEP KIT-BASED SYNTHESIS OF 2-DEOXY-2-[18F]FLUORO-D-SORBITOL<br/>[FR] SYNTHÈSE DE 2-DÉSOXY-2-[18F]FLUORO-D-SORBITOL BASÉE SUR UN KIT EN UNE ÉTAPE
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2022047202A1

  公开（公告）日：2022-03-03

  A self-contained kit and method for the on-demand synthesis of 2-deoxy-2-[18F]fluoro-D-sorbitol (18F-FDS) from commercially available 2-deoxy-2-[18F]fluoroglucose (18F-FDG) is disclosed.

  本发明揭示了一种自包含套件和方法，用于从商业上可获得的2-脱氧-2-[18F]氟葡萄糖（18F-FDG）中按需合成2-脱氧-2-[18F]氟-D-山梨醇（18F-FDS）。
• KETAL ESTERS OF ANHYDROPENTITOLS AND USES THEREOF
  申请人：Selifonov Sergey

  公开号：US20120136070A1

  公开（公告）日：2012-05-31

  The present disclosure relates to the preparation of ketal compounds from anhydropentitols and oxocarboxylates; derivatives, homopolymers, and copolymers thereof; and various compositions, formulations, and articles derived therefrom.
• The use of fluoro- and deoxy-substrate analogs to examine binding specificity and catalysis in the enzymes of the sorbitol pathway
  作者：Mary Ellen Scott、Ronald E. Viola

  DOI：10.1016/s0008-6215(98)00266-3

  日期：1998.12

  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.