5-deoxy-5-fluoro-D-threo-pentulose | 144425-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-deoxy-5-fluoro-D-threo-pentulose
• 英文别名: 5-fluoro-5-deoxy-D-xylulose；5-deoxy-5-fluoro-D-xylulose；(3S,4S)-5-fluoro-1,3,4-trihydroxypentan-2-one
• CAS: 144425-61-6
• 化学式: C₅H₉FO₄
• 分子量: 152.122
• InChiKey: DZPAPJMTQBXJAM-WUJLRWPWSA-N

物化性质

• 沸点：
  399.0±37.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-deoxy-5-fluoro-1,2-O-isopropylidene-α-D-xylofuranose 在 Amberlite IR-120 [H⁺] ion-exchange resin 、 immobilised glucose isomerase EC 5.3.1.5 (Sweetzyme T) 、 magnesium sulfate 作用下， 以 水 、 乙腈 为溶剂， 生成 5-deoxy-5-fluoro-D-threo-pentulose
  参考文献：
  名称：

  Synthesis of 5,6-dimodified open-chain d-fructose derivatives and their properties as substrates of bacterial polyol dehydrogenase

  摘要：

  5-Deoxy-5-fluoro-D-xylulose as well as a range of new 5,6-dimodifed open-chain analogues of D-fructose, namely the 5,6-diazido-5,6-dideoxy, 6-azido-5,6-dideoxy, 6-azido-5,6-dideoxy-5-fluoro, 5,6-dideoxy-5-fluoro, 5,6-dideoxy-6-fluoro and 5,6-dideoxy-5,6-difluoro derivatives, were synthesised employing glucose isomerase catalysed isomerisation of the corresponding D-xylo- and D-glucofuranoses as a key step. New compounds as well as some previously reported analogues such as 5-azido-5,6-dideoxy-6-fluoro-D- fructose were shown to be excellent substrates of polyol dehydrogenase from Burkholderia cepacia DSM 50181 with K-m values two orders of magnitude smaller than the corresponding natural substrates. (C) 2000 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00526-1

文献信息

• Preparation of optically pure L-2-hydroxyaldehydes with yeast transketolase
  作者：Franz Effenberger、Volker Null、Thomas Ziegler

  DOI：10.1016/s0040-4039(00)79121-0

  日期：1992.9

  L-2-Hydroxyaldehydes L-3 with a great variety of substituents in 3-position are obtained in good chemical and excellent optical yields by kinetic resolution in the transketolase-catalyzed reaction of racemic 2-hydroxyaldehydes with lithium hydroxypyruvate 4 where only the enantiomer (R)-3 reacts to 5-deoxy-D-xyluloses 5.

  L-2-羟基醛L- 3在3位上有很大的各种取代基以良好的化学和由外消旋2-羟基醛的转酮酶-催化反应动力学拆分良好的光学收率与锂羟基丙酮酸得到4，其中只对映异构体（R）-3与5-脱氧-D-木酮糖5反应。
• The identification of (3R,4S)-5-fluoro-5-deoxy-d-ribulose-1-phosphate as an intermediate in fluorometabolite biosynthesis in Streptomyces cattleya
  作者：Mayca Onega、Ryan P. McGlinchey、Hai Deng、John T.G. Hamilton、David O’Hagan

  DOI：10.1016/j.bioorg.2007.04.001

  日期：2007.10

  (3R,4S)-5-Fluoro-5-deoxy-D-ribulose-1-phosphate (5-FDRulP) has been identified as the third fluorinated intermediate on the biosynthetic pathway to fluoroacetate and 4-fluorothreonine in Streptomyces cattleya. 5-FDRulP is generated after formation of 5 '-fluoro-5 '-deoxyadenosine (5 '-FDA) and then phosphorolysis of 5 '-FDA to 5-fluoro-5-deoxy-D-ribose-1-phosphate (5-FDRP) by the action of a purine nucleoside phosphorylase. An isomerase mediates the conversion of 5-FDRP to 5-FDRulP. The identity of the (3R,4S) diastereoisomer of 5-FDRulP was established by comparative F-19H-1} NMR studies whereby 5-FDRulP that accumulated in a cell free extract of S. cattleya, was treated with a phytase to generate the non-phosphorylated sugar, 5-fluoro-5-deoxy-D-ribulose (5-FDRul). This S. cattleya product was compared to the product of an in-vitro biotransformation where separately 5-fluoro5-deoxy-D-ribose and 5-fluoro-5-deoxy-D-xylose were converted to 5-fluoro-5-deoxy-D-ribulose and 5-fluoro-5-deoxy-D-xylulose respectively by the action of glucose isomerase. It was demonstrated that 5-fluoro-5-deoxy-D-ribose gave the identical diastereoisomer to that observed from 5-FDRulP. (c) 2007 Elsevier Inc. All rights reserved.

  (3R,4S)-5-氟-5-脱氧-D-核糖醇-1-磷酸酯（5-FDRulP）在链霉菌cattleya的氟乙酸和4-氟苏氨酸生物合成途径中被鉴定为第三个含氟的中间体。5-FDRulP是在5'-氟-5'-脱氧腺苷（5'-FDA）形成之后，由嘌呤核苷磷酸化酶作用使5'-FDA发生磷酸水解生成5-氟-5-脱氧-D-核糖-1-磷酸（5-FDRP），随后通过异构酶的作用将5-FDRP转化为5-FDRulP。5-FDRulP的(3R,4S)异构体身份通过比较F-19H-1} NMR研究得以确定。具体来说，链霉菌cattleya细胞提取物中积累的5-FDRulP经磷酸酶处理生成非磷酸化糖5-氟-5-脱氧-D-核糖醇（5-FDRul）。该链霉菌cattleya产物与体外生物转化产物进行比较，其中5-氟-5-脱氧-D-核糖和5-氟-5-脱氧-D-木糖分别在葡萄糖异构酶作用下转化为5-氟-5-脱氧-D-核糖醇和5-氟-5-脱氧-D-木糖醇。结果表明，5-氟-5-脱氧-D-核糖生成了与5-FDRulP中相同的异构体。 © 2007 Elsevier Inc. 保留所有权利。
• Synthesis of 5,6-dimodified open-chain d-fructose derivatives and their properties as substrates of bacterial polyol dehydrogenase
  作者：Philipp Hadwiger、Peter Mayr、Bernd Nidetzky、Arnold E Stütz、Andreas Tauss

  DOI：10.1016/s0957-4166(99)00526-1

  日期：2000.2

  5-Deoxy-5-fluoro-D-xylulose as well as a range of new 5,6-dimodifed open-chain analogues of D-fructose, namely the 5,6-diazido-5,6-dideoxy, 6-azido-5,6-dideoxy, 6-azido-5,6-dideoxy-5-fluoro, 5,6-dideoxy-5-fluoro, 5,6-dideoxy-6-fluoro and 5,6-dideoxy-5,6-difluoro derivatives, were synthesised employing glucose isomerase catalysed isomerisation of the corresponding D-xylo- and D-glucofuranoses as a key step. New compounds as well as some previously reported analogues such as 5-azido-5,6-dideoxy-6-fluoro-D- fructose were shown to be excellent substrates of polyol dehydrogenase from Burkholderia cepacia DSM 50181 with K-m values two orders of magnitude smaller than the corresponding natural substrates. (C) 2000 Elsevier Science Ltd, All rights reserved.