N²-benzyloxycarbonyl-N⁵-(3-phenyloxaziridinyl)-L-ornithine | 250215-08-8

• 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-(3-phenyloxaziridinyl)-L-ornithine
• 英文别名: (2S)-2-(phenylmethoxycarbonylamino)-5-(3-phenyloxaziridin-2-yl)pentanoic acid
• CAS: 250215-08-8
• 化学式: C₂₀H₂₂N₂O₅
• 分子量: 370.405
• InChiKey: LSIPZISICJLLTD-LYGNXSNRSA-N

物化性质

• 密度：
  1.287±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N²-benzyloxycarbonyl-N⁵-(3-phenyloxaziridinyl)-L-ornithine 在 盐酸 、 potassium acetate 、 potassium hydrogencarbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 5.75h， 生成 N²-benzyloxycarbonyl-N⁵-acetyl-N⁵-O-acetyl-L-ornithine
  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 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 N²-benzyloxycarbonyl-N⁵-(3-phenyloxaziridinyl)-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] ANTIBODY DRUG CONJUGATES<br/>[FR] CONJUGUÉS ANTICORPS-MÉDICAMENT
  申请人：HOFFMANN LA ROCHE

  公开号：WO2018095891A1

  公开（公告）日：2018-05-31

  The present invention pertains to an antibody-drug conjugate comprising an antibody, ferric iron and at least one drug molecule,and to a pharmaceutical composition comprising the antibody-drug conjugate. The invention further relates to the use of the antibody-drug conjugates in the treatment of diseases, e.g. cancer.

  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。
• Practical Synthesis of Hydroxamate-Derived Siderophore Components by an Indirect Oxidation Method and Syntheses of a DIG−Siderophore Conjugate and a Biotin−Siderophore Conjugate
  作者：Yun-Ming Lin、Marvin J. Miller

  DOI：10.1021/jo990769y

  日期：1999.10.1

  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.
• 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(<scp>iv</scp>)
  作者：Pawel Jewula、Jean-Claude Chambron、Marie-José Penouilh、Yoann Rousselin、Michel Meyer

  DOI：10.1039/c4ra00977k

  日期：——

  K⁺ is encapsulated by 2 : 2 complexes of tetravalent zirconium or hafnium with the calix[4]arene podand 1H₄ carrying four cyclic hydroxamate binding units.

  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。