3-Dimethylallyl-l-tyrosine | 1075238-13-9

• 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: 3-Dimethylallyl-l-tyrosine
• 英文别名: (2S)-2-amino-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]propanoic acid
• CAS: 1075238-13-9
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: UFFPHPAGEHMRFF-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基丁-2-烯基膦酰磷酸氢酯 、 L-酪氨酸 在 tryptophan prenyltransferase FgaPT₂ from Aspergillus fumigatus 、 calcium chloride 作用下， 以 二甲基亚砜 、 甘油 为溶剂， 反应 1.5h， 以6.2%的产率得到3-Dimethylallyl-l-tyrosine
  参考文献：
  名称：

  Tryptophan prenyltransferases showing higher catalytic activities for Friedel–Crafts alkylation of o- and m-tyrosines than tyrosine prenyltransferases

  摘要：

  通过色氨酸侧链烯基转移酶（Trp-PTs）更好地将酪氨酸（l-o-和l-m-酪氨酸）转化为它们的烯基化衍生物，胜过酪氨酸O-烯基转移酶（Tyr-O-PT）。

  DOI：

  10.1039/c5ob01040c

文献信息

• SYNTHESIS OF (S)-2-ACETAMIDO-3-(4-HYDROXY-3-(3-METHYLBUT-2-ENYL) PHENYL) PROPANOIC ACID DERIVATIVES
  申请人：King Fahd University of Petroleum and Minerals

  公开号：US20170114004A1

  公开（公告）日：2017-04-27

  A method for producing a compound of formula (I) or a pharmaceutically acceptable salt, solvate, tautomer or stereoisomer, such as compound 1 and compound 2 is disclosed. The method proceeds through an O-allylated tyrosine-based compound, such as compound 3 and preferably comprises [3,3] sigmatropic Claisen rearrangement and olefin cross metathesis reactions. In addition, a pharmaceutical composition comprising a compound of formula (I) a tumor necrosis factor (TNF) related apoptosis inducing ligand (TRAIL) and a pharmaceutically acceptable carrier or excipient is disclosed.

  本发明公开了一种制备式(I)化合物或其药学上可接受的盐、溶剂化物、互变异构体或立体异构体的方法，例如化合物1和化合物2。该方法通过一种O-烯丙基化的基于酪氨酸的化合物，例如化合物3进行，最好包括[3,3]sigmatropic Claisen重排和烯烃交叉重聚反应。此外，本发明还公开了一种包含式(I)化合物、肿瘤坏死因子(TNF)相关的凋亡诱导配体(TRAIL)和药学上可接受的载体或赋形剂的制药组合物。
• Uncatalyzed sigmatropic rearrangement of tyrosine-based compounds
  申请人：King Fahd University of Petroleum and Minerals

  公开号：US10023527B2

  公开（公告）日：2018-07-17

  A method for producing a compound of formula (I) or a pharmaceutically acceptable salt, solvate, tautomer or stereoisomer, such as compound 1 and compound 2 is disclosed. The method proceeds through an O-allylated tyrosine-based compound, such as compound 3 and preferably comprises [3,3] sigmatropic Claisen rearrangement and olefin cross metathesis reactions. In addition, a pharmaceutical composition comprising a compound of formula (I) a tumor necrosis factor (TNF) related apoptosis inducing ligand (TRAIL) and a pharmaceutically acceptable carrier or excipient is disclosed.

  本发明公开了一种生产式（I）化合物或药学上可接受的盐、溶液剂、同分异构体或立体异构体（如化合物 1 和化合物 2）的方法。该方法通过 O-烯丙基化的酪氨酸基化合物（如化合物 3）进行，最好包括 [3,3] sigmatropic Claisen 重排和烯烃交叉偏析反应。此外，还公开了一种药物组合物，该组合物包含式（I）化合物、肿瘤坏死因子（TNF）相关凋亡诱导配体（TRAIL）和药学上可接受的载体或赋形剂。
• Method for making a prenyl group-substituted tyrosine compound
  申请人：King Fahd University of Petroleum and Minerals

  公开号：US10329245B2

  公开（公告）日：2019-06-25

  A method for producing a compound of formula (I) or a pharmaceutically acceptable salt, solvate, tautomer or stereoisomer, such as compound 1 and compound 2 is disclosed. The method proceeds through an O-allylated tyrosine-based compound, such as compound 3 and preferably comprises [3,3] sigmatropic Claisen rearrangement and olefin cross metathesis reactions. In addition, a pharmaceutical composition comprising a compound of formula (I) a tumor necrosis factor (TNF) related apoptosis inducing ligand (TRAIL) and a pharmaceutically acceptable carrier or excipient is disclosed.

  本发明公开了一种生产式（I）化合物或药学上可接受的盐、溶液剂、同分异构体或立体异构体（如化合物 1 和化合物 2）的方法。该方法通过 O-烯丙基化的酪氨酸基化合物（如化合物 3）进行，最好包括 [3,3] sigmatropic Claisen 重排和烯烃交叉偏析反应。此外，还公开了一种药物组合物，该组合物包含式（I）化合物、肿瘤坏死因子（TNF）相关凋亡诱导配体（TRAIL）和药学上可接受的载体或赋形剂。
• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。
• Site-directed Mutagenesis Switching a Dimethylallyl Tryptophan Synthase to a Specific Tyrosine C3-Prenylating Enzyme
  作者：Aili Fan、Georg Zocher、Edyta Stec、Thilo Stehle、Shu-Ming Li

  DOI：10.1074/jbc.m114.623413

  日期：2015.1

  The tryptophan prenyltransferases FgaPT2 and 7-DMATS (7-dimethylallyl tryptophan synthase) from Aspergillus fumigatus catalyze C-4- and C-7-prenylation of the indole ring, respectively. 7-DMATS was found to accept L-tyrosine as substrate as well and converted it to an O-prenylated derivative. An acceptance of L-tyrosine by FgaPT2 was also observed in this study. Interestingly, isolation and structure elucidation revealed the identification of a C-3-prenylated L-tyrosine as enzyme product. Molecular modeling and site-directed mutagenesis led to creation of a mutant FgaPT2_K174F, which showed much higher specificity toward L-tyrosine than L-tryptophan. Its catalytic efficiency toward L-tyrosine was found to be 4.9-fold in comparison with that of non-mutated FgaPT2, whereas the activity toward L-tryptophan was less than 0.4% of that of the wild-type. To the best of our knowledge, this is the first report on an enzymatic C-prenylation of L-tyrosine as free amino acid and altering the substrate preference of a prenyltransferase by mutagenesis.