herbicidin C | 72067-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: herbicidin C
• 英文别名: methyl (1S,3R,4R,5R,7R,9R,11S,12S,13S)-5-(6-aminopurin-9-yl)-1,4,12,13-tetrahydroxy-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate
• CAS: 72067-14-2
• 化学式: C₁₇H₂₁N₅O₉
• 分子量: 439.382
• InChiKey: OEWSVQOLWMAJBV-PRSVBILDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  205
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  herbicidin C 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以33%的产率得到aureonuclemycin
  参考文献：
  名称：

  通过后期糖基化的立体选择总合成的除草素C和金霉素。

  摘要：

  迟到总比不到好！首次合成了两个重要的核苷类抗生素成员的除草素。该路线将立体选择性C-糖基化与几种试剂控制的立体选择性转化以及令人惊讶的简便且高度非对映选择性的后期N-糖基化结合在一起。

  DOI：

  10.1002/anie.201201826
• 作为产物：
  描述：

  herbicidin K 在 B₁₂-dependent radical S-adenosyl-L-methionine enzyme 、 herbicidins cluster contain methyltransferases HbcF 、 水 、 lithium hydroxide 作用下， 以 aq. phosphate buffer 为溶剂， 反应 11.0h， 生成 herbicidin C
  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

• Stereoselective Total Syntheses of Herbicidin C and Aureonuclemycin through Late-Stage Glycosylation
  作者：Dominik Hager、Peter Mayer、Christian Paulitz、Jörg Tiebes、Dirk Trauner

  DOI：10.1002/anie.201201826

  日期：2012.6.25

  Better late than never! Two herbicidins, members of an important family of nucleoside antibiotics, have been synthesized for the first time. The route integrates a stereoselective C‐glycosylation with several reagent‐controlled stereoselective transformations and a surprisingly facile and highly diastereoselective late‐stage N‐glycosylation.

  迟到总比不到好！首次合成了两个重要的核苷类抗生素成员的除草素。该路线将立体选择性C-糖基化与几种试剂控制的立体选择性转化以及令人惊讶的简便且高度非对映选择性的后期N-糖基化结合在一起。
• 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.
• Total Synthesis of Herbicidin C and Aureonuclemycin: Impasses and New Avenues
  作者：Dominik Hager、Christian Paulitz、Jörg Tiebes、Peter Mayer、Dirk Trauner

  DOI：10.1021/jo401706r

  日期：2013.11.1

  The undecose nucleoside antibiotics herbicidin C and aureonuclemycin are biologically highly active and represent challenging targets for total synthesis. Herein, the gradual evolution of our synthetic strategy toward these natural products is described in detail. The initial route encompasses metalate addition chemistry but suffers from poor stereochemical control. In contrast, the ultimately successful

  十一糖核苷抗生素除草素C和金黄色葡萄球菌素具有很高的生物活性，是全合成的具有挑战性的目标。在此，详细描述了我们对这些天然产物的合成策略的逐步发展。最初的途径包括金属盐加成化学，但立体化学控制不佳。相反，最终成功的策略得益于各种试剂控制的立体选择性转化，包括出乎意料的简便且高度非对映选择性的N-糖基化过程。提出的工作还描述了可能在碳水化合物化学中找到进一步应用的新组成部分。