[13C2]-N-bismethylsulfanyl-ethene-2-(1,1-dimethyl-2-propenyl)-L-tryptophanyl-3(S)-methyl-L-proline ethyl ester | 357342-26-8

• 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: [13C2]-N-bismethylsulfanyl-ethene-2-(1,1-dimethyl-2-propenyl)-L-tryptophanyl-3(S)-methyl-L-proline ethyl ester
• CAS: 357342-26-8
• 化学式: C₂₇H₃₇N₃O₃S₂
• 分子量: 517.719
• InChiKey: RLAUZFLAUIEIEY-LLKXSDQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  74.76
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [13C2]-N-bismethylsulfanyl-ethene-2-(1,1-dimethyl-2-propenyl)-L-tryptophanyl-3(S)-methyl-L-proline ethyl ester 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以100%的产率得到[13C2]-2-(1,1-dimethyl-2-propenyl)-L-tryptophanyl-3(S)-methyl-L-proline
  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：

  在 lithium hydroxide 、 三丁基膦 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 35.5h， 生成 [13C2]-N-bismethylsulfanyl-ethene-2-(1,1-dimethyl-2-propenyl)-L-tryptophanyl-3(S)-methyl-L-proline ethyl ester
  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