bacillibactin | 95536-41-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: bacillibactin
• 英文别名: Corynebactin；N-[2-[[(2R,3S,6R,7S,10R,11S)-7,11-bis[[2-[(2,3-dihydroxybenzoyl)amino]acetyl]amino]-2,6,10-trimethyl-4,8,12-trioxo-1,5,9-trioxacyclododec-3-yl]amino]-2-oxoethyl]-2,3-dihydroxybenzamide
• CAS: 95536-41-7
• 化学式: C₃₉H₄₂N₆O₁₈
• 分子量: 882.792
• InChiKey: RCQTVEFBFUNTGM-BDVHUIKKSA-N

物化性质

• 沸点：
  1351.3±65.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  63
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  375
• 氢给体数：
  12
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  bacillibactin 、 三氯化铁 以 盐酸 、 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  棒杆菌素和丝氨酸三内酯类似物：铁络合物的手性和分子模型。

  摘要：

  由于三价铁离子的水解使其在有氧，接近中性pH的环境中非常不溶，因此大多数细菌会产生铁载体来获取铁（一种基本营养素）。铁铁载体复合物的手性在细胞识别，摄取和利用中起重要作用。从革兰氏阳性细菌中分离出来的棒状杆菌素在结构上与Enterobactin类似，后者首先从革兰氏阴性细菌中分离出来，是众所周知的铁载体，但在三内酯骨架中含有L-苏氨酸而不是L-丝氨酸。棒杆菌素在每个螯合臂中还包含甘氨酸间隔单元。已经制备了具有肠杆菌素的三内酯环和棒杆菌素的甘氨酸间隔基的杂合类似物（丝氨酸-棒杆菌素）。通过分子建模（包括MM3和pBP86 / DN密度泛函理论计算）和圆二色性光谱，研究了肠杆菌素，棒杆菌素和杂合体的三种铁配合物的手性和相对构象稳定性。肠杆菌素形成Delta-铁复​​合物，而棒杆菌素为Lambda。杂合丝氨酸-棒状杆菌素形成近乎外消旋的混合物，而λ-构象异构体稍微过量。每个铁配合物具有四个可能的

  DOI：

  10.1021/ic025531y
• 作为产物：
  描述：

  2,3-dihydroxybenzoate 、 adenosine 5'-triphosphate 、 聚甘氨酸 、 L-苏氨酸 生成 adenosine 5'-monophosphate 、 bacillibactin 、 pyrophosphoric acid 、 氢(+1)阳离子 、 水
  参考文献：
  名称：

  The dhb Operon of Bacillus subtilisEncodes the Biosynthetic Template for the Catecholic Siderophore 2,3-Dihydroxybenzoate-Glycine-Threonine Trimeric Ester Bacillibactin

  摘要：

  Bacillus subtilis was reported to produce the catecholic siderophore itoic acid (2,3-dihydroxybenzoate (DHB)-glycine) in response to iron deprivation, However, by inspecting the DNA sequences of the genes dhbE, dhbB, and dhbF as annotated by the B, subtilis genome project to encode the synthetase complex for the siderophore assembly, various sequence errors within the dhbF gene were predicted and confirmed by re-sequencing. According to the corrected sequence, dhbF encodes a dimodular instead of a monomodular nonribosomal peptide synthetase, We have heterologously expressed, purified, and assayed the substrate selectivity of the recombinant proteins DhbB, DhbE, and DhbF, DhbE, a stand-alone adenylation domain of 59.9 kDa, activates, in an ATP-dependent reaction, I)HB, which is subsequently transferred to the free thiol group of the cofactor phosphopantetheine of the bifunctional isochorismate lyase/aryl carrier protein DhbB, The third synthetase, DhbF, is a dimodular nonribosomal peptide synthetase of 264 kDa that specifically adenylates threonine and, to a lesser extent, glycine and that covalently loads both amino acids onto their corresponding peptidyl carrier domains. To functionally link the dhb gene cluster to siderophore synthesis, we have disrupted the dhbF gene. Comparative mass spectrometric analysis of culture extracts from both the wild type and the dhbF mutant led to the identification of a mass peak at mit 881 ([M-H](1-)) that corresponds to a cyclic trimeric ester of DHB-glycine-threonine.

  DOI：

  10.1074/jbc.m009140200

文献信息

• Corynebactin and a Serine Trilactone Based Analogue:  Chirality and Molecular Modeling of Ferric Complexes
  作者：Martin E. Bluhm、Benjamin P. Hay、Sanggoo S. Kim、Emily A. Dertz、Kenneth N. Raymond

  DOI：10.1021/ic025531y

  日期：2002.10.1

  which has the trilactone ring of enterobactin and the glycine spacer of corynebactin. The chirality and relative conformational stability of the three ferric complexes of enterobactin, corynebactin, and the hybrid have been investigated by molecular modeling (including MM3 and pBP86/DN density functional theory calculations) and circular dichroism spectra. While enterobactin forms a Delta-ferric complex

  由于三价铁离子的水解使其在有氧，接近中性pH的环境中非常不溶，因此大多数细菌会产生铁载体来获取铁（一种基本营养素）。铁铁载体复合物的手性在细胞识别，摄取和利用中起重要作用。从革兰氏阳性细菌中分离出来的棒状杆菌素在结构上与Enterobactin类似，后者首先从革兰氏阴性细菌中分离出来，是众所周知的铁载体，但在三内酯骨架中含有L-苏氨酸而不是L-丝氨酸。棒杆菌素在每个螯合臂中还包含甘氨酸间隔单元。已经制备了具有肠杆菌素的三内酯环和棒杆菌素的甘氨酸间隔基的杂合类似物（丝氨酸-棒杆菌素）。通过分子建模（包括MM3和pBP86 / DN密度泛函理论计算）和圆二色性光谱，研究了肠杆菌素，棒杆菌素和杂合体的三种铁配合物的手性和相对构象稳定性。肠杆菌素形成Delta-铁复​​合物，而棒杆菌素为Lambda。杂合丝氨酸-棒状杆菌素形成近乎外消旋的混合物，而λ-构象异构体稍微过量。每个铁配合物具有四个可能的
• The dhb Operon of Bacillus subtilisEncodes the Biosynthetic Template for the Catecholic Siderophore 2,3-Dihydroxybenzoate-Glycine-Threonine Trimeric Ester Bacillibactin
  作者：Jürgen J. May、Thomas M. Wendrich、Mohamed A. Marahiel

  DOI：10.1074/jbc.m009140200

  日期：2001.3

  Bacillus subtilis was reported to produce the catecholic siderophore itoic acid (2,3-dihydroxybenzoate (DHB)-glycine) in response to iron deprivation, However, by inspecting the DNA sequences of the genes dhbE, dhbB, and dhbF as annotated by the B, subtilis genome project to encode the synthetase complex for the siderophore assembly, various sequence errors within the dhbF gene were predicted and confirmed by re-sequencing. According to the corrected sequence, dhbF encodes a dimodular instead of a monomodular nonribosomal peptide synthetase, We have heterologously expressed, purified, and assayed the substrate selectivity of the recombinant proteins DhbB, DhbE, and DhbF, DhbE, a stand-alone adenylation domain of 59.9 kDa, activates, in an ATP-dependent reaction, I)HB, which is subsequently transferred to the free thiol group of the cofactor phosphopantetheine of the bifunctional isochorismate lyase/aryl carrier protein DhbB, The third synthetase, DhbF, is a dimodular nonribosomal peptide synthetase of 264 kDa that specifically adenylates threonine and, to a lesser extent, glycine and that covalently loads both amino acids onto their corresponding peptidyl carrier domains. To functionally link the dhb gene cluster to siderophore synthesis, we have disrupted the dhbF gene. Comparative mass spectrometric analysis of culture extracts from both the wild type and the dhbF mutant led to the identification of a mass peak at mit 881 ([M-H](1-)) that corresponds to a cyclic trimeric ester of DHB-glycine-threonine.