除莠菌素 A | 55353-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 除莠菌素 A
• 中文别名: 除莠菌素A
• 英文名称: herbicidin A
• 英文别名: methyl (1R,3S,4R,5R,7R,9R,11S,12S,13S)-5-(6-aminopurin-9-yl)-1,12-dihydroxy-13-[(E)-2-(hydroxymethyl)but-2-enoyl]oxy-4-methoxy-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate
• CAS: 55353-31-6
• 化学式: C₂₃H₂₉N₅O₁₁
• 分子量: 551.51
• InChiKey: LOWKANMKNQBRPJ-MRAUHCMASA-N

物化性质

• 沸点：
  826.5±75.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：可溶； DMSO：可溶；乙醇：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  220
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  除莠菌素 A 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：

  甲醇 、 herbicidin H 在 B₁₂-dependent radical S-adenosyl-L-methionine enzyme 、 herbicidins cluster contain methyltransferases HbcG 作用下， 以 aq. phosphate buffer 为溶剂， 反应 8.0h， 生成 除莠菌素 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

• Identification and Interrogation of the Herbicidin Biosynthetic Gene Cluster: First Insight into the Biosynthesis of a Rare Undecose Nucleoside Antibiotic
  作者：Geng-Min Lin、Anthony J. Romo、Priscilla H. Liem、Zhang Chen、Hung-wen Liu

  DOI：10.1021/jacs.7b08985

  日期：2017.11.22

  l-isoleucine catabolism. Identification of the gene cluster for herbicidin A biosynthesis in Streptomyces sp. L-9-10 as well as its verification by heterologous expression in a nonproducing host are described, and the results of in vitro characterization of a carboxyl methyltransferase encoded in the cluster, Her8, are presented. Based on these observations, a biosynthetic pathway is proposed for herbicidins

  除草素是基于腺苷的核苷类抗生素，具有一个不寻常的三环十一碳核，并饰有（5-羟基）烯丙基部分。本文报道了进食研究，证明三环核心衍生自d-葡萄糖和d-核糖，而tiglyl部分衍生自1-异亮氨酸分解代谢的中间体。链霉菌中除草素A生物​​合成基因簇的鉴定。描述了L-9-10及其在非生产性宿主中通过异源表达进行的验证，以及体外结果介绍了在簇Her8中编码的羧基甲基转移酶的特征。基于这些观察，提出了除草剂的生物合成途径。
• 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.