(3R,4R)-4-amino-3-hydroxy-cyclohexa-1,5-diene carboxylic acid | 870246-44-9

• 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: (3R,4R)-4-amino-3-hydroxy-cyclohexa-1,5-diene carboxylic acid
• 英文别名: (3R,4R)-4-amino-3-hydroxycyclohexa-1,5-dienecarboxylic acid；(3R,4R)-4-amino-3-hydroxycyclohexa-1,5-diene-1-carboxylic acid
• CAS: 870246-44-9
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: XNJQUGOZDRJYQG-PHDIDXHHSA-N

物化性质

• 沸点：
  389.1±42.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-amino-3-hydroxy-cyclohexa-1,5-diene carboxylic acid 在 盐酸 、 碳酸氢钠 、 氯甲酸异丙酯 、 三乙胺 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 叔丁醇 为溶剂， 生成
  参考文献：
  名称：

  分支酸酯衍生的多样性产物的生产及其在有机合成中的应用

  摘要：

  以生物合成为模型：基于生物合成途径（例如the草酸途径）的分支结构，通过代谢工程（参见方案）已经实现了多种多样代谢产物的选择性生物生产。进行了用于制备目的的放大生产，从而导致较高的产品效价和可再生资源的产量。

  DOI：

  10.1002/anie.201103261

文献信息

• β- and σ-Amino acids (2,3- and 3,4-trans-CHA) as catalysts in Knoevenagel condensation and asymmetric aldol reactions
  作者：Lo’ay Ahmed Al-Momani、Volker Lorbach、Jean Detry、Petra Geilenkirchen、Michael Müller

  DOI：10.24820/ark.5550190.p009.854

  日期：——

  as catalysts in Knoevenagel condensation and aldol addition reactions is studied. Synthesis of the zinc(II) complexes of 2,3and 3,4-trans-CHA provided precipitated material of sufficient purity for use. The catalytic Knoevenagel reactions were carried out with the β-amino acid 2,3-trans-CHA and the δ-amino acid 3,4-trans-CHA, resulting in a product yield of up to 61%. The asymmetric aldol addition reactions

  β和δ-氨基酸（5S，6S）-6-氨基-5-羟基环六-1,3-二烯羧酸（2,3-反式-CHA）和（3R,4R）-4-氨基-3的功效-羟基环己-1,5-二烯羧酸（3,4-反式-CHA）作为Knoevenagel缩合和羟醛加成反应的催化剂进行了研究。2,3-和3,4-反式-CHA的锌(II)配合物的合成提供了足够纯度的沉淀物质供使用。用β-氨基酸2,3-反式-CHA和δ-氨基酸3,4-反-CHA进行催化Knoevenagel反应，产物收率高达61%。不对称醛醇加成反应是用催化量的 2,3-和 3,4-反式-CHA 的锌 (II) 配合物进行的。在这种情况下，观察到产物的 ee（高达 90%）取决于转化率和/或反应时间。
• Biosynthetic Production of 4-Amino 4-Deoxychorismate (Adc) and [3R,4R]-4-Amino-3-Hydroxycyclohexa-1,5-Diene-1-Carboxylic Acid (3,4-Cha)
  申请人：Wubbolts Marcel Gerhardus

  公开号：US20080311631A1

  公开（公告）日：2008-12-18

  The invention relates to a process for the biosynthetic production of 4-amino-4-deoxychorismate (ADC) performed fermentatively in vivo with a 4-amino-4-deoxychorismate synthase, preferably a PabAB bipartite protein (which may be a fusion protein), at an increased level of activity, thereby obtaining a broth comprising ADC and 4-amino-4-deoxyprephenate (ADP), that are recovered. The invention also relates to a further process of converting the ADP into p-aminophenylalanine. The invention, moreover relates to biosynthetic production of [3R,4R]-4-amino-3-hydroxycyclohexa-1,5-diene-1-carboxylic acid (3,4-CHA), by concerted action of such 4-amino-4-deoxychorismate synthase and of an enzyme capable of converting isochorismate into [5S,6S]-5,6 dihydroxycyclohexa-1,3-diene-1-carboxylic acid (2,3-CHD), preferably a phenazine biosynthesis protein PhzD, including recovery of 3,4-CHA. The invention also relates to expression vectors and host cells for use in any of such processes. The invention further relates to the use of 3,4-CHA as a catalytically active product, in particular as a chiral catalyst. And the invention finally relates to synthesis of oseltamivir phosphate from 3,4-CHA.

  该发明涉及一种生物合成4-氨基-4-脱氧黄嘌呤酸（ADC）的过程，通过在体内发酵使用4-氨基-4-脱氧黄嘌呤酸合成酶，优选为PabAB二分体蛋白（可为融合蛋白）在增加的活性水平下进行，从而获得包含ADC和4-氨基-4-脱氧前苯酸（ADP）的菌液，然后进行回收。该发明还涉及将ADP转化为对氨基苯丙氨酸的进一步过程。此外，该发明还涉及通过这种4-氨基-4-脱氧黄嘌呤酸合成酶和能够将异黄嘌呤酸转化为[5S，6S]-5,6-二羟基环己基-1,3-二烯-1-羧酸（2,3-CHD）的酶的协同作用，优选为苯肼生物合成蛋白PhzD，生物合成[3R,4R]-4-氨基-3-羟基环己-1,5-二烯-1-羧酸（3,4-CHA），并回收3,4-CHA。该发明还涉及用于任何这种过程的表达载体和宿主细胞。此外，该发明还涉及将3,4-CHA用作具有催化活性的产品，特别是作为手性催化剂。最后，该发明还涉及从3,4-CHA合成奥司他韦磷酸盐的方法。
• Biosynthetic production of 4-amino-4-deoxychorismate (ADC) and [3R,4R]-4-amino-3-hydroxycyclohexa-1,5-diene-1-carboxylic acid (3,4-CHA)
  申请人：DSM IP Assets B.V.

  公开号：EP1602730A2

  公开（公告）日：2005-12-07

  The invention relates to a process for the biosynthetic production of 4-amino-4-deoxychorismate (ADC) performed fermentatively in vivo with a 4-amino-4-deoxychorismate synthase, preferably a PabAB bipartite protein (which may be a fusion protein), at an increased level of activity, thereby obtaining a broth comprising ADC and 4-amino-4-deoxyprephenate (ADP), that are recovered. The invention also relates to a further process of converting the ADP into p-aminophenylalanine. The invention, moreover relates to biosynthetic production of [3R,4R]-4-amino-3-hydroxycyclohexa-1,5-diene-1-carboxylic acid (3,4-CHA), by concerted action of such 4-amino-4-deoxychorismate synthase and of an enzyme capable of converting isochorismate into [5S,6S]-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylic acid (2,3-CHD), preferably a phenazine biosynthesis protein PhzD, including recovery of 3,4-CHA. The invention also relates to expression vectors and host cells for use in any of such processes. And the invention finally relates to synthesis of oseltamivir phosphate from 3,4-CHA.

  本发明涉及一种生物合成生产4-氨基-4-脱氧胆甾酸盐（ADC）的工艺，该工艺在体内发酵，使用活性水平提高的4-氨基-4-脱氧胆甾酸盐合成酶，最好是PabAB双蛋白（可以是融合蛋白），从而获得由ADC和4-氨基-4-脱氧苯甲酸盐（ADP）组成的肉汤，并进行回收。本发明还涉及将 ADP 转化为对氨基苯丙氨酸的进一步工艺。此外，本发明还涉及通过这种 4-氨基-4-脱氧胆甾酸合成酶和一种能将异胆甾酸转化为 [5S.6S]-5,6- 二烯-1-羧酸的酶的协同作用，生物合成生产 [3R,4R]-4-氨基-3-羟基环己-1,5-二烯-1-羧酸（3,4-CHA）、6S]-5,6-二羟基环己-1,3-二烯-1-羧酸（2,3-CHD）的酶，最好是酚嗪生物合成蛋白 PhzD，包括回收 3,4-CHA。本发明还涉及用于上述任何过程的表达载体和宿主细胞。最后，本发明还涉及从 3,4-CHA合成磷酸奥司他韦。
• BIOSYNTHETIC PRODUCTION OF 4-AMINO-4-DEOXYCHORISMATE (ADC) AND [3,4R]-4-AMINO-3-HYDROXYCYCLOHEXA-1,5-DIENE-1-CARBOXYLIC ACID (3,4-CHA)
  申请人：DSM IP Assets B.V.

  公开号：EP1751297A2

  公开（公告）日：2007-02-14
• [EN] BIOSYNTHETIC PRODUCTION OF 4-AMINO-4-DEOXYCHORISMATE (ADC) AND [3R,4R]-4-AMINO-3-HYDROXYCYCLOHEXA-1,5-DIENE-1-CARBOXYLIC ACID (3,4-CHA)<br/>[FR] PRODUCTION BIOSYNTHETIQUE DE 4-AMINO-4-DESOXYCHORISMATE (ADC) ET D'ACIDE (3,4-CHA) [3R,4R]-4-AMINO-3-HYDROXYCYCLOHEXA-1,5-DIENE-1-CARBOXYLIQUE
  申请人：DSM IP ASSETS BV

  公开号：WO2005118829A2

  公开（公告）日：2005-12-15

  The invention relates to a process for the biosynthetic production of 4-amino-4-deoxychorismate (ADC) performed fermentatively in vivo with a 4-amino-4-deoxychorismate synthase, preferably a PabAB bipartite protein (which may be a fusion protein), at an increased level of activity, thereby obtaining a broth comprising ADC and 4-amino-4-deoxyprephenate (ADP), that are recovered. The invention also relates to a further process of converting the ADP into p-aminophenylalanine. The invention, moreover relates to biosynthetic production of [3R,4R]-4-amino-3-hydroxycyclohexa-1,5-diene-1-carboxylic acid (3,4-CHA), by concerted action of such 4-amino-4-deoxychorismate synthase and of an enzyme capable of converting isochorismate into [5S,6S]-5,6 dihydroxycyclohexa-1,3-diene-1­carboxylic acid (2,3-CHD), preferably a phenazine biosynthesis protein PhzD, including recovery of 3,4-CHA. The invention also relates to expression vectors and host cells for use in any of such processes. The invention further relates to the use of 3,4-CHA as a catalytically active product, in particular as a chiral catalyst. And the invention finally relates to synthesis of oseltamivir phosphate from 3,4-CHA.