vicibactin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: vicibactin
• 英文别名: Vicibactin；N-[(2R,9R,12R,19R,22R,29R)-19,29-diacetamido-5,15,25-trihydroxy-2,12,22-trimethyl-4,10,14,20,24,30-hexaoxo-1,11,21-trioxa-5,15,25-triazacyclotriacont-9-yl]acetamide
• 化学式: C₃₃H₅₄N₆O₁₅
• 分子量: 774.823
• InChiKey: NEZSNYPOAQRZDV-ZXXBMJRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  54
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  288
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  ammonium iron(II) sulfate hexahydrate 、 vicibactin 以 水 为溶剂， 生成 ferrivicibactin
  参考文献：
  名称：

  Enzymatic Tailoring of Ornithine in the Biosynthesis of the Rhizobium Cyclic Trihydroxamate Siderophore Vicibactin

  摘要：

  To acquire iron, the N-2-fixing, symbiotic bacterium Rhizobium sp. produce the cyclic trihydroxamate siderophore vicibactin, containing a 30-membered trilactone scaffold. Herein we report the overproduction and purification of the six proteins VbsACGOLS in the bacterial host Escherichia coli and the reconstitution of the biosynthesis of vicibactin from primary metabolites. The flavoprotein VbsO acts as a pathway-initiating L-ornithine M-hydroxylase, followed by VbsA, which transfers (R)-3-hydroxybutyryl- from the CoA thioester to N-6-hydroxyornithine to yield N-6-((R)-3-hydroxybutyryl)-N-6-hydroxy-L-orinithine. VbsL is a PLP-dependent epimerase acting at C-2 of the 10 atom monomer unit. VbsS, a nonribosomal peptide synthetase freestanding module, then activates N-6-((R)-3-hydroxybutyryl)-N-6-hydroxy-D-ornithine as the AMP anhydride on the way to cyclotrimerization to the vicibactin scaffold. The last step, tris-acetylation of the C-2 amino group of desacetyl-D-vicibactin to the mature siderophore vicibactin, is catalyzed distributively by VbsC, using three molecules of acetyl-CoA.

  DOI：

  10.1021/ja9056008
• 作为产物：
  描述：

  desacetylvicibactin 、 乙酰辅酶A 在 Rhizobium etli CFN₄₂ ATCC₅₁₂₅₁ VbsC N₂-acetyltransferase 作用下， 生成 vicibactin 、 monoacetylated vicibactin homolog 、 diacetylated vicibactin homolog
  参考文献：
  名称：

  Enzymatic Tailoring of Ornithine in the Biosynthesis of the Rhizobium Cyclic Trihydroxamate Siderophore Vicibactin

  摘要：

  To acquire iron, the N-2-fixing, symbiotic bacterium Rhizobium sp. produce the cyclic trihydroxamate siderophore vicibactin, containing a 30-membered trilactone scaffold. Herein we report the overproduction and purification of the six proteins VbsACGOLS in the bacterial host Escherichia coli and the reconstitution of the biosynthesis of vicibactin from primary metabolites. The flavoprotein VbsO acts as a pathway-initiating L-ornithine M-hydroxylase, followed by VbsA, which transfers (R)-3-hydroxybutyryl- from the CoA thioester to N-6-hydroxyornithine to yield N-6-((R)-3-hydroxybutyryl)-N-6-hydroxy-L-orinithine. VbsL is a PLP-dependent epimerase acting at C-2 of the 10 atom monomer unit. VbsS, a nonribosomal peptide synthetase freestanding module, then activates N-6-((R)-3-hydroxybutyryl)-N-6-hydroxy-D-ornithine as the AMP anhydride on the way to cyclotrimerization to the vicibactin scaffold. The last step, tris-acetylation of the C-2 amino group of desacetyl-D-vicibactin to the mature siderophore vicibactin, is catalyzed distributively by VbsC, using three molecules of acetyl-CoA.

  DOI：

  10.1021/ja9056008

文献信息

• Enzymatic Tailoring of Ornithine in the Biosynthesis of the <i>Rhizobium</i> Cyclic Trihydroxamate Siderophore Vicibactin
  作者：John R. Heemstra、Christopher T. Walsh、Elizabeth S. Sattely

  DOI：10.1021/ja9056008

  日期：2009.10.28

  To acquire iron, the N-2-fixing, symbiotic bacterium Rhizobium sp. produce the cyclic trihydroxamate siderophore vicibactin, containing a 30-membered trilactone scaffold. Herein we report the overproduction and purification of the six proteins VbsACGOLS in the bacterial host Escherichia coli and the reconstitution of the biosynthesis of vicibactin from primary metabolites. The flavoprotein VbsO acts as a pathway-initiating L-ornithine M-hydroxylase, followed by VbsA, which transfers (R)-3-hydroxybutyryl- from the CoA thioester to N-6-hydroxyornithine to yield N-6-((R)-3-hydroxybutyryl)-N-6-hydroxy-L-orinithine. VbsL is a PLP-dependent epimerase acting at C-2 of the 10 atom monomer unit. VbsS, a nonribosomal peptide synthetase freestanding module, then activates N-6-((R)-3-hydroxybutyryl)-N-6-hydroxy-D-ornithine as the AMP anhydride on the way to cyclotrimerization to the vicibactin scaffold. The last step, tris-acetylation of the C-2 amino group of desacetyl-D-vicibactin to the mature siderophore vicibactin, is catalyzed distributively by VbsC, using three molecules of acetyl-CoA.