4-(N-hydroxyamino)butanoic acid | 14469-03-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(N-hydroxyamino)butanoic acid
• 英文别名: 4-(N-hydroxyamino)butyric acid；4-Hydroxyamino-buttersaeure；4-(hydroxyamino)butanoic Acid
• CAS: 14469-03-5
• 化学式: C₄H₉NO₃
• 分子量: 119.12
• InChiKey: JOKBUWBIEABYKP-UHFFFAOYSA-N

物化性质

• 沸点：
  338.1±44.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(N-hydroxyamino)butanoic acid 、 甲乙酐 反应 12.0h， 以72%的产率得到4-(N-formyl-N-hydroxyamino)-butyric acid
  参考文献：
  名称：

  Evaluation of fosmidomycin analogs as inhibitors of the Synechocystis sp. PCC6803 1-deoxy-d-xylulose 5-phosphate reductoisomerase

  摘要：

  Analogs of the antibiotic fosmidomycin, an inhibitor of the methylerythritol phosphate pathway to isoprenoids, were synthesized and evaluated against the recombinant Synechocystis sp. PCC6803 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR). Fosfoxacin, the phosphate analog of fosmidomycin, and its acetyl congener were found to be more potent inhibitors of DXR than fosmidomycin. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.012
• 作为产物：
  描述：

  4-[N-benzyloxy-N-(toluene-4-sulfonyl)amino]butyric acid ethyl ester 在 盐酸 、 溶剂黄146 作用下， 以81%的产率得到4-(N-hydroxyamino)butanoic acid
  参考文献：
  名称：

  Evaluation of fosmidomycin analogs as inhibitors of the Synechocystis sp. PCC6803 1-deoxy-d-xylulose 5-phosphate reductoisomerase

  摘要：

  Analogs of the antibiotic fosmidomycin, an inhibitor of the methylerythritol phosphate pathway to isoprenoids, were synthesized and evaluated against the recombinant Synechocystis sp. PCC6803 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR). Fosfoxacin, the phosphate analog of fosmidomycin, and its acetyl congener were found to be more potent inhibitors of DXR than fosmidomycin. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.012

文献信息

• A general synthesis of N-hydroxyamino acids
  作者：Eberhard Buehler、George Bosworth Brown

  DOI：10.1021/jo01288a003

  日期：1967.2
• Evaluation of hadacidin analogues
  作者：Nidhi Tibrewal、Gregory I. Elliott

  DOI：10.1016/j.bmcl.2010.10.088

  日期：2011.1

  Several derivatives of hadacidin have been developed and evaluated for activity against adenylosuccinate synthetase. (C) 2010 Elsevier Ltd. All rights reserved.
• An efficient synthesis of N-monoalkylated hydroxylamines
  作者：Gábor Doleschall

  DOI：10.1016/s0040-4039(00)96265-8

  日期：——
• Evaluation of fosmidomycin analogs as inhibitors of the Synechocystis sp. PCC6803 1-deoxy-d-xylulose 5-phosphate reductoisomerase
  作者：Youn-Hi Woo、Roberta P.M. Fernandes、Philip J. Proteau

  DOI：10.1016/j.bmc.2005.11.012

  日期：2006.4

  Analogs of the antibiotic fosmidomycin, an inhibitor of the methylerythritol phosphate pathway to isoprenoids, were synthesized and evaluated against the recombinant Synechocystis sp. PCC6803 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR). Fosfoxacin, the phosphate analog of fosmidomycin, and its acetyl congener were found to be more potent inhibitors of DXR than fosmidomycin. (c) 2005 Elsevier Ltd. All rights reserved.