9-deoxo-31-O-demethyl-FK506 | 181229-32-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯内酰胺
• 英文名称: 9-deoxo-31-O-demethyl-FK506
• 英文别名: 9-deoxo-31-O-demethylFK506；(1S,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(E)-1-[(1R,3R,4R)-3,4-dihydroxycyclohexyl]prop-1-en-2-yl]-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-17-prop-2-enyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-3,10,16-trione
• CAS: 181229-32-3
• 化学式: C₄₃H₆₉NO₁₁
• 分子量: 776.021
• InChiKey: FYYHDEVDDBWQIW-ZMTUURKYSA-N

物化性质

• 沸点：
  873.0±65.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  55
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  9-deoxo-31-O-demethyl-FK506 在 S-腺苷-L-蛋氨酸 、 magnesium sulfate 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 aq. phosphate buffer 为溶剂， 反应 6.0h， 生成 他克莫司
  参考文献：
  名称：

  Characterization of FK506 Biosynthetic Intermediates Involved in Post-PKS Elaboration

  摘要：

  The post-PKS modification steps of FK506 biosynthesis include C9-oxidation. and 31-O-methylation, but the sequence of these reactions and the exact route have remained unclear. This Study details the post-PM modification pathways in FK506 biosynthesis through the identification of all intermediates and in vitro enzymatic reactions of the cytochrome P450 hydroxylase FkbD and the methyltransferase FkbM. These results complete our understanding of post-PKS, Modification steps to FK506 showing the substrate flexibility of two enzymes involved and the existence of two parallel biosynthetic routes to FK506.

  DOI：

  10.1021/np4001224

文献信息

• FK506 DERIVATIVE MAINTAINING NERVE REGENERATION ACTIVITY WITHOUT IMMUNOSUPPRESSIVE ACTIVITY, AND USE THEREOF
  申请人：INTRON BIOTECHNOLOGY CO., LTD

  公开号：US20170216254A1

  公开（公告）日：2017-08-03

  The present invention relates to an FK506 derivative which has reduced immunosuppressive activity but maintains nerve regeneration activity, a preparing method thereof, and a pharmaceutical composition comprising the same for preventing or treating nervous system diseases. A composition comprising 9-deoxo-prolyl-FK506, 31-O-demethyl-FK506, or 9-deoxo-31-O-demethyl-FK506 can promote nerve regeneration and has reduced immunosuppressive activity, thereby reducing side effects in the treatment of nervous system diseases.
• Characterization of FK506 Biosynthetic Intermediates Involved in Post-PKS Elaboration
  作者：Yeon Hee Ban、Pramod B. Shinde、Jae-yeon Hwang、Myoung-Chong Song、Dong Hwan Kim、Si-Kyu Lim、Jae Kyung Sohng、Yeo Joon Yoon

  DOI：10.1021/np4001224

  日期：2013.6.28

  The post-PKS modification steps of FK506 biosynthesis include C9-oxidation. and 31-O-methylation, but the sequence of these reactions and the exact route have remained unclear. This Study details the post-PM modification pathways in FK506 biosynthesis through the identification of all intermediates and in vitro enzymatic reactions of the cytochrome P450 hydroxylase FkbD and the methyltransferase FkbM. These results complete our understanding of post-PKS, Modification steps to FK506 showing the substrate flexibility of two enzymes involved and the existence of two parallel biosynthetic routes to FK506.