6-methylpretetramide | 2602-31-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 四环素类
• 英文名称: 6-methylpretetramide
• 英文别名: 6-methylpretetramid；1,3,10,11,12-pentahydroxy-6-methyl-naphthacene-2-carboxylic acid amide；1,3,10,11,12-Pentahydroxy-6-methyl-naphthacen-2-carbonsaeure-amid；1,3,10,11,12-Pentahydroxy-6-methyl-naphthacen-carboxamid-(2)；Dedimethylamino-terrarubein；6-Methyl-praetetramid；1,3,10,11,12-Pentahydroxy-6-methyltetracene-2-carboxamide
• CAS: 2602-31-5
• 化学式: C₂₀H₁₅NO₆
• 分子量: 365.342
• InChiKey: WBDQDVXPSGTJAV-UHFFFAOYSA-N

物化性质

• 沸点：
  817.2±65.0 °C(Predicted)
• 密度：
  1.668±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  144
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-methylpretetramide 在 DL-dithiothreitol 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 phosphate buffer 、 二甲基亚砜 为溶剂， 生成 5a.6-Anhydro-4-oxo-tetracyclin
  参考文献：
  名称：

  Identifying the Minimal Enzymes Required for Anhydrotetracycline Biosynthesis

  摘要：

  The cyclohexenone ring A of tetracyclines exhibits unique structural features not observed among other aromatic polyketides. These substitutions include the C2 primary amide, C4 dimethylamine, and the C12a tertiary alcohol. Here we report the identification and reconstitution of the minimum set of enzymes required for the biosynthesis of anhydrotetracycline (ATC, 5), the first intermediate in the tetracycline biosynthetic pathway that contains the fully functionalized ring A. Using a combination of in vivo and in vitro approaches, we confirmed OxyL, OxyQ, and OxyT to be the only enzymes required to convert 6-methylpretetramid 1 into 5. OxyL is a NADPH-dependent dioxygenase that introduces two oxygen atoms into 1 to yield the unstable intermediate 4-keto-ATC 2. The aminotransferase OxyQ catalyzes the reductive amination of C4-keto of 2, yielding 4-amino-ATC 3. Furthermore, the N,N-dimethyltransferase OxyT catalyzes the formation of 5 from 3 in a (S)-adenosylmethionine (SAM)-dependent manner. Finally, a "non-natural" anhydrotetracycline derivative was generated, demonstrating that our heterologous host/vector pair can be a useful platform toward the engineered biosynthesis of tetracycline analogues.

  DOI：

  10.1021/ja800951e
• 作为产物：
  描述：

  4-dedimethylamino-12a-deoxyterramycin 在 盐酸 作用下， 生成 6-methylpretetramide
  参考文献：
  名称：

  The Structure of Terramycin^1,2

  摘要：

  DOI：

  10.1021/ja01118a001

文献信息

• Tetracycline studies. Part III. Trimethylsilyl derivatives of tetracyclines
  作者：C. H. Hassall、G. J. Thomas

  DOI：10.1039/j39700000636

  日期：——

  Tetracyclines, and ring A models, are converted by trimethylchlorosilane and hexamethyldisilazane in pyridine into trimethylsilyl derivatives which dissolve readily in common solvents. This has facilitated the use of n.m.r. and i.r. spectra in elucidating the molecular structures of tetracyclines.

  四环素和A环模型在吡啶中被三甲基氯硅烷和六甲基二硅氮烷转化为三甲基甲硅烷基衍生物，该衍生物易于溶解在普通溶剂中。这有助于使用nmr和ir光谱阐明四环素的分子结构。
• Biomimetic syntheses of pretetramides. 3. Synthesis of 6-methylpretetramides using a preassembled D ring template
  作者：Thomas M. Harris、Constance M. Harris、Peter C. Kuzma、John Y. C. Lee、Sankaran. Mahalingam、S. Gordon. Gilbreath

  DOI：10.1021/ja00226a038

  日期：1988.8
• Synthesis of 6-methylpretetramid, the fully aromatic precursor of tetracycline
  作者：S. Mahalingam、Peter C. Kuzma、John Y. C. Lee、Thomas M. Harris

  DOI：10.1021/ja00311a088

  日期：1985.12
• HARRIS, THOMAS M.;HARRIS, CONSTANCE M.;KUZMA, PETER C.;LEE, JOHN Y. -C.;-+, J. AMER. CHEM. SOC., 110,(1988) N 18, C. 6183-6192
  作者：HARRIS, THOMAS M.、HARRIS, CONSTANCE M.、KUZMA, PETER C.、LEE, JOHN Y. -C.、-+

  DOI：——

  日期：——
• The Structure of Terramycin^1,2
  作者：F. A. Hochstein、C. R. Stephens、L. H. Conover、P. P. Regna、R. Pasternack、P. N. Gordon、F. J. Pilgrim、K. J. Brunings、R. B. Woodward

  DOI：10.1021/ja01118a001

  日期：1953.11