(3S,4R,5R)-3,4,5,6-四羟基己烷-2-酮 | 32785-92-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (3S,4R,5R)-3,4,5,6-四羟基己烷-2-酮
• 英文名称: 1-deoxy-D-frucrose
• 英文别名: 1-deoxy-D-fructose；D-1-deoxy-fructose；1-deoxy D-fructose；1-deoxyfructose；(3S,4R,5R)-3,4,5,6-tetrahydroxyhexan-2-one
• CAS: 32785-92-5
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: IXDZFGATLNCIOI-HSUXUTPPSA-N

物化性质

• 沸点：
  455.3±45.0 °C(Predicted)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  11
• 可旋转键数：
  4
• 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：
  5

安全信息

• 海关编码：
  2914400090

反应信息

• 作为产物：
  描述：

  1-deoxy-D-psicose 在 immobilized D-tagatose-3-epimerase 作用下， 以 水 为溶剂， 反应 12.0h， 以75%的产率得到(3S,4R,5R)-3,4,5,6-四羟基己烷-2-酮
  参考文献：
  名称：

  Conversion of l-rhamnose into ten of the sixteen 1- and 6-deoxyketohexoses in water with three reagents: d-tagatose-3-epimerase equilibrates C3 epimers of deoxyketoses

  摘要：

  The efficient isomerization of L-rhamnose [the only cheaply available deoxy hexose] to 1-deoxy-L-psicose, 1-deoxy-D-psicose, 1-deoxy-L-fructose, 1-deoxy-D-fructose, 1-deoxy-L-tagatose, 6-deoxy-L-psicose, 6-deoxy-D-psicose, 6-deoxy-L-fructose, 6-deoxy-D-fructose, and 6-deoxy-L-tagatose is described. The conversion of rhamnose to ten of the sixteen 1- and 6-deoxyketohexoses is accomplished in water in three steps. The range of substrates for D-tagatose-3-epimerase (DTE) is extended to 1- and 6-deoxyketoses. An authentic sample of 6-deoxy-D-psicose is prepared from D-psicose. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.024

文献信息

• DEOXYKETOHEXOSE ISOMERASE AND METHOD FOR PRODUCING DEOXYHEXOSE AND DERIVATIVE THEREOF USING SAME
  申请人：Izumori Ken

  公开号：US20100105885A1

  公开（公告）日：2010-04-29

  Providing 1- or 6-deoxy products corresponding to all of aldohexoses, ketohexoses and sugar alcohols, as based on Deoxy-Izumoring, as well as a method for systematically producing those products. A method for producing deoxyketohexose and a derivative thereof using a deoxyketohexose isomerase derived from Pseudomonas cichorii ST-24 (FERM BP-2736), comprising epimerizing 1-deoxy D-ketohexose or 6-deoxy D-ketohexose or 1-deoxy L-ketohexose or 6-deoxy L-ketohexose at position 3 to produce the individually corresponding 1-deoxy D-ketohexose or 6-deoxy D-ketohexose or 1-deoxy L-ketohexose or 6-deoxy L-ketohexose as an intended product.

  提供对应于所有己醛糖、己酮糖和糖醇的1-或6-去氧产物，基于去氧-Izumoring，以及一种系统生产这些产物的方法。一种使用来自Pseudomonas cichoriiST-24（FERM BP-2736）的去氧己酮糖异构酶生产去氧己酮糖及其衍生物的方法，包括将1-去氧D-己酮糖或6-去氧D-己酮糖或1-去氧L-己酮糖或6-去氧L-己酮糖在3号位置上对映异构化为各自对应的1-去氧D-己酮糖或6-去氧D-己酮糖或1-去氧L-己酮糖或6-去氧L-己酮糖作为预期产物。
• A Mutant D-Fructose-6-Phosphate Aldolase (Ala129Ser) with Improved Affinity towards Dihydroxyacetone for the Synthesis of Polyhydroxylated Compounds
  作者：José A. Castillo、Christine Guérard-Hélaine、Mariana Gutiérrez、Xavier Garrabou、Martine Sancelme、Melanie Schürmann、Tomoyuki Inoue、Virgil Hélaine、Franck Charmantray、Thierry Gefflaut、Laurence Hecquet、Jesús Joglar、Pere Clapés、Georg A. Sprenger、Marielle Lemaire

  DOI：10.1002/adsc.200900772

  日期：——

  is particularly useful in carboligation multi‐step cascade synthesis of polyhydroxylated complex compounds. Production of the mutant protein was also improved for its convenient use in synthesis. Several carbohydrates and nitrocyclitols were efficiently prepared, demonstrating the versatile potential of FSA A129S as biocatalyst in organic synthesis.

  研究了大肠杆菌D-果糖-6-磷酸醛缩酶（FSA）的突变体FSA A129S，其对醛醇加成反应中供体底物二羟基丙酮（DHA）的催化效率得到了提高，可用于合成应用。FSA A129S的DHA的k cat / K M值比FSA野生型（FSA wt）高出17倍。另一方面，对于羟丙酮作为供体底物，发现FSA A129S的效率比FSA wt低3.5倍。此外，FSA A129S还接受了乙醇醛（GA）作为供体底物，其亲和力比FSA wt低3.3倍。两种FSA wt的差异选择性FSA A129S和GA的FSA A129S使它们成为互补的生物催化剂，可以控制供体和受体的作用，这在多羟基化复合化合物的碳多步级联碳多步合成中特别有用。突变蛋白的生产也得到了改进，因为它可方便地用于合成。有效地制备了几种碳水化合物和硝基环糖醇，证明了FSA A129S作为有机合成中的生物催化剂具有多种用途。
• 3-deoxyglucosone and skin
  申请人：——

  公开号：US20030219440A1

  公开（公告）日：2003-11-27

  The invention relates to a method of removing 3-deoxyglucosone and other alpha-dicarbonyl sugars from skin. The invention further relates to methods of inhibiting production and function of 3-deoxyglucosone and other alpha-dicarbonyl sugars in skin. The invention also relates to methods of treating 3-deoxyglucosone and other alpha-dicarbonyl sugars associated diseases and disorders of skin.

  该发明涉及一种从皮肤中去除3-去氧葡萄糖酮和其他α-二酮糖的方法。该发明还涉及抑制皮肤中3-去氧葡萄糖酮和其他α-二酮糖的产生和功能的方法。该发明还涉及治疗与皮肤相关的3-去氧葡萄糖酮和其他α-二酮糖相关疾病和障碍的方法。
• Novel nucleosides having bicyclic sugar moiety
  申请人：——

  公开号：US20030028013A1

  公开（公告）日：2003-02-06

  Conformationally restricted 2′, 4′-bridged nucleoside analogues are described herein. The compounds can be prepared by cyclization at C2′ and C4′ of nucleosides through a linker or linking molecule. These novel nucleosides have a desired, locked sugar pucker and are potentially useful as pharmaceutical ingredients, and especially for use in treatment of HCV.

  本文描述了构象受限的2′，4′-桥接核苷类似物。这些化合物可以通过在核苷的C2′和C4′处通过连接物或连接分子进行环化来制备。这些新型核苷具有所需的锁定糖环形，并且可能作为药用成分，特别是用于HCV的治疗。
• Compounds and methods for therapeutic intervention in preventing diabetic complications and procedures for assessing a diabetic's risk of developing complications and determining the efficacy of therapeutic intervention
  申请人：——

  公开号：US20020111291A1

  公开（公告）日：2002-08-15

  Disclosed is a class of compounds which inhibit the enzymatic conversion of fructose-lysine into fructose-lysine-3-phosphate in an ATP dependent reaction in a newly discovered metabolic pathway. According to the normal functioning on this pathway, fructose-lysine-3-phosphate (FL3P) is broken down to form free lysine, inorganic phosphate and 3-deoxyglucosone (3DG), the latter being a reactive protein modifying agent. 3DG can be detoxified by reduction to 3-deoxyfructose (3DF), or it can react with endogenous proteins to form advanced glycation end-product modified proteins (AGE-proteins), which are believed to be a contributing cause of diabetic complications. Also disclosed are therapeutic methods of using such inhibitors to reduce formation of AGE-proteins and thereby lessen, reduce and delay diabetic complications and the effects of glycogen storage diseases, including Fanconi's syndrome. Methods for assessing a diabetic's risk of developing complications and for determining the efficacy of the disclosed inhibitor therapy by measuring the ratio of 3DG to 3DF in a biological sample following an oral dose of a fructose-lysine-containing food product are also disclosed.

  本文披露了一类化合物，可以抑制酶催化将果糖赖氨酸转化为果糖赖氨酸-3-磷酸酯的反应，这是一种新发现的代谢途径中依赖ATP的反应。根据该途径的正常功能，果糖赖氨酸-3-磷酸酯（FL3P）被分解为游离赖氨酸、无机磷酸盐和3-脱氧葡萄糖酮（3DG），后者是一种具有反应性的蛋白质修饰剂。3DG可以通过还原为3-脱氧果糖（3DF）来解毒，也可以与内源蛋白质反应形成高级糖基化终产物修饰的蛋白质（AGE-蛋白），据信这是糖尿病并发症的一个促发因素。此外，还披露了使用这种抑制剂的治疗方法，以减少AGE-蛋白的形成，从而减轻、减少和延迟糖尿病并发症和糖原贮积病（包括范科尼综合征）的影响。还披露了通过在口服含果糖赖氨酸的食品后测量生物样品中3DG与3DF比值来评估糖尿病患者发生并发症的风险和确定披露的抑制剂疗法的疗效的方法。