N2-benzyloxycarbonyl-N5-benzylidene-L-ornithine | 250215-07-7

• 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: N2-benzyloxycarbonyl-N5-benzylidene-L-ornithine
• 英文别名: (2S)-5-(benzylideneamino)-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 250215-07-7
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: HPVBVKUBGUMWGF-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N2-benzyloxycarbonyl-N5-benzylidene-L-ornithine 在 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S,Z)-N-benzylidene-4-(benzyloxycarbonylamino)-4-carboxybutan-1-amine oxide
  参考文献：
  名称：

  Practical Synthesis of Hydroxamate-Derived Siderophore Components by an Indirect Oxidation Method and Syntheses of a DIG−Siderophore Conjugate and a Biotin−Siderophore Conjugate

  摘要：

  A practical large-scale synthesis of hydroxamate-derived siderophore components (30 and 40) that utilizes an efficient indirect oxidation method is described and applied to the syntheses of nonradioactive labeled siderophores. Oxidation of imines derived from L-ornithine (17) and its tripeptide (19) afforded oxaziridines that were isomerized to stable-nitrones (16 and 18). Acid-catalyzed hydrolysis of nitrones provided hydroxylamines that were converted to the desired hydroxamic acids (30 and 40) suitable for constructing siderophore-drug conjugates (2). The entire synthetic sequence required no chromatographic separation. DIG- and biotin-labeled ferrichrome analogues designed to detect and isolate ferrichrome receptors in various microbes were also synthesized.

  DOI：

  10.1021/jo990769y
• 作为产物：
  描述：

  Cbz-L-鸟氨酸 、 苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 N2-benzyloxycarbonyl-N5-benzylidene-L-ornithine
  参考文献：
  名称：

  A 4-tert-butylcalix[4]arene tetrahydroxamate podand based on the 1-oxypiperidine-2-one (1,2-PIPO⁻) chelate. Self-assembly into a supramolecular ionophore driven by coordination of tetravalent zirconium or hafnium(iv)

  摘要：

  K⁺被四环羟肟基固定单元的calix[4]芳香烃醚podand 1H₄与四价锆或铪的2:2络合物包裹。

  DOI：

  10.1039/c4ra00977k

文献信息

• [EN] BACTERIAL SIDEROPHORE GRAMIBACTIN<br/>[FR] GRAMIBACTINE SIDÉROPHORE BACTÉRIENNE
  申请人：LEIBNIZ INST FUER NATURSTOFF FORSCHUNG

  公开号：WO2019115765A1

  公开（公告）日：2019-06-20

  The invention relates to a peptide siderophore, comprising one or more N-nitroso-hydroxylamine ligands. In a preferred embodiment, the peptide siderophore comprises two side chains, each with a N-nitroso-hydroxylamine ligand, and a further side chain with one or more hydroxy carboxylic acid, hydroxamate, catecholate and/or salicylate ligands, wherein the siderophore is preferably cyclic. The invention further relates to a bacterial cell expressing a peptide siderophore of the invention and a composition comprising a peptide siderophore of the invention, for example in the form of its corresponding iron-complex, or bacteria of the invention. The invention further relates to a method for promoting plant growth, promoting root growth or development, improving stress tolerance in a plant and/or for increasing crop yields of a plant, and/or for delivering nitric oxide (NO) to a plant and/or for enhancing chlorophyll production in a plant by administering the peptide siderophore, bacteria expressing the peptide siderophore or a composition comprising the peptide siderophore to said plant.

  本发明涉及一种肽类铁载体，包括一个或多个N-亚硝基-羟胺配体。在一种优选实施例中，该肽类铁载体包括两个侧链，每个侧链都有一个N-亚硝基-羟胺配体，以及另一个侧链，该侧链具有一个或多个羟基羧酸、羟肟酸、邻二酚和/或水杨酸配体，其中该铁载体优选为环状。本发明还涉及一种表达该肽类铁载体的细菌细胞和一种包含该肽类铁载体的组合物，例如以其相应的铁络合物形式或本发明的细菌。本发明还涉及一种通过向植物施加肽类铁载体、表达该肽类铁载体的细菌或包含该肽类铁载体的组合物来促进植物生长、促进根生长或发育、提高植物的耐逆性和/或增加植物的产量的方法，以及/或通过向植物施加肽类铁载体、表达该肽类铁载体的细菌或包含该肽类铁载体的组合物来传递一氧化氮(NO)到植物和/或增强植物的叶绿素产生。