[1-13C]-2-(1,1-dimethyl-2-propenyl)-L-tryptophan | 357342-27-9

• 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: [1-13C]-2-(1,1-dimethyl-2-propenyl)-L-tryptophan
• 英文别名: (2S)-2-amino-3-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl](113C)propanoic acid
• CAS: 357342-27-9
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 273.336
• InChiKey: XOWJLZPKXHOSPF-XXOGGYJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1-13C]-2-(1,1-dimethyl-2-propenyl)-L-tryptophan 在 lithium hydroxide 、 3 A molecular sieve 、 camphor-10-sulfonic acid 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 76.0h， 生成 [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：

  2-(1,1-dimethylallyl) gramine 在 盐酸 、 lithium hydroxide 、 三丁基膦 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 56.0h， 生成 [1-13C]-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

文献信息

• Studies on the biosynthesis of paraherquamide. Construction of the amino acid framework
  作者：Emily M Stocking、Juan F Sanz-Cervera、Clifford J Unkefer、Robert M Williams

  DOI：10.1016/s0040-4020(01)00449-5

  日期：2001.6

  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.