(2S)-2,3-dihydroxy-4-nitrobutanal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2,3-dihydroxy-4-nitrobutanal
• 化学式: C₄H₇NO₅
• 分子量: 149.103
• InChiKey: PBGSJEXZBVDWKP-SRBOSORUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-二羟基丙酮 、 (2S)-2,3-dihydroxy-4-nitrobutanal 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 17.0h， 以50%的产率得到(1S,2S,3R,4S,5R,6R)-1-(hydroxymethyl)-6-nitrocyclohexane-1,2,3,4,5-pentol
  参考文献：
  名称：

  Fructose-6-phosphate aldolases as versatile biocatalysts for nitrocyclitol syntheses

  摘要：

  Efficient and stereoselective polyhydroxylated nitrocyclitol syntheses were performed via biocatalysed aldol reactions. The key step was based on a one-pot/one-enzyme cascade reaction process where two reactions occur: aldolase-catalysed aldolisation and spontaneous intramolecular nitroaldolisation. The synthetic methodology was investigated using fructose-6-phosphate aldolase A129S for the synthesis of known nitrocyclitols. Improvements were obtained which involved less steps and increased yields. Several new nitrocyclitols were also prepared using hydroxyacetone (HA) as the donor and FSA wt. From nitrocyclitol stereochemical analyses, the intramolecular nitro-Henry reaction stereoselectivity was dependent on the donor substrate used, HA or dihydroxyacetone (DHA). Whereas DHA provided two stereoisomers, four were obtained using HA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.016
• 作为产物：
  描述：

  (3S)-4,4-diethoxy-1-nitrobutan-2,3-diol 在 cation exchange resin Dowex 50x8, H⁺ form 作用下， 以 水 为溶剂， 生成 (2S)-2,3-dihydroxy-4-nitrobutanal
  参考文献：
  名称：

  Fructose-6-phosphate aldolases as versatile biocatalysts for nitrocyclitol syntheses

  摘要：

  Efficient and stereoselective polyhydroxylated nitrocyclitol syntheses were performed via biocatalysed aldol reactions. The key step was based on a one-pot/one-enzyme cascade reaction process where two reactions occur: aldolase-catalysed aldolisation and spontaneous intramolecular nitroaldolisation. The synthetic methodology was investigated using fructose-6-phosphate aldolase A129S for the synthesis of known nitrocyclitols. Improvements were obtained which involved less steps and increased yields. Several new nitrocyclitols were also prepared using hydroxyacetone (HA) as the donor and FSA wt. From nitrocyclitol stereochemical analyses, the intramolecular nitro-Henry reaction stereoselectivity was dependent on the donor substrate used, HA or dihydroxyacetone (DHA). Whereas DHA provided two stereoisomers, four were obtained using HA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.016

文献信息

• l-Rhamnulose-1-phosphate and l-fuculose-1-phosphate aldolase mediated multi-enzyme cascade systems for nitrocyclitol synthesis
  作者：Flora Camps Bres、Christine Guérard-Hélaine、Virgil Hélaine、Carlos Fernandes、Israel Sánchez-Moreno、Mounir Traïkia、Eduardo García-Junceda、Marielle Lemaire

  DOI：10.1016/j.molcatb.2014.10.016

  日期：2015.4

  One-pot multistep stereoselective cascade reactions were implemented for the straightforward synthesis of various nitrocyclitols. Two kinases, an aldolase and a phosphatase were involved in this process, together with a spontaneous intramolecular Henry reaction to provide the nitrocyclitol moiety. The C-C bond formation catalysed by the aldolase and the nitroaldol reactions were key steps to build the carbocycle stereoselectively. The aldolase acceptor substrates were all 4-nitrobutanal structurally based, either hydroxylated or unsubstituted at the C2 and/or C3 positions. L-Fuculose-1-phosphate aldolase (FucA) catalysed the formation of the expected (R,R)- or D-erythro aldol, except in the case of 4-nitrobutanal, from which the epimeric (R,S)- or L-threo aldol was also formed. L-Rhamnulose-1-phosphate aldolase consistently formed the expected (R,S)- or L-threo aldol together with a minor amount of (R,R)- or D-elythro aldol. The intramolecular Henry reaction was also found to be stereoselective, occurring spontaneously once the aldol was formed due to the presence of both ketone and a terminally positioned nitro group. The combination of this set of reactions successfully furnished 11 nitrocyclitols which have not been described previously in the literature. (C) 2014 Elsevier B.V. All rights reserved.
• Fructose-6-phosphate aldolases as versatile biocatalysts for nitrocyclitol syntheses
  作者：Flora Camps Bres、Christine Guérard-Hélaine、Carlos Fernandes、José A. Castillo、Marielle Lemaire

  DOI：10.1016/j.tetasy.2013.07.016

  日期：2013.9

  Efficient and stereoselective polyhydroxylated nitrocyclitol syntheses were performed via biocatalysed aldol reactions. The key step was based on a one-pot/one-enzyme cascade reaction process where two reactions occur: aldolase-catalysed aldolisation and spontaneous intramolecular nitroaldolisation. The synthetic methodology was investigated using fructose-6-phosphate aldolase A129S for the synthesis of known nitrocyclitols. Improvements were obtained which involved less steps and increased yields. Several new nitrocyclitols were also prepared using hydroxyacetone (HA) as the donor and FSA wt. From nitrocyclitol stereochemical analyses, the intramolecular nitro-Henry reaction stereoselectivity was dependent on the donor substrate used, HA or dihydroxyacetone (DHA). Whereas DHA provided two stereoisomers, four were obtained using HA. (C) 2013 Elsevier Ltd. All rights reserved.