prop-2-enyl (E)-3-[[(4R)-2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl]amino]prop-2-enoate | 652976-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: prop-2-enyl (E)-3-[[(4R)-2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl]amino]prop-2-enoate
• CAS: 652976-09-5
• 化学式: C₁₅H₂₃NO₅
• 分子量: 297.351
• InChiKey: GTFQTAPFTKXENE-GUOLPTJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (E)-3-[[(4R)-2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl]amino]prop-2-enoate 在 bismuth(III) chloride 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 以75%的产率得到(R,E)-allyl 3-(2,4-dihydroxy-3,3-dimethylbutanamido)acrylate
  参考文献：
  名称：

  The Antibiotic CJ-15,801 Is an Antimetabolite that Hijacks and Then Inhibits CoA Biosynthesis

  摘要：

  The natural product CJ-15,801 is an inhibitor of Staphylococcus aureus, but not other bacteria. Its close structural resemblance to pantothenic acid, the vitamin precursor of coenzyme A (CoA), and its Michael acceptor moiety suggest that it irreversibly inhibits an enzyme involved in CoA biosynthesis or utilization. However, its mode of action and the basis for its specificity have not been elucidated to date. We demonstrate that CJ-15,801 is transformed by the uniquely selective S. aureus pantothenate kinase, the first CoA biosynthetic enzyme, into a substrate for the next enzyme, phosphopantothenoylcysteine synthetase, which is inhibited through formation of a tight-binding structural mimic of its native reaction intermediate. These findings reveal CJ-15,801 as a vitamin biosynthetic pathway antimetabolite with a mechanism similar to that of the sulfonamide antibiotics and highlight CoA biosynthesis as a viable antimicrobial drug target.

  DOI：

  10.1016/j.chembiol.2012.03.013
• 作为产物：
  描述：

  D-(-)-泛酰内酯 在 碳酸氢钠 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 氟苯 、 丙酮 、 甲苯 为溶剂， 反应 23.0h， 生成 prop-2-enyl (E)-3-[[(4R)-2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl]amino]prop-2-enoate
  参考文献：
  名称：

  通过用Dess-Martin高碘烷氧化酰胺和胺来合成酰亚胺，N-酰基乙烯基氨基甲酸酯和脲以及腈。

  摘要：

  DOI：

  10.1002/anie.200501853

文献信息

• Copper-Mediated Synthesis of <i>N</i>-Acyl Vinylogous Carbamic Acids and Derivatives:  Synthesis of the Antibiotic CJ-15,801
  作者：Chong Han、Ruichao Shen、Shun Su、John A. Porco

  DOI：10.1021/ol0360041

  日期：2004.1.1

  Copper(I)-mediated C-N bond formation has been employed to prepare both N-acyl vinylogous carbamic acids and ureas. The novel N-acyl vinylogous carbamic acid antibiotic, CJ-15,801, was synthesized using this methodology.
• [EN] A. PROCESS FOR THE PREPARATION OF AMINOACRYLIC ACID DERIVATIVES<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE DÉRIVÉS D'ACIDE AMINOACRYLIQUE
  申请人：COUNCIL OF SCIENT & IND RES AN INDIAN REGISTERED BODY INC UNDER THE REGISTRATION OF SOCIETIES ACT AC

  公开号：WO2013054366A8

  公开（公告）日：2013-05-30
• US9193674B2
  申请人：——

  公开号：US9193674B2

  公开（公告）日：2015-11-24
• Synthesis of Imides,N-Acyl Vinylogous Carbamates and Ureas, and Nitriles by Oxidation of Amides and Amines with Dess-Martin Periodinane
  作者：K. C. Nicolaou、Casey J. N. Mathison

  DOI：10.1002/anie.200501853

  日期：2005.9.19
• The Antibiotic CJ-15,801 Is an Antimetabolite that Hijacks and Then Inhibits CoA Biosynthesis
  作者：Renier van der Westhuyzen、Justin C. Hammons、Jordan L. Meier、Samira Dahesh、Wessel J.A. Moolman、Stephen C. Pelly、Victor Nizet、Michael D. Burkart、Erick Strauss

  DOI：10.1016/j.chembiol.2012.03.013

  日期：2012.5

  The natural product CJ-15,801 is an inhibitor of Staphylococcus aureus, but not other bacteria. Its close structural resemblance to pantothenic acid, the vitamin precursor of coenzyme A (CoA), and its Michael acceptor moiety suggest that it irreversibly inhibits an enzyme involved in CoA biosynthesis or utilization. However, its mode of action and the basis for its specificity have not been elucidated to date. We demonstrate that CJ-15,801 is transformed by the uniquely selective S. aureus pantothenate kinase, the first CoA biosynthetic enzyme, into a substrate for the next enzyme, phosphopantothenoylcysteine synthetase, which is inhibited through formation of a tight-binding structural mimic of its native reaction intermediate. These findings reveal CJ-15,801 as a vitamin biosynthetic pathway antimetabolite with a mechanism similar to that of the sulfonamide antibiotics and highlight CoA biosynthesis as a viable antimicrobial drug target.