N⁵-Acetyl-N⁵-hydroxyornithin | 37552-50-4

• 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: N⁵-Acetyl-N⁵-hydroxyornithin
• 英文别名: δ-N-Ac-δ-N-hydroxy-Orn；N-Acetyl-N-hydroxiornithin；5-[acetyl(hydroxy)amino]-2-azaniumylpentanoate
• CAS: 37552-50-4
• 化学式: C₇H₁₄N₂O₄
• 分子量: 190.199
• InChiKey: LUZHSHCYVQASCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-5-(Acetyl-benzoyloxy-amino)-2-benzyloxycarbonylamino-pentanoic acid tert-butyl ester 在 palladium on activated charcoal 氨 、 氢气 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 3.33h， 生成 N⁵-Acetyl-N⁵-hydroxyornithin
  参考文献：
  名称：

  An Alternative Synthesis ofN ⁵-Acetyl-N ⁵-hydroxy-L-ornithine from L-Ornithine

  摘要：

  通过过氧化二苯甲酰基氧化 N 2-苄氧羰基-L-鸟氨酸叔丁酯中的Ï-氨基基团，然后进行 N 5-乙酰化，可从 L-鸟氨酸中获得 N 5-乙酰基-N 5-羟基-L-鸟氨酸，总产率为 20%。

  DOI：

  10.1055/s-1990-26840

文献信息

• Acylation of<i>N</i>^δ-Benzyloxyornithine
  作者：Yoshikazu Isowa、Toshiyuki Takashima、Muneki Ohmori、Hideaki Kurita、Masanari Sato、Kaoru Mori

  DOI：10.1246/bcsj.45.1464

  日期：1972.5

  the other hand, acetylation or alkoxycarbonylation of Nδ-benzyloxyornithine(I) proceeded through Nα-acetylation, followed by spontaneous cyclization to form lactams, which yielded cyclic hydroxamic acids on catalytic reduction. These hydroxamic acid and Nδ-acetyl-Nδ-hydroxyornithine were readily hydrolyzed to give Nδ-hydroxyornithine.

  Nδ-苄氧基鸟氨酸单氢溴酸盐 (I·HBr) 与乙酸酐乙酰化得到 Nδ-乙酰化产物，通过催化还原生成 Nδ-乙酰基-Nδ-羟基鸟氨酸。另一方面，Nδ-苄氧基鸟氨酸(I)的乙酰化或烷氧基羰基化通过Nα-乙酰化进行，然后自发环化形成内酰胺，催化还原生成环状异羟肟酸。这些异羟肟酸和Nδ-乙酰基-Nδ-羟基鸟氨酸很容易水解得到Nδ-羟基鸟氨酸。
• Albomycine, I Enzymatische Spaltung der Desferriform der Albomycine δ1, δ2
  作者：Günter Benz

  DOI：10.1002/jlac.198419840802

  日期：1984.8.10

  Enzymatische Hydrolyseversuche an Albomycin δ2 (1a) werden mit 23 Enzymen oder Enzymgemischen durchgeführt. 1a und Albomycin δ1 (1b) werden mit Leucinaminopeptidase (mikrosomal, Schweineniere), Subtilisin, Aminoacylase I, β-Lactamase, Proteinase K und Pronase E zu den serinhaltigen Nucleosiden 3a und b gespalten. Mit der mikrosomalen Leucinaminopeptidase erfolgt eine Weiterreaktion zu den serinfreien

  上白霉素δ酶水解实验2（1A）与23倍的酶或酶进行的混合物。图1A和白霉素δ 1（图1b）的切割用亮氨酸氨肽（微粒体，猪肾脏），枯草杆菌蛋白酶，酰化氨基酸水解酶I，β内酰胺酶，蛋白酶K和链霉蛋白酶E，形成含有丝氨酸核苷3A和b。微粒体亮氨酸氨基肽酶与不含丝氨酸的核苷4a和b发生进一步反应。异羟肟酸6也可以以纯净形式分离。
• Biologically active peptides TAN-866
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0253245B1

  公开（公告）日：1992-10-14
• METHODS FOR TARGET MOLECULE DETECTION USING SIDEROPHORES AND RELATED COMPOSITIONS
  申请人：PerkinElmer LAS, Inc.

  公开号：EP1766076A2

  公开（公告）日：2007-03-28
• Inhibitors of Siderophore Biosynthesis in Fungi
  申请人：Haas Hubertus

  公开号：US20080152641A1

  公开（公告）日：2008-06-26

  The present invention relates to methods for screening inhibitors of siderophore biosynthesis in fungi, preferably in Aspergillus species, particularly preferred in Aspergillus fumigatus comprising (a) contacting a cell expressing a fungal siderophore with a compound to be tested; (b) determining whether said cell is capable of siderophore biosynthesis in the presence of said compound to be tested when compared to a cell not contacted with said compound; and (c) identifying the compound which inhibits fungal siderophore biosynthesis. Accordingly, the invention also provides for a method for screening inhibitors of fungal siderophore biosynthesis comprising the steps of (a) contacting an enzyme involved in siderophore biosynthesis with a compound to be tested; (b) determining whether said enzyme is functional in the pathway of siderophore biosynthesis in the presence of said compounds to be tested when compared to an enzyme not contacted with said compound; and (c) identifying the compound which inhibits the enzymatic function involved in siderophore biosynthesis. In another aspect the present invention relates to a method of preparing a pharmaceutical composition for treating diseases associated with fungal infections, particularly, aspergillosis or coccidiosis comprising (a) identifying a compound which inhibits fungal siderophore biosynthesis; and (b) formulating said compound with a pharmaceutically acceptable carrier. In a further aspect, the present invention relates to a method for the production of a pharmaceutical composition comprising the steps of the aforementioned screening method and the subsequent step of mixing the compound identified to be an inhibitor of fungal siderophore biosynthesis with a pharmaceutically acceptable carrier. Moreover, the present invention envisages a pharmaceutical composition comprising an inhibitor of fungal siderophore biosynthesis as well as the use of such an inhibitor for the preparation of a pharmaceutical composition for the prevention and/or treatment of diseases associated with fungal infections, particularly, aspergillosis or coccidiosis.