7-(3-Methylbut-2-enyl)-l-tryptophan methyl ester | 1049019-48-8

• 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: 7-(3-Methylbut-2-enyl)-l-tryptophan methyl ester
• 英文别名: methyl (2S)-2-amino-3-[7-(3-methylbut-2-enyl)-1H-indol-3-yl]propanoate
• CAS: 1049019-48-8
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: XZOQOMJHICEVIU-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(3-Methylbut-2-enyl)-l-tryptophan methyl ester 、 甲氧基-三氟甲基苯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  A Nonribosomal Peptide Synthetase-Derived Iron(III) Complex from the Pathogenic Fungus Aspergillus fumigatus

  摘要：

  Small molecules (SMs) play central roles as virulence factors of pathogenic fungi and bacteria; however, genomic analyses suggest that the majority of microbial SMs have remained uncharacterized. Based on microarray analysis followed by comparative metabolomics of overexpression/knockout mutants, we identified a tryptophan-derived iron(III)-complex, hexadehydro-astechrome (HAS), as the major product of the cryptic has nonribosomal peptide synthetase (NRPS) gene cluster in the human pathogen Aspergillus fumigatus. Activation of the has cluster created a highly virulent A. fumigatus strain that increased mortality of infected mice. Comparative metabolomics of different mutant strains allowed to propose a pathway for HAS biosynthesis and further revealed cross-talk with another NAPS pathway producing the anticancer fumitremorgins.

  DOI：

  10.1021/ja311145n
• 作为产物：
  描述：

  7-(dimethylallyl)-L-tryptophan 、 三甲基硅烷化重氮甲烷 以 甲醇 、 甲苯 为溶剂， 反应 0.75h， 生成 7-(3-Methylbut-2-enyl)-l-tryptophan methyl ester
  参考文献：
  名称：

  A Nonribosomal Peptide Synthetase-Derived Iron(III) Complex from the Pathogenic Fungus Aspergillus fumigatus

  摘要：

  Small molecules (SMs) play central roles as virulence factors of pathogenic fungi and bacteria; however, genomic analyses suggest that the majority of microbial SMs have remained uncharacterized. Based on microarray analysis followed by comparative metabolomics of overexpression/knockout mutants, we identified a tryptophan-derived iron(III)-complex, hexadehydro-astechrome (HAS), as the major product of the cryptic has nonribosomal peptide synthetase (NRPS) gene cluster in the human pathogen Aspergillus fumigatus. Activation of the has cluster created a highly virulent A. fumigatus strain that increased mortality of infected mice. Comparative metabolomics of different mutant strains allowed to propose a pathway for HAS biosynthesis and further revealed cross-talk with another NAPS pathway producing the anticancer fumitremorgins.

  DOI：

  10.1021/ja311145n

文献信息

• A 7-dimethylallyl tryptophan synthase from a fungal Neosartorya sp.: Biochemical characterization and structural insight into the regioselective prenylation
  作者：Kengo Miyamoto、Fumihiro Ishikawa、Shinya Nakamura、Yutaka Hayashi、Isao Nakanishi、Hideaki Kakeya

  DOI：10.1016/j.bmc.2014.02.031

  日期：2014.4

  A putative 7-dimethylallyl tryptophan synthase (DMATS) gene from a fungal Neosartorya sp. was cloned and overexpressed as a soluble His(6)-fusion protein in Escherichia coli. The enzyme was found to catalyze the prenylation of L-tryptophan at the C7 position of the indole moiety in the presence of dimethylallyl diphosphate; thus, it functions as a 7-DMATS. In this study, we describe the biochemical characterization of 7-DMATS from Neosartorya sp., referred to as 7-DMATS(Neo), and the structural basis of the regioselective prenylation of L-tryptophan at the C7 position by comparison of the three-dimensional structural models of 7-DMATS(Neo) with FgaPT2 (4-DMATS) from Aspergillus fumigatus. (C) 2014 Elsevier Ltd. All rights reserved.