herbicidin K | 1569269-02-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: herbicidin K
• 英文别名: 2'-O-demethylherbicidin F；methyl (1R,3R,4R,5R,7R,9R,11S,12S,13S)-5-(6-aminopurin-9-yl)-1,4,12-trihydroxy-13-[(E)-2-methylbut-2-enoyl]oxy-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate
• CAS: 1569269-02-8
• 化学式: C₂₂H₂₇N₅O₁₀
• 分子量: 521.484
• InChiKey: LUHFPLRYWUPHKS-ORBSYVJISA-N

物化性质

• 沸点：
  818.1±75.0 °C(Predicted)
• 密度：
  1.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  211
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  herbicidin K 在 coenzyme A 、 B₁₂-dependent radical S-adenosyl-L-methionine enzyme 、 herbicidins cluster contain methyltransferases HbcG 、 herbicidins cluster contain serine hydrolase HbcH 作用下， 以 aq. phosphate buffer 为溶剂， 反应 16.0h， 生成 除莠菌素 B
  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：

  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

文献信息

• 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.