(R)-2-amino-3-(4-methyl-1H-indol-3-yl)propanoic acid

• 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: (R)-2-amino-3-(4-methyl-1H-indol-3-yl)propanoic acid
• 英文别名: (2R)-2-amino-3-(4-methyl-1H-indol-3-yl)propanoic acid
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: FPJGLSZLQLNZIW-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲基-DL-色氨酸 在 IvoA acetyltransferase 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 aq. phosphate buffer 为溶剂， 反应 12.0h， 以99%的产率得到
  参考文献：
  名称：

  Complete Stereoinversion of l-Tryptophan by a Fungal Single-Module Nonribosomal Peptide Synthetase

  摘要：

  Single-module nonribosomal peptide synthetases (NRPSs) and NRPS-like enzymes activate and transform carboxylic acids in both primary and secondary metabolism and are of great interest due to their biocatalytic potentials. The single-module NRPS IvoA is essential for fungal pigment biosynthesis. Here, we show that IvoA catalyzes ATP-dependent unidirectional stereo inversion of L-tryptophan to D-tryptophan with complete conversion. While the stereoinversion is catalyzed by the epimerization (E) domain, the terminal condensation (C) domain stereoselectively hydrolyzes D-tryptophanyl-S-phosphopantetheine thioester and thus represents a noncanonical C domain function. Using IvoA, we demonstrate a biocatalytic stereoinversion/deracemization route to access a variety of substituted D-tryptophan analogs in high enantiomeric excess.

  DOI：

  10.1021/jacs.9b08898

文献信息

• One-Pot Biocatalytic Synthesis of Substituted<scp>d</scp>-Tryptophans from Indoles Enabled by an Engineered Aminotransferase
  作者：Fabio Parmeggiani、Arnau Rué Casamajo、Curtis J. W. Walton、James L. Galman、Nicholas J. Turner、Roberto A. Chica

  DOI：10.1021/acscatal.9b00739

  日期：2019.4.5

  d-Tryptophan and its derivatives are important precursors of a wide range of indole-containing pharmaceuticals and natural products. Here, we developed a one-pot biocatalytic process enabling the synthesis of d-tryptophans from indoles in good yields and high enantiomeric excess (91% to >99%). Our method couples the synthesis of l-tryptophans catalyzed by Salmonella enterica tryptophan synthase with

  d-色氨酸及其衍生物是多种含吲哚的药物和天然产物的重要前体。在这里，我们开发了一种一锅式生物催化方法，能够从吲哚以高收率和高对映体过量（91％至> 99％）合成d-色氨酸。我们的方法联接的合成升-tryptophans通过催化肠道沙门氏菌色氨酸合酶与stereoinversion级联介导的变形杆菌myxofaciens升-氨基酸脱氨酶和转氨酶变体，我们工程改造，以显示天然样朝向活动d -色氨酸。我们的方法适用于各种d的制备级合成-在吲哚基团的所有苯环位置含有给电子或吸电子取代基的色氨酸衍生物。
• TRYPTOPHAN DERIVATIVES AS SWEETENERS
  申请人：Chromocell Corporation

  公开号：EP3720295A2

  公开（公告）日：2020-10-14
• COMPOSITIONS WITH SUGAR LIKE CHARACTERISTICS
  申请人：CORN Products Development Inc.

  公开号：EP3982756A1

  公开（公告）日：2022-04-20
• CYCLOHEXAPEPTIDES AS SELECTIVE SOMATOSTATIN SST5 RECEPTOR AGONISTS
  申请人：Heptares Therapeutics Limited

  公开号：US20210363188A1

  公开（公告）日：2021-11-25

  The disclosures herein relate to novel compounds of formula (1): (1) and salts thereof, wherein W, X, Y, Z, m, n, q, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are defined herein, and their use in treating, preventing, ameliorating, controlling or reducing the risk of disorders associated with somatostatin receptors.
• [EN] TRYPTOPHAN DERIVATIVES AS SWEETENERS<br/>[FR] DÉRIVÉS DE TRYPTOPHANE UTILISÉS COMME ÉDULCORANTS
  申请人：CHROMOCELL CORP

  公开号：WO2019113443A2

  公开（公告）日：2019-06-13

  The present disclosure provides compounds of Formula (I) and edible compositions comprising compounds of Formula (I) which are suitable for use as sweeteners, for example, by incorporation into edible compositions. Also provided herein are methods of preparing comestible compositions comprising compounds of Formula (I).