N²-benzyloxycarbonyl-N⁵-hydroxy-L-ornithine | 762227-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N²-benzyloxycarbonyl-N⁵-hydroxy-L-ornithine
• 英文别名: (2S)-5-(hydroxyamino)-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 762227-03-2
• 化学式: C₁₃H₁₈N₂O₅
• 分子量: 282.296
• InChiKey: YPWPPWKKEWGQFD-NSHDSACASA-N

物化性质

• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N²-benzyloxycarbonyl-N⁵-hydroxy-L-ornithine 在 盐酸 、 potassium acetate 、 potassium hydrogencarbonate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 N²-benzyloxycarbonyl-N⁵-acetyl-N⁵-hydroxy-L-ornithine DIPEA salt
  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 在 间氯过氧苯甲酸 、 三氟乙酸 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 N²-benzyloxycarbonyl-N⁵-hydroxy-L-ornithine
  参考文献：
  名称：

  [EN] ANTIBODY DRUG CONJUGATES
  [FR] CONJUGUÉS ANTICORPS-MÉDICAMENT

  摘要：

  本发明涉及一种抗体-药物结合物，其包括抗体、铁离子和至少一种药物分子，并涉及一种包括抗体-药物结合物的制药组合物。本发明还涉及使用抗体-药物结合物治疗疾病，例如癌症。

  公开号：

  WO2018095891A1

文献信息

• Elucidation of Chalkophomycin Biosynthesis Reveals N-Hydroxypyrrole-Forming Enzymes
  作者：Anne Marie Crooke、Anika K. Chand、Zheng Cui、Emily P. Balskus

  DOI：10.1021/jacs.4c04712

  日期：2024.6.12

  C-type diazeniumdiolate and N-hydroxypyrrole. Characterizing chalkophomycin biosynthetic enzymes reveals previously unknown enzymes responsible for N-hydroxypyrrole biosynthesis, including the first prolyl-N-hydroxylase, and a key step in the assembly of the diazeniumdiolate-containing amino acid graminine. Discovery of this pathway enriches our understanding of the biosynthetic logic employed in constructing

  反应性官能团，例如N-亚硝胺，赋予它们所在的天然产物独特的生物活性。最近的工作阐明了微生物天然产物生物合成中的酶促N-亚硝化反应，激发了人们对发现利用这种反应性构建的其他代谢物的兴趣。在这里，我们使用基因组挖掘方法来识别超过 400 个编码N 亚硝化生物合成酶 SznF 同源物的隐性生物合成基因簇 (BGC)，包括 Chalkopomycin 的 BGC，这是一种 Cu II结合代谢物，含有C型二氮烯鎓二醇和N-羟基吡咯。对查克霉素生物合成酶的表征揭示了以前未知的负责N-羟基吡咯生物合成的酶，包括第一个脯氨酰-N-羟化酶，以及含有二醇二氮烯鎓的氨基酸禾谷胺组装的关键步骤。该途径的发现丰富了我们对构建不寻常的杂原子-含杂原子键的官能团所采用的生物合成逻辑的理解，从而使未来在天然产物发现和生物催化方面的努力成为可能。
• Genomics‐Driven Discovery of NO‐Donating Diazeniumdiolate Siderophores in Diverse Plant‐Associated Bacteria
  作者：Ron Hermenau、Jule L. Mehl、Keishi Ishida、Benjamin Dose、Sacha J. Pidot、Timothy P. Stinear、Christian Hertweck

  DOI：10.1002/anie.201906326

  日期：2019.9.9

  AbstractSiderophores are key players in bacteria–host interactions, with the main function to provide soluble iron for their producers. Gramibactin from rhizosphere bacteria expands siderophore function and diversity as it delivers iron to the host plant and features an unusual diazeniumdiolate moiety for iron chelation. By mutational analysis of the grb gene cluster, we identified genes (grbD and grbE) necessary for diazeniumdiolate formation. Genome mining using a GrbD‐based network revealed a broad range of orthologous gene clusters in mainly plant‐associated Burkholderia/Paraburkholderia species. Two new types of diazeniumdiolate siderophores, megapolibactins and plantaribactin were fully characterized. In vitro assays and in vivo monitoring experiments revealed that the iron chelators also liberate nitric oxide (NO) in plant roots. This finding is important since NO donors are considered as biofertilizers that maintain iron homeostasis and increase overall plant fitness.