(R)-[1-(2)H]brassinin | 1287305-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-[1-(2)H]brassinin
• 英文别名: (R)-[1'-2H]Brassinin；methyl N-[(R)-deuterio(1H-indol-3-yl)methyl]carbamodithioate
• CAS: 1287305-37-6
• 化学式: C₁₁H₁₂N₂S₂
• 分子量: 237.354
• InChiKey: QYKQWFZDEDFELK-ZVGOLAHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-[1-(2)H]brassinin 在 L-1,4-二硫代苏糖醇 、 Leptosphaeria maculans brassinin oxidase 、 水 、 5-甲基吩嗪硫酸甲酯 、 二乙醇胺 作用下， 生成 3-吲哚甲醛
  参考文献：
  名称：

  Brassinin oxidase mediated transformation of the phytoalexin brassinin: Structure of the elusive co-product, deuterium isotope effect and stereoselectivity

  摘要：

  Brassinin oxidase, a fungal detoxifying enzyme that mediates the conversion of the phytoalexin brassinin into indole-3-carboxaldehyde, is the first enzyme described to date that catalyzes the transformation of a dithiocarbamate group into an aldehyde equivalent. Brassinin is an essential phytoalexin due to its antifungal activity and its role as biosynthetic precursor of other phytoalexins produced in plants of the family Brassicaceae (common name crucifer). In this report, the isolation, structure determination and synthesis of the elusive co-product of brassinin transformation by brassinin oxidase, S-methyl dithiocarbamate, the syntheses of dideuterated and (R) and (S) monodeuterated brassinins, kinetic analyses of isotope effects and chemical modifications of brassinin oxidase are described. The reaction of [1'-H-2(2)] brassinin was found to be slowed by a kinetic isotope effect of 5.3 on the value of k(cat)/K-m. This result indicates that the hydride/hydrogen transfer step preceding brassinin transformation is rate determining in the overall reaction. In addition, the use of (R) and (S)-[1'-H-2] brassinins as substrates indicated that the hydride/hydrogen transfer step is ca. 88% stereoselective for the pro-R hydrogen. A detailed chemical mechanism of the enzymatic transformation of brassinin is proposed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.011

文献信息

• Brassinin oxidase mediated transformation of the phytoalexin brassinin: Structure of the elusive co-product, deuterium isotope effect and stereoselectivity
  作者：M. Soledade C. Pedras、Zoran Minic、Vijay K. Sarma-Mamillapalle

  DOI：10.1016/j.bmc.2011.01.011

  日期：2011.2

  Brassinin oxidase, a fungal detoxifying enzyme that mediates the conversion of the phytoalexin brassinin into indole-3-carboxaldehyde, is the first enzyme described to date that catalyzes the transformation of a dithiocarbamate group into an aldehyde equivalent. Brassinin is an essential phytoalexin due to its antifungal activity and its role as biosynthetic precursor of other phytoalexins produced in plants of the family Brassicaceae (common name crucifer). In this report, the isolation, structure determination and synthesis of the elusive co-product of brassinin transformation by brassinin oxidase, S-methyl dithiocarbamate, the syntheses of dideuterated and (R) and (S) monodeuterated brassinins, kinetic analyses of isotope effects and chemical modifications of brassinin oxidase are described. The reaction of [1'-H-2(2)] brassinin was found to be slowed by a kinetic isotope effect of 5.3 on the value of k(cat)/K-m. This result indicates that the hydride/hydrogen transfer step preceding brassinin transformation is rate determining in the overall reaction. In addition, the use of (R) and (S)-[1'-H-2] brassinins as substrates indicated that the hydride/hydrogen transfer step is ca. 88% stereoselective for the pro-R hydrogen. A detailed chemical mechanism of the enzymatic transformation of brassinin is proposed. (C) 2011 Elsevier Ltd. All rights reserved.