3-氟-3-脱氧-D-吡喃糖 | 14049-03-7

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-氟-3-脱氧-D-吡喃糖
• 中文别名: 3-氟-3-脱氧-D-葡萄糖
• 英文名称: 3-deoxy-3-fluoro-D-glucose
• 英文别名: 3-fluoro-D-3-deoxy-glucose；(2S,3S,4R,5R)-3-fluoro-2,4,5,6-tetrahydroxyhexanal
• CAS: 14049-03-7
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: RMHCJIQOFXULDL-SLPGGIOYSA-N

物化性质

• 熔点：
  115-117 °C(lit.)
• 溶解度：
  H2O：50 mg/mL，澄清，无色

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT, IRRITANT-HARMFUL
• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  3-氟-3-脱氧-D-吡喃糖 、 乙酸酐 在 吡啶 作用下， 反应 18.0h， 生成 1,2,4,6-tetra-O-acetyl-3-deoxy-3-fluoro-β-D-glucopyranose 、 1,2,4,6-四-o-乙酰基-3-脱氧-3-氟-alpha-d-吡喃葡萄糖
  参考文献：
  名称：

  3-Fluoroazetidinecarboxylic Acids and trans,trans-3,4-Difluoroproline as Peptide Scaffolds: Inhibition of Pancreatic Cancer Cell Growth by a Fluoroazetidine Iminosugar

  摘要：

  Reverse aldol opening tenders amides of 3-hydroxyazetidinecarboxylic acids (3-OH-Aze) unstable above pH 8. Axe, found in sugar beet, is mis-incorporated for proline in peptides in humans and is associated with multiple sclerosis and teratogenesis. Axe-containing peptides may be oxygenated by prolyl hydroxylases resulting in potential damage of the protein by a reverse aldol of the hydroxyazetidine; this, rather than changes in conformation; may account for the deleterious effects of Axe. This paper describes the synthesis of 3-fluoro-Aze amino acids as hydroxy-Aze analogues which are not susceptible to aldol cleavage. 4-(Azidomethyl)-3-fluoro-Aze and 3,4-difluoroproline are new peptide building blocks. trans,trans-2,4-dihydroxy-3-fluoroazetidine, an iminosugar, inhibits the growth of pancreatic cancer cells to a similar degree as gemcitabine.

  DOI：

  10.1021/acs.joc.5b00463
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 在 cesium fluoride 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 44.0h， 生成 3-氟-3-脱氧-D-吡喃糖
  参考文献：
  名称：

  3-Fluoroazetidinecarboxylic Acids and trans,trans-3,4-Difluoroproline as Peptide Scaffolds: Inhibition of Pancreatic Cancer Cell Growth by a Fluoroazetidine Iminosugar

  摘要：

  Reverse aldol opening tenders amides of 3-hydroxyazetidinecarboxylic acids (3-OH-Aze) unstable above pH 8. Axe, found in sugar beet, is mis-incorporated for proline in peptides in humans and is associated with multiple sclerosis and teratogenesis. Axe-containing peptides may be oxygenated by prolyl hydroxylases resulting in potential damage of the protein by a reverse aldol of the hydroxyazetidine; this, rather than changes in conformation; may account for the deleterious effects of Axe. This paper describes the synthesis of 3-fluoro-Aze amino acids as hydroxy-Aze analogues which are not susceptible to aldol cleavage. 4-(Azidomethyl)-3-fluoro-Aze and 3,4-difluoroproline are new peptide building blocks. trans,trans-2,4-dihydroxy-3-fluoroazetidine, an iminosugar, inhibits the growth of pancreatic cancer cells to a similar degree as gemcitabine.

  DOI：

  10.1021/acs.joc.5b00463

文献信息

• [EN] DETECTION OF MYCOBACTERIA<br/>[FR] DÉTECTION DE MYCOBACTÉRIES
  申请人：ISIS INNOVATION

  公开号：WO2011030160A1

  公开（公告）日：2011-03-17

  A method for determining the presence of mycobacteria species in an organism or biological sample, the method comprising adding to the organism or biological sample a probe molecule comprising a substrate and a label, which probe molecule can be incorporated into mycobacteria, the presence of mycobacteria being determined by a detector responsive to the presence of the label, optionally after applying a stimulus; suitable probe molecules include compounds comprising a label and a substrate, which label is can be detected by a detector responsive to the presence of the label, optionally after applying a stimulus, characterised by compound being able to engage with the active site of Antigen 85B (Ag85B) such that it can form simultaneous hydrogen bonds with two or more amino acids in the active site selected from Arg 43, Trp 264, Ser126, His 262 and Leu 42, or the corresponding amino acids in Antigen 85A (Ag85A) or Antigen 85C (Ag85C), at least one of which is with Ser126.

  一种用于确定生物体或生物样本中结核分枝杆菌种类存在的方法，该方法包括向生物体或生物样本中添加一种探针分子，该探针分子包括底物和标记，该探针分子可以被结核分枝杆菌所吸收，通过对标记的存在做出反应的探测器确定结核分枝杆菌的存在，可选地，在施加刺激后进行；适用的探针分子包括包含标记和底物的化合物，该标记可以被对标记的存在做出反应的探测器检测到，可选地，在施加刺激后进行，其特征在于该化合物能够与抗原85B（Ag85B）的活性位点结合，从而能够与所选活性位点中的两个或更多氨基酸同时形成氢键，所选活性位点包括Arg 43、Trp 264、Ser126、His 262和Leu 42，或者抗原85A（Ag85A）或抗原85C（Ag85C）中对应的氨基酸，其中至少一个与Ser126形成氢键。
• NEPHROTROPIC DRUGS
  申请人：Drug Delivery System Institute, Ltd.

  公开号：EP0953357A1

  公开（公告）日：1999-11-03

  Disclosed are a drug having renal selectivity and a drug carrier for specifically transporting a drug supported thereon to a kidney. A segment structure specifically recognizable in the kidney is utilized. More specifically, since a segment structure represented by formula (I) is kidney-oriented, introduction of a drug into a molecule having the segment structure can provide a renal targeting drug. A compound, which has the segment structure and can support a drug thereon, can be utilized as a drug carrier which can specifically transport a drug supported thereon to the kidney.         A-U-V-     (I) wherein A represents glycosyl, such as glucosyl, mannosyl, or 2-deoxy-glucosyl; U represents O, S, or NH; and V represents an aromatic hydrocarbon or a straight-chain or branched C1-18 aliphatic hydrocarbon.

  本发明涉及一种具有肾脏选择性的药物和一种药物载体，用于将支持在其上的药物专门运输到肾脏。利用在肾脏中特别可识别的片段结构。更具体地说，由式（I）表示的片段结构是以肾脏为导向的，将药物引入具有该片段结构的分子中可以提供肾脏靶向药物。具有该片段结构并能支持药物的化合物可用作药物载体，可将支持在其上的药物专门运输到肾脏。其中，A代表糖基，如葡萄糖基、甘露糖基或2-脱氧葡萄糖基；U代表O、S或NH；V代表芳香族碳氢化合物或直链或支链C1-18脂肪族碳氢化合物。
• DETECTION OF MYCOBACTERIA
  申请人：Backus Keriann Marie

  公开号：US20120263649A1

  公开（公告）日：2012-10-18

  A method for determining the presence of mycobacteria species in an organism or biological sample, the method comprising adding to the organism or biological sample a probe molecule comprising a substrate and a label, which probe molecule can be incorporated into mycobacteria, the presence of mycobacteria being determined by a detector responsive to the presence of the label, optionally after applying a stimulus; suitable probe molecules include compounds comprising a label and a substrate, which label is can be detected by a detector responsive to the presence of the label, optionally after applying a stimulus, characterised by compound being able to engage with the active site of Antigen 85B (Ag85B) such that it can form simultaneous hydrogen bonds with two or more amino acids in the active site selected from Arg 43, Trp 264, Ser126, His 262 and Leu 42, or the corresponding amino acids in Antigen 85A (Ag85A) or Antigen 85C (Ag85C), at least one of which is with Ser126.

  一种用于确定生物体或生物样本中结核分枝杆菌物种存在的方法，该方法包括向生物体或生物样本中添加一种探针分子，该探针分子包括底物和标签，该探针分子可以被结核分枝杆菌所包含，通过对响应标签存在的探测器进行检测来确定结核分枝杆菌的存在，可选地，在施加刺激后进行检测；适当的探针分子包括包含标签和底物的化合物，该标签可以被响应标签存在的探测器检测到，可选地，在施加刺激后进行检测，其特征在于该化合物能够与抗原85B（Ag85B）的活性位点发生作用，使其能够与活性位点中的Arg 43、Trp 264、Ser126、His 262和Leu 42中选择的两个或更多氨基酸同时形成氢键，或与抗原85A（Ag85A）或抗原85C（Ag85C）中的相应氨基酸形成氢键，其中至少有一个与Ser126形成氢键。
• TRACERS FOR MONITORING THE ACTIVITY OF SODIUM/GLUCOSE COTRANSPORTERS IN HEALTH AND DISEASE
  申请人：Wright Ernest M.

  公开号：US20100008856A1

  公开（公告）日：2010-01-14

  Radiolabeled tracers for sodium/glucose cotransporters (SGLTs), their synthesis, and their use are provided. The tracers are methyl or ethyl pyranosides having an equatorial hydroxyl group at carbon-2 and a C1 preferred conformation, radio-labeled with 18 F, 123 I, or 124 I, or free hexoses radiolabeled with 18 F, 123 I, or 124 I. Also provided are in vivo and in vitro techniques for using these and other tracers as analytical and diagnostic tools to study glucose transport, in health and disease, and to evaluate therapeutic interventions.

  提供了钠/葡萄糖共转运体（SGLT）的放射性标记示踪剂，它们的合成和使用。这些示踪剂是甲基或乙基吡喃糖，具有2碳处的赤道羟基和C1优先构象，放射性标记为18F，123I或124I，或放射性标记为18F，123I或124I的自由己糖。还提供了使用这些和其他示踪剂作为分析和诊断工具研究葡萄糖转运的体内和体外技术，在健康和疾病中，并评估治疗干预措施。
• Fluoro-substituted epipodophyllotoxin glucosides
  申请人：Bristol-Myers Squibb Company

  公开号：EP0358197A2

  公开（公告）日：1990-03-14

  The present invention provides antitumor fluoro-substituted 4'-demethylepipodophyllotoxin glucosides.

  本发明提供了抗肿瘤的氟代 4'-demethylepipodophyllotoxin 葡萄糖苷。