(-)-teleocidin B-1 | 11032-05-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-teleocidin B-1
• 英文别名: teleocidin B-1；teleocidin B1；(6S,9S,14S,17R)-17-ethenyl-6-(hydroxymethyl)-10,14,17-trimethyl-9,14-di(propan-2-yl)-2,7,10-triazatetracyclo[9.7.1.04,19.013,18]nonadeca-1(18),3,11(19),12-tetraen-8-one
• CAS: 11032-05-6；95044-71-6；95189-05-2；95189-06-3；114247-84-6；114247-88-0；123539-25-3；123539-26-4
• 化学式: C₂₈H₄₁N₃O₂
• 分子量: 451.652
• InChiKey: PEYTUVXFLCCGCC-VCJXGGRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  68.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  olivoretin B 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 (-)-teleocidin B-1
  参考文献：
  名称：

  Isolation and structure elucidation of teleocidin B-1, B-2, B-3, and B-4.

  摘要：

  From the mycelia of Streptomyces mediocidicus four metabolites teleocidin B-1, B-2, B-3 and B-4 were isolated in crystalline states and their structures were determined by comparison with the known des-O-methylolivoretin B, and olivoretin D (teleocidin B of Hirata), and by studying the 13C-nuclear magnetic resonance (NMR) spectra.

  DOI：

  10.1248/cpb.32.4233

文献信息

• 11-Step Total Synthesis of Teleocidins B-1–B-4
  作者：Hugh Nakamura、Kosuke Yasui、Yuzuru Kanda、Phil S. Baran

  DOI：10.1021/jacs.8b13697

  日期：2019.1.30

  A unified and modular approach to the teleocidin B family of natural products is presented that proceeds in 11 steps and features an array of interesting strategies and methods. Indolactam V, the known biosynthetic precursor to this family, was accessed through electrochemical amination, Cu-mediated aziridine opening, and a remarkable base-induced macrolactamization. Guided by a desire to minimize

  提出了一种针对天然产物 Teleocidin B 家族的统一和模块化方法，该方法分 11 个步骤进行，并具有一系列有趣的策略和方法。Indolactam V 是该家族已知的生物合成前体，通过电化学胺化、Cu 介导的氮丙啶开放和显着的碱诱导大环内酰胺化获得。在最小化让步步骤的愿望的指导下，CH 硼酸化和 Sigman-Heck 变换的战术组合使 Teleocidins 的聚合、立体控制合成成为可能。
• Crystal structure and enantioselectivity of terpene cyclization in SAM-dependent methyltransferase TleD
  作者：Feng Yu、Minjun Li、Chunyan Xu、Bo Sun、Huan Zhou、Zhijun Wang、Qin Xu、Muyun Xie、Gang Zuo、Pei Huang、Haojie Guo、Qisheng Wang、Jianhua He

  DOI：10.1042/bcj20160695

  日期：2016.12.1

  biosynthesis pathway. Besides methyl transferring, TleD also rearranges the geranyl and indole moieties of the precursor to form a six-membered ring. Moreover, it does not show homologies with any known terpenoid cyclases. In order to elucidate how such a remarkable reaction could be achieved, we determined the complex crystal structures of TleD and the cofactor analogue S-adenosyl-l-homocysteine with

  TleD是依赖于SAM（S-腺苷-1-蛋氨酸）的甲基转移酶，它是Teleocidin B生物合成途径中的关键酶之一。除甲基转移外，TleD还重排前体的香叶基和吲哚基以形成六元环。而且，它没有显示出与任何已知的萜类环化酶的同源性。为了阐明如何实现如此显着的反应，我们确定了TleD和辅因子类似物S-腺苷-1-同型半胱氨酸的复杂晶体结构，有或没有底物衔铁抑制素A1。在TleD六聚体中观察到通过其他N端α-螺旋的结构域交换模式。结构比较和比对表明，这种额外的N末端α-螺旋是SAM甲基转移酶样环化酶TleD和SpnF的共同特征。Tyr21残基将额外的N末端α-螺旋锚固到“核心SAM-MT折叠”，并且是催化活性的关键残基。分子动力学模拟结果表明，在TleD和底物复杂的结构中，teleoocidin A1的二面角C23-C24-C25-C26比60-90°更可取，反应后在C25位置倾向于采用Re-fac
• Isolation and structure elucidation of teleocidin B-1, B-2, B-3, and B-4.
  作者：Yukio Hitotsuyanagi、Hirota Fujiki、Masami Suganuma、Norio Aimi、Shinichiro Sakai、Yasuyuki Endo、Koichi Shudo、Takashi Sugimura

  DOI：10.1248/cpb.32.4233

  日期：——

  From the mycelia of Streptomyces mediocidicus four metabolites teleocidin B-1, B-2, B-3 and B-4 were isolated in crystalline states and their structures were determined by comparison with the known des-O-methylolivoretin B, and olivoretin D (teleocidin B of Hirata), and by studying the 13C-nuclear magnetic resonance (NMR) spectra.