甲基巴豆酰-辅酶 A | 6247-62-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 甲基巴豆酰-辅酶 A
• 中文别名: 甲基巴豆酰-辅酶A
• 英文名称: tigloyl coenzyme A
• 英文别名: tigloyl-CoA；S-(2-methyl-trans-crotonoyl)-coenzyme-A；S-(2-Methyl-trans-crotonoyl)-coenzym-A；2-methylcrotonoyl-CoA；S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (E)-2-methylbut-2-enethioate
• CAS: 6247-62-7
• 化学式: C₂₆H₄₂N₇O₁₇P₃S
• 分子量: 849.643
• InChiKey: PMWATMXOQQZNBX-DKBZLLMOSA-N

物化性质

• 密度：
  1.79±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  54
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  389
• 氢给体数：
  9
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  甲基巴豆酰-辅酶 A 在 B₁₂-dependent radical S-adenosyl-L-methionine enzyme 、 herbicidins cluster contain methyltransferases HbcF 、 herbicidins cluster contain serine hydrolase HbcH 作用下， 以 aq. phosphate buffer 为溶剂， 反应 16.0h， 生成 herbicidin K
  参考文献：
  名称：

  Elucidation of the Herbicidin Tailoring Pathway Offers Insights into Its Structural Diversity

  摘要：

  The biosynthetic gene clusters for herbicidins (hbc) and aureonuclemycin (anm) were identified in Streptomyces sp. KIB-027 and Streptomyces aureus, respectively. The roles of genes possibly involved in post-core-assembly steps in herbicidin biosynthesis in these clusters and a related her cluster were studied. Through systematic gene deletions, structural elucidation of the accumulated intermediates in the mutants, and in vitro verification of the encoded enzymes, the peripheral modification pathway for herbicidin biosynthesis is now fully established.

  DOI：

  10.1021/acs.orglett.9b00066
• 作为产物：
  描述：

  惕格酸 、 coenzyme A 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.5h， 生成 甲基巴豆酰-辅酶 A
  参考文献：
  名称：

  Elucidation of the Herbicidin Tailoring Pathway Offers Insights into Its Structural Diversity

  摘要：

  The biosynthetic gene clusters for herbicidins (hbc) and aureonuclemycin (anm) were identified in Streptomyces sp. KIB-027 and Streptomyces aureus, respectively. The roles of genes possibly involved in post-core-assembly steps in herbicidin biosynthesis in these clusters and a related her cluster were studied. Through systematic gene deletions, structural elucidation of the accumulated intermediates in the mutants, and in vitro verification of the encoded enzymes, the peripheral modification pathway for herbicidin biosynthesis is now fully established.

  DOI：

  10.1021/acs.orglett.9b00066

文献信息

• Discovery and Engineering of Pathways for Production of α-Branched Organic Acids
  作者：Michael R. Blaisse、Hongjun Dong、Beverly Fu、Michelle C. Y. Chang

  DOI：10.1021/jacs.7b07400

  日期：2017.10.18

  branch using a propionyl-CoA extender unit. Engineering synthetic pathways for production of α-methyl acids in Escherichia coli using these enzymes allows the construction of microbial strains that produce either chiral 2-methyl-3-hydroxy acids (1.1 ± 0.2 g L-1) or branched enoic acids (1.12 ± 0.06 g L-1) in the presence of a dehydratase at 44% and 87% yield of fed propionate, respectively. In vitro characterization

  基于细胞的合成为从简单的可再生碳源制备小分子提供了许多机会，通过将多个反应伸缩到一个发酵步骤中。该领域的一个挑战是开发酶促碳-碳键形成循环，使目标结构模块化断开为细胞构建块。在这方面，基于硫解酶催化酰基辅酶 A (CoA) 底物之间初始碳-碳键形成步骤的合成途径为生物合成提供了通用途径，但目前此类途径的底物多样性有限。在本报告中，我们描述了参与蛔虫蛔虫中分支酸产生的硫解酶-酮还原酶对的鉴定和生化表征，这证明了使用丙酰辅酶 A 扩展单元形成具有 α-甲基支链的产物的选择性。使用这些酶在大肠杆菌中设计用于生产 α-甲基酸的工程合成途径，可以构建生产手性 2-甲基-3-羟基酸 (1.1 ± 0.2 g L-1) 或支链烯酸 (1.12 ± 0.06 g L-1) 在脱水酶的存在下，进料丙酸盐的产率分别为 44% 和 87%。体外表征和体内分析表明，酮还原酶是选择性的关键驱动因素，即使与高度偏爱无
• Wieland; Rueff, Angewandte Chemie, 1953, vol. 65, p. 186
  作者：Wieland、Rueff

  DOI：——

  日期：——
• Robinson et al., Journal of Biological Chemistry, 1956, vol. 218, p. 391,398
  作者：Robinson et al.

  DOI：——

  日期：——
• Elucidation of the Herbicidin Tailoring Pathway Offers Insights into Its Structural Diversity
  作者：Hai-Xue Pan、Zhang Chen、Tianfang Zeng、Wen-Bing Jin、Yujie Geng、Geng-Min Lin、Juan Zhao、Wei-Tao Li、Zijun Xiong、Sheng-Xiong Huang、Xin Zhai、Hung-wen Liu、Gong-Li Tang

  DOI：10.1021/acs.orglett.9b00066

  日期：2019.3.1

  The biosynthetic gene clusters for herbicidins (hbc) and aureonuclemycin (anm) were identified in Streptomyces sp. KIB-027 and Streptomyces aureus, respectively. The roles of genes possibly involved in post-core-assembly steps in herbicidin biosynthesis in these clusters and a related her cluster were studied. Through systematic gene deletions, structural elucidation of the accumulated intermediates in the mutants, and in vitro verification of the encoded enzymes, the peripheral modification pathway for herbicidin biosynthesis is now fully established.