avenic acid A | 76224-57-2

• 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: avenic acid A
• 英文别名: (S,S,S)-avenic acid A；(2S)-4-[[(1S)-1-carboxy-3-hydroxypropyl]amino]-2-[[(3S)-3-carboxy-3-hydroxypropyl]amino]butanoic acid
• CAS: 76224-57-2
• 化学式: C₁₂H₂₂N₂O₈
• 分子量: 322.315
• InChiKey: QUKMQOBHQMWLLR-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.6
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  176
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (S)-2-((S)-3-Carboxy-3-hydroxy-propylamino)-4-((S)-2-oxo-tetrahydro-furan-3-ylamino)-butyric acid; compound with trifluoro-acetic acid 在 氢氧化钾 、 Dowex 50Wx₄ resin (H(+) form) 作用下， 生成 avenic acid A
  参考文献：
  名称：

  (+)-AVENIC ACID A的合成

  摘要：

  燕麦酸A(2)是燕麦根分泌的金属螯合剂，被认为是直接参与铁等元素吸收和转运的因子，由LN[3-羟基-3-羧丙基]高效合成高丝氨酸醛，它可能是一种生物合成前体。

  DOI：

  10.1246/cl.1981.827

文献信息

• A Unified Approach to Phytosiderophore Natural Products
  作者：Nicolas Kratena、Tobias Gökler、Lara Maltrovsky、Eva Oburger、Christian Stanetty

  DOI：10.1002/chem.202004004

  日期：2021.1.7

  the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative „east‐to‐west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l‐malic acid, threonines) were

  这项工作报告了 mugineic 酸和 avenic 酸家族（植物铁载体）的八种天然产物的简明全合成。三聚体产品的创新“从东到西”组装产生了高度的差异，使得最终产品的形成只需 10 或 11 个步骤，每个步骤所需的整体合成工作量最少。手性池起始材料（l-苹果酸、苏氨酸）用于外部构建单元，而中间构建单元通过非对映和对映选择性方法获得。这项工作的一个亮点在于直接制备差向异构羟基氮杂环丁烷氨基酸，它们本身就是有用的组成部分，从而能够首次合成 3''-羟基麦根酸和 3''-羟基-2'-脱氧麦根酸。
• SYNTHESIS OF AVENIC ACID A AND 2′-DEOXYMUGINEIC ACID, AMINO ACIDS POSSESSING AN IRON CHELATING ACTIVITY
  作者：Shinji Fushiya、Yoshikazu Sato、Shuichi Nakatsuyama、Norio Kanuma、Shigeo Nozoe

  DOI：10.1246/cl.1981.909

  日期：1981.7.5

  Avenic acid A (1), an amino acid derivative possessing an iron chelating activity and excreted from the root of Avena sativa L. was synthesized in optically active form by successive reductive coupling of protected L-aspartic β-semialdehyde and L-malic semialdehyde with L-homoserine lactone. 2′-Deoxymugineic acid (2), a related substance was also synthesized by the same method by which the stereostructure

  Avenic acid A (1) 是一种氨基酸衍生物，具有铁螯合活性，从 Avena sativa L. 的根中分泌出来，通过受保护的 L-天冬氨酸 β-半醛和 L-苹果酸半醛与 L-天冬氨酸 β-半醛和 L-苹果半醛的连续还原偶联，以旋光形式合成。 L-高丝氨酸内酯。2'-脱氧麦根酸(2)，也用同样的方法合成了相关物质，证明该氨基酸衍生物的立体结构为2(S),3'(S),3"(S)-N -[3-(3-羟基-3-羧丙基氨基)-3-羧丙基]-氮杂环丁烷-2-羧酸。
• COMPOSITIONS AND METHODS OF DELIVERING MOLECULES TO PLANTS
  申请人：Bloomsburg University of Pennsylvania

  公开号：US20170298374A1

  公开（公告）日：2017-10-19

  Compositions and method of delivering a molecule to a plant are provided. In an embodiment, an avenic acid transporter is introduced into a plant. The plant may be a non-graminacious or dicotyledonous plant which does not comprise the transporter in the wild type form. The transporter may be modified to increase uptake of avenic acid along with iron chelated by the avenic acid and/or a molecule conjugated with the avenic acid. Further embodiments provide for conjugating the avenic acid with a molecule for uptake and delivery to the plant. In this manner plant health may be improved by uptake of iron where it would otherwise not occur and/or uptake of the conjugated molecule. The molecule may be a molecule that improves health of the plant. Still further embodiments provide for analogs of avenic acid. Embodiments provide for interplanting Avena sativa which natively produces avenic acid with another plant. Additional embodiments provide for time release of avenic acid provided to a plant.

  本发明提供了向植物传递分子的组合物和方法。在一种实施例中，将avenic酸转运蛋白引入植物中。该植物可以是非禾本科或双子叶植物，其野生型不包括该转运蛋白。可以修改转运蛋白以增加avenic酸及其螯合的铁和/或与avenic酸结合的分子的摄取。进一步实施例提供了将avenic酸与分子结合以摄取和传递到植物中的方法。通过这种方式，可以通过摄取铁，否则不会发生，并/或摄取结合的分子来改善植物的健康状况。该分子可以是改善植物健康的分子。还有进一步的实施例提供avenic酸的类似物。实施例提供了将天然产生avenic酸的燕麦（Avena sativa）与其他植物相互种植的方法。另外的实施例提供了向植物提供avenic酸的时间释放。
• COMPOSITIONS AND METHODS FOR DELIVERY OF MOLECULES TO PLANTS
  申请人：BLOOMSBURG UNIVERSITY OF PENNSYLVANIA

  公开号：US20190323025A1

  公开（公告）日：2019-10-24

  Compositions and methods are provided where a plant comprising an avenic acid transporter is planted in a field with a target plant in need of increased iron uptake. The plant comprising the avenic acid transporter in an embodiment further comprises one or more constructs comprising nucleic acid molecules expressing heavy and light chains forming an antibody specific to the avenic acid transporter or functional small peptide and may also include a sequence targeting the apoplast. The antibody or functional small peptide is operably linked to a floral promoter or inducible natural or synthetic promoter. Upon expression regulated by the floral promoter or exposure to the inducing conditions, or both, the plant increases its production of avenic acid transporter antibodies, enters senescence and eventually dies. As a result, the plant is not harvested with the target plant, provides a cover crop, and does not continue to use nutrients, and other resources that benefit the targeted plant. Increased avenic acid is produced by the plant prior to dying in response to Fe 3+ starvation induced by inactivation of the Fe +3 /phytosiderophore transporter.

  本发明提供了一种组合物和方法，其中在需要增加铁吸收的目标植物的田地中种植了一种含有avenic酸转运蛋白的植物。在一种实施例中，含有avenic酸转运蛋白的植物进一步包括一个或多个构建，包括表达重链和轻链形成特异性抗avenic酸转运蛋白或功能小肽的核酸分子，并且还可以包括一个靶向细胞外质的序列。抗体或功能小肽与花促进子或诱导天然或合成促进子可操作地链接。在通过花促进子调节表达或暴露于诱导条件下，或两者兼有的情况下，植物增加了其avenic酸转运蛋白抗体的产量，进入衰老并最终死亡。因此，该植物不会与目标植物一起收获，提供了一种覆盖作物，并且不会继续使用有益于目标植物的营养和其他资源。在由于Fe3+饥饿诱导Fe+3/植酸类物质转运蛋白失活而死亡之前，植物会产生增加的avenic酸。
• Compositions and methods of delivering molecules to plants
  申请人：Bloomsburg University of Pennsylvania

  公开号：US10563216B2

  公开（公告）日：2020-02-18

  Compositions and method of delivering a molecule to a plant are provided. In an embodiment, an avenic acid transporter is introduced into a plant. The plant may be a non-graminacious or dicotyledonous plant which does not comprise the transporter in the wild type form. The transporter may be modified to increase uptake of avenic acid along with iron chelated by the avenic acid and/or a molecule conjugated with the avenic acid. Further embodiments provide for conjugating the avenic acid with a molecule for uptake and delivery to the plant. In this manner plant health may be improved by uptake of iron where it would otherwise not occur and/or uptake of the conjugated molecule. The molecule may be a molecule that improves health of the plant. Still further embodiments provide for analogs of avenic acid. Embodiments provide for interplanting Avena sativa which natively produces avenic acid with another plant. Additional embodiments provide for time release of avenic acid provided to a plant.

  提供了向植物输送分子的组合物和方法。在一个实施方案中，将枳实酸转运体引入植物。该植物可以是不含野生型转运体的非禾本科或双子叶植物。可以对转运体进行修饰，以增加对枳实酸以及被枳实酸螯合的铁和/或与枳实酸共轭的分子的吸收。更进一步的实施方案提供了将枳实酸与一种分子共轭以便植物吸收和输送的方法。通过这种方式，植物的健康可通过吸收本来不会吸收的铁和/或吸收共轭分子而得到改善。该分子可以是改善植物健康的分子。更进一步的实施方案提供了枳实酸的类似物。本发明的实施例提供了将原生可产生枳椇酸的枳椇草与另一种植物间种的方法。另外的实施方案提供了向植物提供的枳椇酸的时间释放。