tert-butyl-1,5-dimethyl citrate | 114340-51-1

• 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: tert-butyl-1,5-dimethyl citrate
• 英文别名: 2-tert-butyl 1,3-dimethyl 2-hydroxypropane-1,2,3-tricarboxylate；dimethyl 3-(tert-butoxycarbonyl)-3-hydroxypentanedioate；3-tert-butyl 1,5-dimethyl citrate；2-O-tert-butyl 1-O,3-O-dimethyl 2-hydroxypropane-1,2,3-tricarboxylate
• CAS: 114340-51-1
• 化学式: C₁₂H₂₀O₇
• 分子量: 276.287
• InChiKey: PWSGVJPWIKGYHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  284.4±7.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl-1,5-dimethyl citrate 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 碳酸氢钠 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 4-[3-(乙酰基-羟基氨基)丙基氨基]-2-[2-[3-(乙酰基-羟基氨基)丙基氨基]-2-氧代乙基]-2-羟基-4-氧代丁酸
  参考文献：
  名称：

  Milewska, Maria J.; Chimiak, Andrzej; Glowacki, Zdzislaw, Journal fur praktische Chemie (Leipzig 1954), 1987, vol. 329, # 3, p. 447 - 456

  摘要：

  DOI：
• 作为产物：
  描述：

  柠檬酸 在 高氯酸 、 硫酸 作用下， 反应 73.0h， 生成 tert-butyl-1,5-dimethyl citrate
  参考文献：
  名称：

  Synthesis and characterisation of tin(II) and tin(IV) citrates

  摘要：

  一系列柠檬酸亚锡（SnM(C6H4O7)）（M = Sn或Zn）和SnMM′(C6H4O7)（M = M′ = Na、K或NH4；M = NMe4，M′ = H）以及相关的1,5-二甲基和1,5-二正丁基柠檬酸单亚锡（II）盐已经合成，并通过光谱方法（IR、1H、13C、119Sn NMR、119Sn Mössbauer）进行了表征。二聚柠檬酸亚锡（II）1,5-二甲基柠檬酸盐和氧化产物Sn(NMe4)2(C6H5O7)2·3.5H2O的晶体结构也已确定。

  DOI：

  10.1039/a704511e

文献信息

• Rapid-acting insulin composition comprising a substituted citrate
  申请人：ADOCIA

  公开号：US20170136097A1

  公开（公告）日：2017-05-18

  A composition, in the form of an aqueous solution, including an insulin in hexameric form and at least one substituted citrate of formula I: in which: R 1 , R 2 , R 3 , identical or different, represent OH or AA, at least one of the R 1 , R 2 , R 3 is an AA radical, AA is a radical resulting from a natural or synthetic aromatic amino acid comprising at least one phenyl group or indole group, substituted or not substituted, said AA radical having at least one free carboxylic acid function, and the carboxylic acid functions are in the form of a salt of an alkali metal selected from Na + and K + .

  一种组合物，以水溶液的形式存在，包括六聚体形式的胰岛素和至少一种式I的取代柠檬酸盐：其中：R1、R2、R3，相同或不同，代表OH或AA，R1、R2、R3中至少有一个是AA基团，AA是由天然或合成的芳香氨基酸组成的基团，包括至少一个苯基或吲哚基，取代或未取代，所述AA基团具有至少一个自由羧酸功能基团，羧酸功能基团以Na+和K+中选择的碱金属的盐形式存在。
• Comparison of human glutamate carboxypeptidases II and III reveals their divergent substrate specificities
  作者：Michal Navrátil、Jan Tykvart、Jiří Schimer、Petr Pachl、Václav Navrátil、Tibor András Rokob、Klára Hlouchová、Lubomír Rulíšek、Jan Konvalinka

  DOI：10.1111/febs.13761

  日期：2016.7

  UNLABELLED Glutamate carboxypeptidase III (GCPIII) is best known as a homologue of glutamate carboxypeptidase II [GCPII; also known as prostate-specific membrane antigen (PSMA)], a protease involved in neurological disorders and overexpressed in a number of solid cancers. However, mouse GCPIII was recently shown to cleave β-citrylglutamate (BCG), suggesting that these two closely related enzymes have

  未标记的谷氨酸羧肽酶 III (GCPIII) 是众所周知的谷氨酸羧肽酶 II [GCPII; 也称为前列腺特异性膜抗原 (PSMA)]，一种涉及神经系统疾病并在许多实体癌中过度表达的蛋白酶。然而，最近显示小鼠 GCPIII 可裂解 β-柠檬酸谷氨酸 (BCG)，表明这两种密切相关的酶具有不同的功能。为了开发一种工具来剖析、评估和量化人类 GCPII 和 GCPIII 的活性，我们分析了这些酶对三种生理底物的催化效率。我们观察到 GCPIII 但不是 GCPII 的 BCG 裂解效率高。我们还确定了二价阳离子对 GCPIII 酶活性的强烈调节，而我们没有观察到 GCPII 的这种影响。此外，我们使用 X 射线晶体学和计算模型（量子和分子力学计算）来描述 BCG 分别与 GCPII 和 GCPIII 的活性位点结合的机制。最后，我们利用 GCPII 和 GCPIII 对其底物的酶促效率的显着
• Synthesis of Biosynthetic Intermediates of Vibrioferrin and Enzyme Reactions Using Them as Substrates
  作者：Hidemichi Mitome、Tomotaka Tanabe、Tatsuya Funahashi、Kazuki Akira

  DOI：10.1248/cpb.c24-00168

  日期：2024.6.14

  alanine-2-amidoethyl citrate were respectively synthesized as a mixture of stereoisomers. These compounds were used as substrates for enzyme reactions using recombinant PvsA, PvsB, and PvsE proteins as corresponding enzyme equivalents. The results of our study show that each enzyme reacts with a respective substrate and produces VF along the proposed biosynthetic pathway. Furthermore, the results of this study will

  分别合成了铁载体弧铁蛋白（VF）、 O-柠檬酰-L-丝氨酸、柠檬酸2-氨基乙酯和柠檬酸丙氨酸-2-氨基乙酯的生物合成中间体，作为立体异构体的混合物。这些化合物用作酶反应的底物，使用重组 PvsA、PvsB 和 PvsE 蛋白作为相应的酶等价物。我们的研究结果表明，每种酶与各自的底物发生反应，并沿着所提出的生物合成途径产生 VF。此外，这项研究的结果将有助于了解 VF 生物合成酶，并可能有助于通过抑制铁载体生物合成酶来开发抗菌药物。  全尺寸图像
• Synthesis of novel citrate-based siderophores and siderophore-.beta.-lactam conjugates. Iron transport-mediated drug delivery systems
  作者：Arun Ghosh、Marvin J. Miller

  DOI：10.1021/jo00079a007

  日期：1993.12

  The synthesis of analogs of arthrobactin (5), a microbial iron chelator, and its imide 8 are described. The differentially protected citric acid residue 31 served as the key intermediate in making conjugates having a generalized structure 14 with two representative carbacephalosporin units, 15 and 16. Both conjugates, 49 and 51, showed antibiotic activity, while conjugate 51 obtained from beta-lactam 16 bearing a phenylglycyl side chain was shown to be more effective.
• Synthesis and Biological Evaluation of New Citrate-Based Siderophores as Potential Probes for the Mechanism of Iron Uptake in Mycobacteria
  作者：Hongyan Guo、Saleh A. Naser、George Ghobrial、Phanstiel

  DOI：10.1021/jm0104522

  日期：2002.5.1

  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.