cyclotri(N⁵-acetyl-N⁵-hydroxy-L-ornithylglycyl) | 107442-99-9

• 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: cyclotri(N⁵-acetyl-N⁵-hydroxy-L-ornithylglycyl)
• 英文别名: cyclo(-(N^δ-acetyl-N^δ-hydroxy-L-ornithine)-Gly-(N^δ-acetyl-N^δ-hydroxy-L-ornithine)-Gly-(N^δ-acetyl-N^δ-hydroxy-L-ornithine)-Gly-)；N-[3-[(2S,8S,14S)-8,14-bis[3-[acetyl(hydroxy)amino]propyl]-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-hydroxyacetamide
• CAS: 107442-99-9
• 化学式: C₂₇H₄₅N₉O₁₂
• 分子量: 687.707
• InChiKey: ZPYIPEIWDLBSDO-ACRUOGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.14
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  296.22
• 氢给体数：
  9.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine 在 palladium on activated charcoal N-甲基吗啉 、 吡啶 、 sodium hydroxide 、 N-羟基丁二酰亚胺 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 167.5h， 生成 cyclotri(N⁵-acetyl-N⁵-hydroxy-L-ornithylglycyl)
  参考文献：
  名称：

  N-Hydroxy amides. 7. Synthesis and properties of linear and cyclic hexapeptides containing three N5-acetyl-N5-hydroxy-L-ornithine residues as models for ferrichrome

  摘要：

  DOI：

  10.1021/jo00261a019

文献信息

• Synthesis and functional analysis of deferriferrichrysin derivatives: Application to colorimetric pH indicators
  作者：Yuka Kobayashi、Shinya Oishi、Kazuya Kobayashi、Hiroaki Ohno、Hiroko Tsutsumi、Yoji Hata、Nobutaka Fujii

  DOI：10.1016/j.bmc.2013.04.078

  日期：2013.7

  Deferriferrichrysin belongs to the siderophore peptide family which are Fe(III)-coordinating cyclic peptides. The common structure of this family is three consecutive hydroxamate moieties, such as N-delta-acetyl-N-delta-hydroxy-L-ornithine (Aho). We have designed two deferriferrichrysin derivatives where three Aho residues were arranged as: cyclo(-Aho-Gly-Aho-Gly-Aho-Gly-) and cyclo(-Aho-Ser-Aho-Ser-Aho-Ser-). Comparative evaluation of the physicochemical properties of their Fe(III) complexes revealed that naturally occurring deferriferrichrysin formed a more stable Fe(III) complex when compared with the two derivatives. This result shows that three consecutive Aho residues are indispensable for high affinity Fe(III) binding by deferriferrichrysin. Of note, the observed pH-dependent chromogenic response of the Fe(III) complexes of the derivatives suggests that these two derivatives should function as sensitive pH indicators in acidic environments. (C) 2013 Elsevier Ltd. All rights reserved.
• AKIYAMA, MASAYASU;KATOH, AKIRA;MUTOH, TSUTOMU, J. ORG. CHEM., 53,(1988) N6, C. 6089-6094
  作者：AKIYAMA, MASAYASU、KATOH, AKIRA、MUTOH, TSUTOMU

  DOI：——

  日期：——