(2R)-2-amino-6-hydroxy-4-hexynoic acid | 66183-64-0

• 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: (2R)-2-amino-6-hydroxy-4-hexynoic acid
• 英文别名: (2R)-2-amino-6-hydroxyhex-4-ynoic acid
• CAS: 66183-64-0
• 化学式: C₆H₉NO₃
• 分子量: 143.142
• InChiKey: HAPOKOYCNZZHNP-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (2RS)-2-amino-6-hydroxy-4-hexynoic acid 在 renal acylase sodium hydroxide 、 cobalt(II) acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 27.0h， 生成 (2R)-2-amino-6-hydroxy-4-hexynoic acid
  参考文献：
  名称：

  (2R)-2-AMINO-6-HYDROXY-4-HEXYNOIC acid, and related amino acids in the fruiting bodies of amanita MICULIFERA fn1 fn1Dedicated to Prof. G. H. N. Towers on the occasion of his 75th birthday. Part 25 in the series ‘‘Biochemical studies on nitrogen compounds of fungi’’. For Part 24, see ref. [5]. in honour of professor G.H. Neil Towers 75th birthday

  摘要：

  从Amanita miculifera的子实体中分离并鉴定了(2R)-2-氨基-6-羟基-4-己炔酸、(2RS)-2-氨基-4,5-己二烯酸、(2S)-2-氨基-4-己炔酸和2-氨基-5-氯-5-己烯酸,其中前两种和最后一种均为新发现的天然产物。其结构通过分析元素分析、KMnO4氧化、光旋转测定、氢-1核磁共振光谱和Adams或Lindlar催化剂的加氢反应结果确定。通过肾酰酶将(2RS)-2-氨基-6-羟基-4-己炔酸进行光学分解,证实了其天然的(2R)构型。2-氨基-4,5-己二烯酸在C-2的位置的构型也根据其ORD光谱推测得出,同时其加氢产物的光谱也支持了这一结论。由于2-氨基-5-氯-5-己烯酸的光旋转未测定(因其分离量极微),且其由2-氨基-5-己炔酸制备而成(但产率极低),因此未确定其详细结构。本文还提出了一种可能的生物合成途径,以说明该真菌中非蛋白质氨基酸的形成机制。 (C) 1998 Elsevier Science Ltd. 版权所有。

  DOI：

  10.1016/s0031-9422(98)00177-0

文献信息

• (2R)-2-AMINO-6-HYDROXY-4-HEXYNOIC acid, and related amino acids in the fruiting bodies of amanita MICULIFERA fn1 fn1Dedicated to Prof. G. H. N. Towers on the occasion of his 75th birthday. Part 25 in the series ‘‘Biochemical studies on nitrogen compounds of fungi’’. For Part 24, see ref. [5]. in honour of professor G.H. Neil Towers 75th birthday
  作者：Shin-Ichi Hatanaka、Yukio Niimura、Kunio Takishima、Junta Sugiyama

  DOI：10.1016/s0031-9422(98)00177-0

  日期：1998.9

  (2R)-2-amino-6-hydroxy-4-hexynoic acid, (2RS)-2-amino-4, 5-hexadienoic acid, (2S)-2-amino-4-hexynoic acid, and 2-amino-5-chloro-5-hexenoic acid were isolated and characterised from the fruit bodies of Amanita miculifera, with the first and the last mentioned amino acids being new natural products. Their structures were based on analysis of the results from elementary analysis, oxidation with KMnO4, determination of optical rotations, H-1 NMR-spectra, and hydrogenation over Adams or Lindlar catalysts. (2RS)-2-Amino-6-hydroxy-4-hexynoic acid was synthesized and optically resolved by renal acylase to confirm its natural (2R)configuration. The configuration at C-2 of 2-amino-4,5-hexadienoic acid was also assumed from its ORD spectrum, as well as that of its hydrogenation product. The optical rotation (2-amino-5-chloro-5-hexenoic acid) was not determined because it was isolated in trace amounts; it was also prepared from 2-amino-5-hexynoic acid, although in very low yield. A possible biosynthetic route leading to the non-protein amino acids in this fungus is presented. (C) 1998 Elsevier Science Ltd. All rights reserved.

  从Amanita miculifera的子实体中分离并鉴定了(2R)-2-氨基-6-羟基-4-己炔酸、(2RS)-2-氨基-4,5-己二烯酸、(2S)-2-氨基-4-己炔酸和2-氨基-5-氯-5-己烯酸,其中前两种和最后一种均为新发现的天然产物。其结构通过分析元素分析、KMnO4氧化、光旋转测定、氢-1核磁共振光谱和Adams或Lindlar催化剂的加氢反应结果确定。通过肾酰酶将(2RS)-2-氨基-6-羟基-4-己炔酸进行光学分解,证实了其天然的(2R)构型。2-氨基-4,5-己二烯酸在C-2的位置的构型也根据其ORD光谱推测得出,同时其加氢产物的光谱也支持了这一结论。由于2-氨基-5-氯-5-己烯酸的光旋转未测定(因其分离量极微),且其由2-氨基-5-己炔酸制备而成(但产率极低),因此未确定其详细结构。本文还提出了一种可能的生物合成途径,以说明该真菌中非蛋白质氨基酸的形成机制。 (C) 1998 Elsevier Science Ltd. 版权所有。