2-amino-5-(1H-indol-3-yl)-4-oxopentanoic 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: 2-amino-5-(1H-indol-3-yl)-4-oxopentanoic acid
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: SMZRZJFMYRBKMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4R)-2-amino-4-carboxy-4hydroxy-5-(1H-indol-3-yl)pentanoic acid 反应 24.0h， 生成 3-吲哚甲醛 、 3-吲哚甲酸 、 2-(2-formamidophenyl)isonicotinic acid 、 2-amino-5-(1H-indol-3-yl)-4-oxopentanoic acid 、 monatin lactone 、 2-hydroxymonatin
  参考文献：
  名称：

  Photostability study of natural high-potency sweetener monatin in a model beverage system and characterisation of the degradation products

  摘要：

  Photodegradation of the naturally occurring high-potency sweetener monatin was studied in a lemon-lime beverage model system under simulated conditions. Most of the monatin disappeared after treatment with the equivalent of four days of ultraviolet light exposure and resulted in the formation of a number of degradation products. These degradation products have been isolated and characterised in the present study. On the basis of these identified structures, a photodegradation pathway has been proposed suggesting that monatin gets oxidised on the indole C-2 position to result in 2-hydroxymonatin. It also undergoes decarboxylation resulting in a 4-oxopentanoic acid analog and a major rearrangement resulting in an isonicotinic acid analog. Monatin also degrades into 3-formylindole and indole-3-carboxylic acid. Besides these, a partial monatin dimer and a monatin lactone were identified as additional degradation products. Details of the isolation and characterisation are given. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2011.08.073

文献信息

• モナティン類及びその製造中間体の製造方法並びに新規中間体
  申请人：味の素株式会社

  公开号：JP2003171365A

  公开（公告）日：2003-06-20

  (57)【要約】\n【課題】甘味剤や飲食品等の甘味成分として期待できるモナティン類を工業的に効率良く製造する方法を提供する。\n【解決手段】適切な保護基を持つインドール酢酸誘導体とアスパラギン酸の酸ハロゲン化物を、好ましくは塩基の存在下に、反応させて調製した縮合物を脱炭酸、脱保護することにより、立体選択的に合成した新規ケトン誘導体、例えば2-アミノ-5-（3-インドリル）-4-オキソペンタン酸に対し、好ましくは塩基性条件下で、シアノヒドリン化を行い、得られたシアノヒドリン誘導体を塩基性条件下に加水分解工程によりモナティン類を得る。得られたモナティン類に対し、保護基を導入する等の誘導体化を行い、得られる誘導体の形態で精製を行った後に、脱保護反応を行い保護基を除去して、目的とする高純度のモナティン類を製造することができる。このように、モナティン類（モナティン或いはその立体異性体）の優れた製造方法、そのための重要な製造中間体の効率的な製造方法、更にはこのようにして得られる重要な新規中間体を提供する。

  (57) [摘要] Јn[问题] 提供一种工业上高效的生产莫纳亭的方法，莫纳亭有望用作食品和饮料等的甜味剂和甜味成分。 \解决方法：通过将带有适当保护基的吲哚乙酸衍生物与天冬氨酸的酸卤化物反应制备的缩合物进行脱羧和脱保护，最好是在碱存在下，立体选择性地合成一种新的酮衍生物，如2-氨基-5-(3-吲哚基)-4-. 氧代戊酸最好在碱性条件下进行氰醇化反应，得到的氰醇衍生物在碱性条件下水解得到一元胺。 得到的一元胺可以通过引入保护基团等进行衍生化，在以得到的衍生物形式纯化后，可以进行脱保护反应以去除保护基团，从而生产出所需的高纯度一元胺。 因此，本发明提供了一种生产一元胺（一元胺或其立体异构体）的极佳方法、一种生产用于此目的的重要生产中间体的有效方法，以及通过这种方法获得的重要的新中间体。
• Methods and Formulations for Inhibiting Degradation of Photosensitive Sweeteners and Sweetener Enhancers
  申请人：Upreti Mani

  公开号：US20120282377A1

  公开（公告）日：2012-11-08

  Methods of inhibiting the degradation of a photosensitive sweetener or a sweetness enhancer in a food or beverage formulation, the method comprising adding a photodegradation-inhibiting amount of one or more antioxidants to the food or beverage formulation; and/or packaging the food or beverage formulation in a UV absorbing container are provided. Food or beverage formulations comprising an antioxidant and a photosensitive sweetener or sweetness enhancer, and/or that is packaged in a UV absorbing package or dark-colored package are also provided.
• [EN] METHODS AND FORMULATIONS FOR INHIBITING DEGRADATION OF PHOTOSENSITIVE SWEETENERS AND SWEETENER ENHANCERS<br/>[FR] PROCÉDÉS ET FORMULATIONS POUR INHIBER LA DÉGRADATION D'ÉDULCORANTS ET ACTIVATEURS D'ÉDULCORANTS PHOTOSENSIBLES
  申请人：COCA COLA CO

  公开号：WO2012151587A1

  公开（公告）日：2012-11-08

  Methods of inhibiting the degradation of a photosensitive sweetener or a sweetness enhancer in a food or beverage formulation, the method comprising adding a photodegradation-inhibiting amount of one or more antioxidants to the food or beverage formulation; and/or packaging the food or beverage formulation in a UV absorbing container are provided. Food or beverage formulations comprising an antioxidant and a photosensitive sweetener or sweetness enhancer, and/or that is packaged in a UV absorbing package or dark-colored package are also provided.
• Photostability study of natural high-potency sweetener monatin in a model beverage system and characterisation of the degradation products
  作者：Mani Upreti、Kasi V. Somayajula、Dennis J. Milanowski、Peter Kowalenko、Ulla Mocek、Rafael San Miguel、Indra Prakash

  DOI：10.1016/j.foodchem.2011.08.073

  日期：2012.3

  Photodegradation of the naturally occurring high-potency sweetener monatin was studied in a lemon-lime beverage model system under simulated conditions. Most of the monatin disappeared after treatment with the equivalent of four days of ultraviolet light exposure and resulted in the formation of a number of degradation products. These degradation products have been isolated and characterised in the present study. On the basis of these identified structures, a photodegradation pathway has been proposed suggesting that monatin gets oxidised on the indole C-2 position to result in 2-hydroxymonatin. It also undergoes decarboxylation resulting in a 4-oxopentanoic acid analog and a major rearrangement resulting in an isonicotinic acid analog. Monatin also degrades into 3-formylindole and indole-3-carboxylic acid. Besides these, a partial monatin dimer and a monatin lactone were identified as additional degradation products. Details of the isolation and characterisation are given. (C) 2011 Elsevier Ltd. All rights reserved.