5-deoxy-5-amino-shikimic acid | 178948-66-8

• 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: 5-deoxy-5-amino-shikimic acid
• 英文别名: 5-Aminoshikimate；(3R,4S,5R)-5-azaniumyl-3,4-dihydroxycyclohexene-1-carboxylate
• CAS: 178948-66-8
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: GSAKPGCLECHWSP-PBXRRBTRSA-N

物化性质

• 沸点：
  403.0±45.0 °C(Predicted)
• 密度：
  1.552±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-deoxy-5-amino-shikimic acid 在 sodium hydroxide 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以60%的产率得到5-脱氧-5-氨基-3-脱氢莽草酸
  参考文献：
  名称：

  安沙霉素抗生素中 mC7N 单位的前体 3-氨基-5-羟基苯甲酸的生物合成†

  摘要：

  使用利福霉素 B 生产者 Amycolatopsis mediterranei S699 和 Ansatrienin A 生产者 Streptomyces collinus Tu1892 的无细胞提取物研究了 3-氨基-5-羟基苯甲酸 (AHBA) 形成的生物合成途径。磷酸烯醇式丙酮酸 (PEP) 加赤藓糖 4-磷酸 (E4P) 以低但仍然显着 (6%) 的产率得到 AHBA。3,4-Dideoxy-4-amino-d-arabino-heptulosonic acid 7-phosphate (aminoDAHP) 被有效地转化为 AHBA (45%)，5-deoxy-5-amino-3-dehydroquinic acid (aminoDHQ, 41 %) 和 5-deoxy-5-amino-3-dehydroshikimic 酸 (aminoDHS, 95%)。另一方面，正常莽草酸途径中间体

  DOI：

  10.1021/ja9601292
• 作为产物：
  描述：

  methyl shikimate 在 氢氧化钾 、 sodium azide 、 水 、 氢气 、 氯化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 生成 5-deoxy-5-amino-shikimic acid
  参考文献：
  名称：

  两种新型EPSP合酶抑制剂的合成与评价

  摘要：

  EPSP合酶EPSPS（EC 2.5.1.19）催化烯醇丙酮酸部分从磷酸烯醇丙酮酸（，PEP）区域特异性地转移到sh草酸酯3-磷酸​​酯（，S3P）的5-OH形成5-烯醇-磷酸丙酮酰草酸酯3-磷酸酯（，EPSP）。制备了两种新的抑制剂（和）来探测S3P结合位点。

  DOI：

  10.1016/s0040-4039(00)78792-2

文献信息

• Process for the preparation of 4,5-diamino shikimic acid derivatives
  申请人：Karpf Martin

  公开号：US20060047002A1

  公开（公告）日：2006-03-02

  The present invention relates to a process for the preparation of a 4,5-diamino shikimic acid derivative of formula and pharmaceutically acceptable addition salts thereof wherein R 1 , R 1′ are independent of each other H or alkyl, R 2 is an alkyl and R 3 , R 4 are independent of each other H or an alkanoyl, with the proviso that not both R 3 and R 4 are H. 4,5-diamino shikimic acid derivatives of formula I, especially the (3R,4R,5S)-5-amino-4-acetylamino-3-(1-ethyl-propoxy)-cyclohex-1-ene-carboxylic acid ethyl ester and its pharmaceutically acceptable additional salts are potent inhibitors of viral neuraminidase.

  本发明涉及一种制备4,5-二氨基香草酸衍生物的方法，其化学式为及其药学上可接受的加成盐，其中R1，R1'独立地为H或烷基，R2为烷基，R3，R4独立地为H或脂肪酰基，但R3和R4不同时为H。化合物I的4,5-二氨基香草酸衍生物，特别是(3R，4R，5S)-5-氨基-4-乙酰氨基-3-(1-乙基-丙氧基)-环己-1-烯-羧酸乙酯及其药学上可接受的加成盐是病毒神经氨酸酶的有效抑制剂。
• Polynucleotides for production of farnesyl dibenzodiazepinones
  申请人：Farnet M. Chris

  公开号：US20060172395A1

  公开（公告）日：2006-08-03

  This invention provides genes and their encoded proteins, involved in the biosynthesis of farnesyl dibenzodiazepinones, including ECO-04601. The invention relates to expression vectors comprising the genes and to host cell transformed with these vectors. The invention further relates to methods of producing farnesyl dibenzodiazepinone compounds using the genes and proteins of the invention, for example, involving expression of biosynthetic pathway genes in transformed host cells.

  该发明提供了参与法尼酰二苯并二氮环酮（包括ECO-04601）生物合成的基因及其编码的蛋白质。该发明涉及包含这些基因的表达载体以及转化为这些载体的宿主细胞。该发明进一步涉及使用该发明中的基因和蛋白质生产法尼酰二苯并二氮环酮化合物的方法，例如在转化的宿主细胞中表达生物合成途径基因。
• Farnesyl dibenzodiazepinone, processes for its production and its use as a pharmaceutical
  申请人：Bachmann O. Brian

  公开号：US20050043297A1

  公开（公告）日：2005-02-24

  This invention relates to a novel farnesylated dibenzodiazepinone, named ECO-04601, its pharmaceutically acceptable salts and derivatives, and to methods for obtaining such compounds. One method of obtaining the ECO-04601 compound is by cultivation of a novel strain of Micromonospora sp., 046-ECO11; another method involves expression of biosynthetic pathway genes in transformed host cells. The present invention further relates to Micromonospora sp. strain 046-ECO11, to the use of ECO-04601 and its pharmaceutically acceptable salts and derivatives as pharmaceuticals, in particular to their use as inhibitors of cancer cell growth, bacterial cell growth, mammalian lipoxygenase, and to pharmaceutical compositions comprising ECO-04601 or a pharmaceutically acceptable salt or derivative thereof. Finally, the invention relates to novel polynucleotide sequences and their encoded proteins, which are involved in the biosynthesis of ECO-04601.

  本发明涉及一种新型的法尼酰化二苯并二氮杂环酮，命名为ECO-04601，其药学上可接受的盐和衍生物，以及获得这种化合物的方法。获得ECO-04601化合物的一种方法是通过培养一种新的微单孢菌株，046-ECO11；另一种方法涉及在转化的宿主细胞中表达生物合成途径基因。本发明还涉及微单孢菌株046-ECO11的使用，以及ECO-04601及其药学上可接受的盐和衍生物作为药物的使用，特别是作为癌细胞生长抑制剂、细菌细胞生长抑制剂、哺乳动物脂肪氧合酶抑制剂，以及包含ECO-04601或其药学上可接受的盐或衍生物的药物组合物。最后，本发明涉及新的多核苷酸序列及其编码的蛋白质，这些蛋白质参与ECO-04601的生物合成。
• Farnesyl dibenzodiazepinone and processes for its production
  申请人：McAlpine James B.

  公开号：US20080199940A1

  公开（公告）日：2008-08-21

  This invention relates to a novel farnesylated dibenzodiazepinone, named ECO-04601, its pharmaceutically acceptable salts and derivatives, and to methods for obtaining such compounds. One method of obtaining the ECO-04601 compound is by cultivation of a novel strain of Micromonospora sp., 046-ECO11; another method involves expression of biosynthetic pathway genes in transformed host cells. The present invention further relates to Micromonospora sp. strain 046-ECO11, to the use of ECO-04601 and its pharmaceutically acceptable salts and derivatives as pharmaceuticals, in particular to their use as inhibitors of cancer cell growth, bacterial cell growth, mammalian lipoxygenase, and to pharmaceutical compositions comprising ECO-04601 or a pharmaceutically acceptable salt or derivative thereof. Finally, the invention relates to novel polynucleotide sequences and their encoded proteins, which are involved in the biosynthesis of ECO-04601.

  本发明涉及一种新型的法尼醇基二苯并二氮杂环酮，命名为ECO-04601，其药物可接受的盐和衍生物，以及获得这种化合物的方法。获得ECO-04601化合物的一种方法是通过培养一种新的微单孢菌株Micromonosporasp. 046-ECO11; 另一种方法涉及在转化的宿主细胞中表达生物合成途径基因。本发明还涉及Micromonosporasp.株046-ECO11的使用，以及ECO-04601及其药物可接受的盐和衍生物作为药物的使用，特别是作为癌细胞生长抑制剂，细菌细胞生长抑制剂，哺乳动物脂氧合酶以及包含ECO-04601或其药物可接受的盐或衍生物的药物组合物。最后，本发明涉及新的多核苷酸序列及其编码的蛋白质，这些蛋白质参与ECO-04601的生物合成。
• FARNESYL DIBENZODIAZEPINONE AND PROCESSES FOR ITS PRODUCTION
  申请人：ZAZOPOULOS Emmanuel

  公开号：US20090263886A1

  公开（公告）日：2009-10-22

  This invention relates to a novel farnesylated dibenzodiazepinone, named ECO-04601, its pharmaceutically acceptable salts and derivatives, and to methods for obtaining such compounds. One method of obtaining the ECO-04601 compound is by cultivation of a novel strain of Micromonospora sp., 046-ECO11; another method involves expression of biosynthetic pathway genes in transformed host cells. The present invention further relates to Micromonospora sp. strain 046-ECO11, to the use of and its pharmaceutically acceptable salts and derivatives as pharmaceuticals, in particular to their use as inhibitors of cancer cell growth, bacterial cell growth, mammalian lipoxygenase, and to pharmaceutical compositions comprising ECO-04601 or a pharmaceutically acceptable salt or derivative thereof. Finally, the invention relates to novel polynucleotide sequences and their encoded proteins, which are involved in the biosynthesis of ECO-04601.

  本发明涉及一种新型的法尼酰化二苯并二氮平酮，名为ECO-04601，其药学上可接受的盐和衍生物，以及获得这种化合物的方法。获得ECO-04601化合物的一种方法是通过培养一种新的微单孢菌株Micromonosporasp.，046-ECO11；另一种方法涉及在转化的宿主细胞中表达生物合成途径基因。本发明还涉及Micromonosporasp.株系046-ECO11的使用及其药学上可接受的盐和衍生物作为药物，特别是它们作为抑制癌细胞生长、细菌细胞生长、哺乳动物脂氧合酶的药物的使用，以及包含ECO-04601或其药学上可接受的盐或衍生物的药物组合物。最后，本发明涉及新的多核苷酸序列及其编码的蛋白质，这些蛋白质参与ECO-04601的生物合成。