4-amino-4-deoxy chorismate | 133442-18-9

• 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: 4-amino-4-deoxy chorismate
• 英文别名: 4-Amino-4-deoxychorismic acid；(3R,4R)-4-amino-3-(1-carboxyethenoxy)cyclohexa-1,5-diene-1-carboxylic acid
• CAS: 133442-18-9
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: OIUJHGOLFKDBSU-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  分支酸 在 Escherichia coli p-aminodeoxyisochorismate synthase 、 glutaminase PabA 作用下， 生成 4-amino-4-deoxy chorismate
  参考文献：
  名称：

  与其反应产物异分支酸结合的大肠杆菌肠杆菌素特异性异分支酸合酶 (EntC) 的晶体结构：对利用分支酸的酶的酶机制和差异活性的影响

  摘要：

  EntC 是大肠杆菌中两种异分支酸合酶之一，专用于铁载体肠杆菌素的生物合成。在这里，我们报告了与异分支酸和 Mg 2+复合的 EntC 的晶体结构在 2.3 Å 分辨率下，具有非芳香反应产物的分支酸利用酶的第一个结构。EntC 与其他利用分支酸的酶（例如水杨酸合酶和邻氨基苯甲酸合酶）一样表现出复杂的 α+β 折叠。活性位点结构的比较允许鉴定几个以前没有讨论过的残基，这些残基可能对 EntC 的异分支酸活性很重要。尽管 EntC、MenF 和 Irp9 都将分支酸转化为异分支酸，但只有 Irp9 随后表现出异分支酸丙酮酸裂解酶活性，导致形成水杨酸和丙酮酸作为反应产物。为了了解这些氨基酸残基在分支酸向异分支酸转化中的作用，并获得有关 Irp9 丙酮酸裂解酶活性的线索，产生了几种 EntC 突变体，其中 EntC 中选定的残基被 Irp9 的残基取代：这些包括 A303T、L304A、F327Y、I346L

  DOI：

  10.1016/j.jmb.2010.01.019

文献信息

• (R)- SELECTIVE AMINATION
  申请人：DPX HOLDINGS B.V.

  公开号：US20160032335A1

  公开（公告）日：2016-02-04

  The present invention relates to a method for the enzymatic synthesis of enantiomerically enriched (R)-amines of general formula [1][c] from the corresponding ketones of the general formula [1][a] by using novel transaminases. These novel transaminases are selected from two different groups: either from a group of some 20 proteins with sequences as specified herein, or from a group of proteins having transaminase activity and isolated from a microorganism selected from the group of organisms consisting of Rahnella aquatilis, Ochrobactrum anthropi, Ochrobactrum tritici, Sinorhizobium morelense, Curtobacterium pusiffium, Paecilomyces lilacinus, Microbacterium ginsengisoli, Microbacterium trichothecenolyticum, Pseudomonas citronellolis, Yersinia kristensenii, Achromobacter spanius, Achromobacter insolitus, Mycobacterium fortuitum, Mycobacterium frederiksbergense, Mycobacterium sacrum, Mycobacterium fluoranthenivorans, Burkhoideria sp., Burkhoideria tropica, Cosmospora episphaeria , and Fusarium oxysporum.

  本发明涉及一种利用新型转氨酶从通式[1][a]的相应酮合成对映富集的(R)-胺的方法。这些新型转氨酶从两个不同的组中选择：一组具有如本文所述序列的约20种蛋白质，或者从具有转氨酶活性并从以下由Rahnella aquatilis、Ochrobactrum anthropi、Ochrobactrum tritici、Sinorhizobium morelense、Curtobacterium pusiffium、Paecilomyces lilacinus、Microbacterium ginsengisoli、Microbacterium trichothecenolyticum、Pseudomonas citronellolis、Yersinia kristensenii、Achromobacter spanius、Achromobacter insolitus、Mycobacterium fortuitum、Mycobacterium frederiksbergense、Mycobacterium sacrum、Mycobacterium fluoranthenivorans、Burkhoideriasp.、Burkhoideria tropica、Cosmospora episphaeria和Fusarium oxysporum组成的微生物中分离出的蛋白质组中选择。
• 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。
• MICROORGANISMS FOR THE PRODUCTION OF ANILINE
  申请人：Pharkya Priti

  公开号：US20110097767A1

  公开（公告）日：2011-04-28

  A non-naturally occurring microbial organism having an aniline pathway includes at least one exogenous nucleic acid encoding an aniline pathway enzyme expressed in a sufficient amount to produce aniline. The aniline pathway includes (1) an aminodeoxychorismate synthase, an aminodeoxychorismate lyase, and a 4-aminobenzoate carboxylyase or (2) an anthranilate synthase and an anthranilate decarboxylase. A method for producing aniline, includes culturing these non-naturally occurring microbial organisms under conditions and for a sufficient period of time to produce aniline.

  一种非自然生成的微生物有苯胺途径，包括至少一个外源核酸编码的苯胺途径酶，表达足够的量以产生苯胺。苯胺途径包括（1）一种氨基脱氧胆酸合成酶，一种氨基脱氧胆酸裂解酶和一种4-氨基苯甲酸羧化酶或（2）一种蒽醌合成酶和一种蒽醌脱羧酶。一种生产苯胺的方法，包括在适当的条件下培养这些非自然生成的微生物，并在足够的时间内产生苯胺。
• Sequence-determined DNA fragments and corresponding polypeptides encoded thereby
  申请人：Ceres Incorporated

  公开号：EP1033405A2

  公开（公告）日：2000-09-06

  The present invention provides DNA molecules that constitute fragments of the genome of a plant, and polypeptides encoded thereby. The DNA molecules are useful for specifying a gene product in cells, either as a promoter or as a protein coding sequence or as an UTR or as a 3' termination sequence, and are also useful in controlling the behavior of a gene in the chromosome, in controlling the expression of a gene or as tools for genetic mapping, recognizing or isolating identical or related DNA fragments, or identification of a particular individual organism, or for clustering of a group of organisms with a common trait. 0Arabidopsis DNA is used in the present experiment, but the procedure is a general one.

  本发明提供了构成植物基因组片段的 DNA 分子及其编码的多肽。这些 DNA 分子可作为启动子或蛋白质编码序列或 UTR 或 3'终止序列，用于指定细胞中的基因产物，也可用于控制染色体中基因的行为，控制基因的表达，或作为基因绘图、识别或分离相同或相关 DNA 片段、或识别特定生物个体、或对具有共同性状的生物群体进行聚类的工具。 本实验中使用的是拟南芥 DNA，但这是一个通用程序。
• 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。