6-(2-trans-pentenyl)-L-tryptophan | 1398242-63-1

• 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: 6-(2-trans-pentenyl)-L-tryptophan
• 英文别名: 6-(2-trans-pentenyl)-L-Trp；(2S)-2-amino-3-[6-[(E)-pent-2-enyl]-1H-indol-3-yl]propanoic acid
• CAS: 1398242-63-1
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: IFYMNUSIUCRNPS-XGACYXMMSA-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：
  6
• 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

• 作为产物：
  描述：

  2-trans-pentenyl diphosphate 、 L-色氨酸 在 5-dimethylallyltryptophan synthase 、 二甲基亚砜 、 甘油 、 calcium chloride 作用下， 以 水 为溶剂， 反应 65745.0h， 以91%的产率得到6-(2-trans-pentenyl)-L-tryptophan
  参考文献：
  名称：

  Expansion of Enzymatic Friedel–Crafts Alkylation on Indoles: Acceptance of Unnatural β-Unsaturated Allyl Diphospates by Dimethylallyl-tryptophan Synthases

  摘要：

  Prenyltransferases of the dimethylallyl-tryptophan synthase (DMATS) superfamily catalyze Friedel-Crafts alkylation with high flexibility for aromatic substrates, but the high specificity for dimethylallyl diphosphate (DMAPP) prohibits their application as biocatalysts. We demonstrate here that at least one methyl group in DMAPP can be deleted or shifted to the delta-position. For acceptance by some DMATS enzymes, however, a double bond must be situated at the beta-position. Furthermore, the alkylation position of an analogue can differ from that of DMAPP.

  DOI：

  10.1021/ol302207r

文献信息

• Expansion of Enzymatic Friedel–Crafts Alkylation on Indoles: Acceptance of Unnatural β-Unsaturated Allyl Diphospates by Dimethylallyl-tryptophan Synthases
  作者：Mike Liebhold、Xiulan Xie、Shu-Ming Li

  DOI：10.1021/ol302207r

  日期：2012.9.21

  Prenyltransferases of the dimethylallyl-tryptophan synthase (DMATS) superfamily catalyze Friedel-Crafts alkylation with high flexibility for aromatic substrates, but the high specificity for dimethylallyl diphosphate (DMAPP) prohibits their application as biocatalysts. We demonstrate here that at least one methyl group in DMAPP can be deleted or shifted to the delta-position. For acceptance by some DMATS enzymes, however, a double bond must be situated at the beta-position. Furthermore, the alkylation position of an analogue can differ from that of DMAPP.