5-deoxy-5-fluoro-D-xylofuranose | 34147-21-2

• 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-xylofuranose
• 英文别名: 5-fluoro-5-deoxy-D-xylose；5-fluoro-D-5-deoxy-xylose；5-fluoro-ξ-D-5-deoxy-xylofuranose；(3R,4R,5S)-5-(fluoromethyl)oxolane-2,3,4-triol
• CAS: 34147-21-2
• 化学式: C₅H₉FO₄
• 分子量: 152.122
• InChiKey: HJCLMZBFWLNCPM-IOVATXLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-deoxy-5-fluoro-D-xylofuranose 在 potassium dihydrogenphosphate 、 Sweetzyme T 作用下， 以 水 为溶剂， 反应 3.0h， 生成 5-deoxy-5-fluoro-D-threo-pentulose
  参考文献：
  名称：

  The identification of (3R,4S)-5-fluoro-5-deoxy-d-ribulose-1-phosphate as an intermediate in fluorometabolite biosynthesis in Streptomyces cattleya

  摘要：

  (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-19{H-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。

  DOI：

  10.1016/j.bioorg.2007.04.001
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 N-溴代丁二酰亚胺(NBS) 、 二乙胺基三氟化硫 、 氢气 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 5-deoxy-5-fluoro-D-xylofuranose
  参考文献：
  名称：

  Binding and catalysis by yeast aldose reductase: A substrate-analog approach with new aldose derivatives

  摘要：

  5-Deoxy-D-xylofuranose derivatives and a range of new 5,6-dideoxy analogs of D-glucofuranose bearing azido or fluoro substituents were synthesised and employed as substrates of the NADH-dependent aldehyde reduction catalysed by yeast aldose reductase. In terms of catalytic efficiencies, these products proved to be superior to the parent compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00255-3

文献信息

• Preference for Axial <i>N</i>-Alkylation of Tetrahydro-1,3-oxazines and Hexahydropyrimidines:  Manifestation of a Kinetic Anomeric Effect
  作者：David A. Berges、Jianmei Fan、Sylvie Devinck、Kendall Mower

  DOI：10.1021/jo991752i

  日期：2000.2.1

  α-anomer is ascribed principally to a kinetic anomeric effect that destabilizes the transition state for equatorial N-alkylation and formation of the β-anomer. The α-anomer is principally formed by axial N-alkylation. Reaction of meso-2,4-pentanediamine with 5-bromo-5-deoxy-d-xylose in aqueous solution gives octahydropyrido[1,2-a]pyrimidine-7,8,9-triols 16α and 17β, which cannot interconvert. In this

  3-氨基-1-丙醇与 5-溴-5-脱氧-d-木糖在水溶液中反应得到异头六氢吡啶并[2,1-b][1,3]恶嗪-7,8,9-三醇2α和2β。当通过 1H NMR 监测该反应时，观察到 α-异头物的形成速度快 20 倍，但 β-异头物更稳定 (Kβ/α = 7.3)。评估了形成这些产物的反应途径，并确定非对映体四氢-1,3-恶嗪中间体的 N-烷基化是区分步骤。α-异头物的更快形成主要归因于动力学异头效应，该效应使赤道N-烷基化的过渡态和β-异头物的形成不稳定。α-异头物主要通过轴向N-烷基化形成。meso-2,4-pentanediamine 与 5-bromo-5-deoxy-d-xylose 在水溶液中反应得到八氢吡啶并[1, 2-a]pyrimidine-7,8,9-triols 16α 和 17β，它们不能相互转化。在这种情况下，16α 的形成速度是 17β 形成速度的两倍。这种费率差异归因于
• 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.
• Fluorocarbohydrates—XXI
  作者：P.W. Kent、R.C. Young

  DOI：10.1016/s0040-4020(01)98133-5

  日期：1971.1
• Binding and catalysis by yeast aldose reductase: A substrate-analog approach with new aldose derivatives
  作者：Philipp Hadwiger、Peter Mayr、Andreas Tauss、Arnold E Stütz、Bernd Nidetzky

  DOI：10.1016/s0960-894x(99)00255-3

  日期：1999.6

  5-Deoxy-D-xylofuranose derivatives and a range of new 5,6-dideoxy analogs of D-glucofuranose bearing azido or fluoro substituents were synthesised and employed as substrates of the NADH-dependent aldehyde reduction catalysed by yeast aldose reductase. In terms of catalytic efficiencies, these products proved to be superior to the parent compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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。