[1-13C]-2-amino-N-bismethylsulfanyl-ethene-3-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.00,0]dec-4-yl)-propan-1-one | 357342-24-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [1-13C]-2-amino-N-bismethylsulfanyl-ethene-3-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.00,0]dec-4-yl)-propan-1-one
• 英文别名: [1-13C]-2-amino-N-bismethylsulfanyl-ethene-3-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.0^0,0]dec-4-yl)-propan-1-one
• CAS: 357342-24-6
• 化学式: C₂₉H₃₉N₃O₃S₃
• 分子量: 574.834
• InChiKey: MXXHCIHTLKIRCV-ZDNQGFJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  82.6
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [1-13C]-2-amino-N-bismethylsulfanyl-ethene-3-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.00,0]dec-4-yl)-propan-1-one 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以87%的产率得到[1-13C]-N-bismethylsulfanyl-ethene-2-(1,1-dimethyl-2-propenyl)-L-tryptophan
  参考文献：
  名称：

  Studies on the biosynthesis of paraherquamide. Construction of the amino acid framework

  摘要：

  It has been previously established in this laboratory that the beta -methyl-beta -hydroxyproline moiety of the potent anthelmintic agent paraherquamide A, is biosynthetically derived from L-isoleucine. The downstream events from L-Ile to paraherquamide A have now been investigated. The synthesis of [1-(13)C]-labeled L-beta -methylproline is described by means of a Hoffman-Loeffler-Freytag reaction sequence from [1-(13)C]-L-Ile. This amino acid is shown to be a direct biosynthetic precursor to paraherquamide A by feeding and incorporation experiments in growing cultures of Penicillum fellutanum. Three tryptophan-containing dipeptides of L-beta -methylproline have been constructed: [(13)C(2)]-2-(l,1-dimethyl-2-propenyl)-L-tryptophanyl-3(S)-methyl-L-proline [(13)C(2)]-3(S)-methyl-L-prolyl-2-(l,1-dimethyl-2-propenyl)-L-tryptophan and [(13)C(2)]-cyclo-2-(l,1-dimethyl-2-propenyl)-L-tryptophan-3(S)-methyl-L-proline. [alpha-(15)N, 1-(13)C]-2-(1,1-Dimethyl-2-propenyl)-L-tryptophan was also prepared but none of these substances were found to serve as biosynthetic precursors to paraherquamide A. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00449-5
• 作为产物：
  描述：

  2-(1,1-dimethylallyl) gramine 、 在 三丁基膦 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以86%的产率得到[1-13C]-2-amino-N-bismethylsulfanyl-ethene-3-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.00,0]dec-4-yl)-propan-1-one
  参考文献：
  名称：

  Studies on the biosynthesis of paraherquamide. Construction of the amino acid framework

  摘要：

  It has been previously established in this laboratory that the beta -methyl-beta -hydroxyproline moiety of the potent anthelmintic agent paraherquamide A, is biosynthetically derived from L-isoleucine. The downstream events from L-Ile to paraherquamide A have now been investigated. The synthesis of [1-(13)C]-labeled L-beta -methylproline is described by means of a Hoffman-Loeffler-Freytag reaction sequence from [1-(13)C]-L-Ile. This amino acid is shown to be a direct biosynthetic precursor to paraherquamide A by feeding and incorporation experiments in growing cultures of Penicillum fellutanum. Three tryptophan-containing dipeptides of L-beta -methylproline have been constructed: [(13)C(2)]-2-(l,1-dimethyl-2-propenyl)-L-tryptophanyl-3(S)-methyl-L-proline [(13)C(2)]-3(S)-methyl-L-prolyl-2-(l,1-dimethyl-2-propenyl)-L-tryptophan and [(13)C(2)]-cyclo-2-(l,1-dimethyl-2-propenyl)-L-tryptophan-3(S)-methyl-L-proline. [alpha-(15)N, 1-(13)C]-2-(1,1-Dimethyl-2-propenyl)-L-tryptophan was also prepared but none of these substances were found to serve as biosynthetic precursors to paraherquamide A. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00449-5