1,3-bis-(N-succinimidyl) 2-tert-butyl citrate | 114340-53-3

• 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: 1,3-bis-(N-succinimidyl) 2-tert-butyl citrate
• 英文别名: 2-tert-butyl-1,3-di-N-(hydroxy)succinimidyl citrate；2-tert-butyl-1,3-di-N-(hydroxyl) succinimidyl citrate；2-O-tert-butyl 1-O,3-O-bis(2,5-dioxopyrrolidin-1-yl) 2-hydroxypropane-1,2,3-tricarboxylate
• CAS: 114340-53-3
• 化学式: C₁₈H₂₂N₂O₁₁
• 分子量: 442.379
• InChiKey: OLFFOQNGXMMYBM-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  599.8±60.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  174
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,3-bis-(N-succinimidyl) 2-tert-butyl citrate 在 sodium hydroxide 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.08h， 生成 丁酸,2-羟基-4-[[3-[羟基[(2E)-1-羰基-2-辛烯-1-基]氨基]丙基]氨基]-2-[2-[[3-[羟基[(2E)-1-羰基-2-辛烯-1-基]氨基]丙基]氨基]-2-羰基乙基]-4-羰基-
  参考文献：
  名称：

  Schizokinen 和两亲性铁载体 Acinetoferrin 镓配合物的合成、结构和分子动力学

  摘要：

  描述了一种新的基于柠檬酸盐的铁载体 acinetoferrin (Af) 和 schizokinen (Sz) 及其类似物的一般合成。GaSz 的分子结构由 (1) H NMR、Hartree-Fock ab initio 计算、DFT 和邻位质子 NMR 自旋-自旋耦合的经验建模确定。GaSz 的金属配位几何结构由 NOE 接触确定，相对于两种螯合异羟肟酸盐是顺-顺。一种二氨基丙烷采用单一的椅子状构象，而另一种是两种环状褶皱排列的混合物。两个酰胺氢在内部都是与金属配位氧原子键合的氢。酰基甲基以大约约 2 的平均平面角相互远离。130度。GaSz 外消旋化的动力学遵循选择性，双自旋回波反转恢复 (1) H NMR 光谱在 10-45 摄氏度的温度范围内。外消旋化通过多步机制进行，该机制在 pD 5 和 12 之间独立于质子 (k(0) = 1.47 (0.15 s) (-1))) 和酸催化低于

  DOI：

  10.1021/ja048145j
• 作为产物：
  描述：

  tert-butyl-1,5-dimethyl citrate 在 sodium hydroxide 、 达卡巴嗪 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 51.0h， 生成 1,3-bis-(N-succinimidyl) 2-tert-butyl citrate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Citrate-Based Siderophores as Potential Probes for the Mechanism of Iron Uptake in Mycobacteria

  摘要：

  Several iron chelators containing alpha,beta-unsaturated hydroxamic acid motifs appended to a citric acid platform were synthesized. Mycobacterium paratuberculosis was then challenged to grow in the presence of a panel of siderophores (mycobactin J, deferrioxamine B, acinetoferrin, and nannochelin A) and the new synthetic agents. Of the structures tested, those containing the trans 2-octenoyl motif were preferred over those with trans cinnamoyl groups. In addition, derivatives containing longer tether lengths between the iron binding ligands (C5) were more efficacious and led to higher growth index values. Perhaps most remarkable was the finding that at 2.4 muM a trans 2-octenoylated, citrate-containing imide 6 was nearly 5-fold more effective in stimulating growth than the native chelator, mycobactin J. In this regard, new structural elements were identified (e.g., an imide motif or 2-octenoyl side chain), whose presence stimulated mycobacterial growth.

  DOI：

  10.1021/jm0104522

文献信息

• Total Synthesis of Petrobactin and Its Homologues as Potential Growth Stimuli for <i>Marinobacter </i><i>h</i><i>ydrocarbonoclasticus</i>, an Oil-Degrading Bacteria
  作者：Richard Andrew Gardner、Rebecca Kinkade、Chaojie Wang、Phanstiel

  DOI：10.1021/jo049803l

  日期：2004.5.1

  in M. hydrocarbonoclasticus. The synthesis of petrobactin and its homologues and the first biological study of how these agents influence the growth of Mycobacter hydrocarbonoclasticus are reported. New synthetic methods were developed to overcome issues (imide formation) encountered in earlier syntheses. Both the 1H and 13C NMR of petrobactin were consistent with the recently revised structure showing

  一种模块化合成的开发是为了访问petrobactin，含儿茶酚铁载体分离自Marinobacter hydrocarbonoclasticus。还合成了一系列具有不同二羟基苯甲酰胺基序的石油robactin同源物，在一种情况下，还合成了多胺主链中增加的碳数。因此，这些系统代表了新的异构探针，用于研究碳氢解质支原体中铁的运输性质。报道了石油链菌素及其同系物的合成以及这些药剂如何影响烃裂枝分枝杆菌的生长的首次生物学研究。开发了新的合成方法来克服早期合成中遇到的问题（酰亚胺形成）。两者都1石蜡肌动蛋白的1 H和13 C NMR与最近修订的结构一致，表明该石蜡肌动蛋白实际上包含3,4-二羟基苯基序而不是2,3-二羟基苯基序。初步的生物研究表明，使用本机petrobactin 1B为M. hydrocarbonoclasticus特异性生长刺激可能对溢油清理一个贫穷的战略。
• Utilizing an iron(<scp>iii</scp>)-chelation masking strategy to prepare mono- and bis-functionalized aerobactin analogues for targeting pathogenic bacteria
  作者：Yu-Hin Ho、Sheng-Yang Ho、Cheng-Chih Hsu、Jiun-Jie Shie、Tsung-Shing Andrew Wang

  DOI：10.1039/c7cc05197b

  日期：——

  We present a facile functionalization of native siderophoresviaan Fe(iii)-chelation masking strategy to prepare fluorophore conjugates for targeting pathogenic bacteria.

  我们提出了一种简便的方法，通过Fe（III）螯合掩蔽策略对天然铁载体进行功能化，以制备荧光染料共轭物，用于针对致病菌的靶向。
• Efficient synthesis of the siderophore petrobactin via antimony triethoxide mediated coupling
  作者：Rajesh K. Pandey、Gregory G. Jarvis、Philip S. Low

  DOI：10.1016/j.tetlet.2012.01.074

  日期：2012.3

  Chemical synthesis of petrobactin, a siderophore for Bacillus anthracis, has been achieved via Sb(OEt)(3)-mediated ester-amide exchange. (C) 2012 Elsevier Ltd. All rights reserved.
• Milewska, Maria J.; Chimiak, Andrzej; Neilands, John B., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1991, vol. 46, # 1, p. 117 - 122
  作者：Milewska, Maria J.、Chimiak, Andrzej、Neilands, John B.

  DOI：——

  日期：——
• Synthesis and biological activities of flavolipids
  作者：Samiul M. Ahad、Alison L. Ange、Robert B. Bates、Bonnie L. Bell、Adria A. Bodour、Bryan R. Bourne、Cristina G. Contreras、Emily L. Goldberg、A.A. Leslie Gunatilaka、Sheryl King、Albert K. Lee、Rebecca L. Low、Raina M. Maier、Kathryn M. Marlor、Marilyn T. Marron、Ryan C. Scolnik、Matthew J. Streeter、Malgorzata Strelczuk、Long N. Trinh、Vu K. Truong、Sage P. Vissering、Megan C. Weick、Maria T. Williams

  DOI：10.1016/j.tet.2010.09.088

  日期：2010.11

  Syntheses of the bacterial surfactants 6S 6S- 9S 9S- and 9U 9U-flavolipids confirmed the structures proposed for them from spectroscopic analysis of a flavolipid mixture and made pure flavolipids available for the first time All three synthetic flavolipids and a straight chain analogue were found to be weakly cytotoxic and to inhibit metastatic cancer cell migration with 9U 9U-fiavolipid (the most abundant natural flavolipid) having the most activity Biosynthetic routes to the branched side-chains of the flavolipids are suggested and it is proposed that branched chains are employed to hinder biodegradation (C) 2010 Elsevier Ltd All rights reserved