CuSer2

• 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: CuSer2
• 英文别名: Cu(serine)₂；bis(L-serinato)copper(II)；cis-bis(amino acidato)copper(II) complex of L-serine；copper;(2S)-2-amino-3-hydroxypropanoate
• 化学式: C₆H₁₂CuN₂O₆
• 分子量: 271.717
• InChiKey: SDIRSFKSTXMCRX-CEOVSRFSSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -5.89
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  173
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  CuSer2 在 聚合甲醛 作用下， 以 水 为溶剂， 生成 bis(α-hydroxymethyl-serinato)copper(II)
  参考文献：
  名称：

  氨基酸与金属离子配位的反应。第1部分。甲醛和金属配位的甘氨酸缩合反应的研究

  摘要：

  研究了甲醛与与Co III，Cu II和Ni II配位的甘氨酸或甘氨酸席夫碱的缩合反应。反应总是导致α-羟甲基丝氨酸。讨论了金属离子，配合物的电荷，pH和反应物比例的影响，以及席夫碱形成的影响。对于[Cu（glyO）2 ]（glyO =甘氨酸盐），甲醛在α-碳原子上的缩合先于氨基上的缩合，然后环化生成恶唑烷型环。在[Co（en）2（glyO）] 2+（en =乙二胺）的情况下，尚未获得这种机制的证据。

  DOI：

  10.1039/dt9800001655
• 作为产物：
  描述：

  L-丝氨酸 、 copper dichloride 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 CuSer2
  参考文献：
  名称：

  Synthesis, Characterization and Antimicrobial Studies of Coordination Compounds of L-Serine and their Mixed Ligand Complexes with Aspartic Acid

  摘要：

  合成并表征了 Co(II)、Ni(II) 和 Cu(II) 与 L-丝氨酸及其与 L-天冬氨酸的混合配体的配位配合物。利用紫外-可见光谱、红外光谱和金属分析对这些化合物进行了表征。对复合物进行了抗菌研究，受试微生物包括两种革兰氏阳性菌、五种革兰氏阴性菌和一种真菌。研究结果表明，L-天冬氨酸和 L-丝氨酸作为三叉配体的配合物具有八面体几何结构。配体分别通过 N 和 O 供体原子与金属离子配位。抗菌研究表明，这些配合物对微生物具有活性。

  DOI：

  10.14233/ajchem.2017.20203

文献信息

• Reactions of a series of bis(α-amino acidato)copper(<scp>ii</scp>) complexes with formaldehyde and benzamide: aldol-type condensation versus Mannich aminomethylation
  作者：Chew Hee Ng、Thiam Seong Chong、Siang Guan Teoh、Farook Adams、Seik Weng Ng

  DOI：10.1039/b202955c

  日期：——

  In the reactions of bis(α-amino acidato)copper(II) with formaldehyde and benzamide, competing processes occur and the preferred pathway depends on the nature and number of the α-carbon substituents of the chelated amino acid, and the pH of the reaction medium. Aldol-type condensation yields complexes with oxazolidine ring(s) while Mannich aminomethylation results in the formation of complexes with N-methylbenzamido pendant arm(s). The crystal structure determination of bis(3-methylbenzamido-5-methyloxazolidine-4-carboxylato)copper(II) dihydrate establishes its formation from a combination of both processes, in which aldol condensation occurs first. The chemistry of these reactions is rationalized with a proposed reaction scheme. The synthesized compounds are characterized by infrared spectroscopy and microanalysis.

  在双（α-氨基酸）铜（II）与甲醛和苯甲酰胺的反应中，会发生竞争过程，首选途径取决于螯合氨基酸的α-碳取代基的性质和数量以及pH值反应介质的。羟醛型缩合产生与恶唑烷环的复合物，而曼尼希氨甲基化导致与N-甲基苯甲酰氨基侧臂形成复合物。双(3-甲基苯甲酰胺基-5-甲基恶唑烷-4-羧基)铜(II)二水合物的晶体结构测定确定其形成过程是两个过程相结合的过程，其中羟醛缩合首先发生。这些反应的化学反应通过所提出的反应方案进行了合理化。通过红外光谱和微量分析对合成的化合物进行了表征。
• A polarimetric study of the reaction of bis(L-serinato)copper(II) with formaldehyde
  作者：Soon-Beng Teo、Max J. O'Connor

  DOI：10.1016/s0020-1693(00)80066-3

  日期：1984.5

  Abstract Polarimetric data have shown that the base-catalyzed reaction of bis(L-serinato)copper(II) with excess formaldehyde proceeds via the initial dissociation of the proton on the nitrogen atom of the amino acid chelate. A bis(oxazolidine)copper(II) complex appears as an intermediate but this species is not detected polarimetrically at 50°C and above.

  摘要极化数据表明，双（L-丝氨酸）铜（II）与过量甲醛的碱催化反应是通过质子在氨基酸螯合物的氮原子上的初始解离而进行的。双（恶唑烷）铜（II）络合物作为中间体出现，但在50°C及更高温度下未用旋光法检测到。
• Dual-Stimuli-Responsive <scp>l</scp>-Serine-Based Zwitterionic UCST-Type Polymer with Tunable Thermosensitivity
  作者：Tanmoy Maji、Sanjib Banerjee、Yajnaseni Biswas、Tarun K. Mandal

  DOI：10.1021/acs.macromol.5b01099

  日期：2015.7.28

  in this pH range, the two-phase PSA solution becomes one-phase upon heating, exhibiting distinct reversible upper critical solution temperature (UCST)-type phase transition. The cloud point (Tp) is found to increase with increasing molecular weights of PSAs. It is also observed that the Tp changes with changing the solution pH, exhibiting highest Tp near the isoelectric point of PSA. Addition of an

  合成升基于丝氨酸的两性离子聚合物，聚（升描述了在70°C的水中通过可逆的加成-断裂链转移（RAFT）聚合可控制的分子量和低多分散性的丙烯酸丝氨酸酯（PSA）。所获得的均聚物PSA对水溶液中的pH和温度表现出双重响应。所述PSA在pH 2.85附近表现出等电点，其中PSA分子以其两性离子形式存在。在2.3-3.5的pH范围内，由于相邻两性离子PSA分子的侧铵和羧酸根之间的分子内和分子间静电相互作用形成不溶性聚集体，因此PSA水溶液显示为两相体系。此外，在该pH范围内，两相PSA溶液在加热时变为一相，表现出独特的可逆的上临界溶液温度（UCST）型相变。浊点（发现T p）随着PSA分子量的增加而增加。还观察到T p随着溶液pH的变化而变化，在PSA的等电点附近表现出最高的T p。在抗聚电解质作用后，添加电解质（如盐水溶液）也会影响PSA溶液的T p。最后，通过对PSA侧基的后氨基进行后修饰，制备
• Copper complexes for biomedical applications: Structural insights, antioxidant activity and neuron compatibility
  作者：Ladan Esmaeili、Mariela Gomez Perez、Maziar Jafari、Joanne Paquin、Pompilia Ispas-Szabo、Veronica Pop、Marius Andruh、Joshua Byers、Mircea Alexandru Mateescu

  DOI：10.1016/j.jinorgbio.2018.12.010

  日期：2019.3

  Copper coordinated with amino acid residues is essential for the function of many proteins. In addition, copper complexed to free L-Histidine, as [Cu(His)(2)], is used in the treatment of the neurodegenerative Menkes disease and of cardioencephalomyopathy. This study was aimed to coordinate copper(II) with four small ligands (L. Serine, L-Histidine, Urea and Biuret) and to evaluate structural features, stability, antioxidant activity and neuronal compatibility of the resulting complexes. All complexes were synthesized with CuCl2 and purified by precipitation in alcohol. Elemental composition, X-rays diffraction and FTIR indicated that the complexes were in form of [Cu(ligand)(2)] and exhibited tridentate (L-Histidine), bidentate (L-Serine and Biuret) or monodentate (Urea) coordination with copper. UV Vis absorbance profiles in physiologically relevant solutions and cyclic voltammetry revealed that, contrarily to [Cu(Urea)(2)Cl-2] and (Cu(Biuret)(2)Cl-2], the [Cu(Ser)(2)] and [Cu(His)(2)Cl-2] complexes were stable in different media including water, physiological saline and intestinal-like solutions. All complexes and their ligands had antioxidant capacity as evaluated by DPPH (1,1-diphenyl-2,2-picrylhydrazyl) and DPD (N,N-diethyl-p-phenylenediamine) methods, and the [Cu(His)(2)Cl-2] complex was the most potent. Neuronal compatibility was assessed through cell viability measurements using cultured neurons derived from mouse P19 stem cells. Although only [Cu(His)(2)Cl-2] showed a good neurocompatibility (about 90% at concentrations up to 200 mu M), the cytotoxicity of the other copper complexes was lower compared to equivalent concentrations of CuCl2. These findings open new perspectives for the use of these copper complexes as antioxidants and possibly as therapeutic agents for neurodegenerative diseases. Furthermore, study of these complexes may help to improve chelation therapy for copper dysfunctions.
• Effect of different α-substituents on the Mannich reaction of copper(II) chelated α-amino acids with formaldehyde and acetamide: X-ray structure of aquabis(3-methylacetamido-5-methyl-oxazolidine-4-carboxylato)-copper(II)
  作者：Chew Hee Ng、Yih Tong Lim、Norhayati Moris、Siang Guan Teoh

  DOI：10.1016/s0277-5387(02)01434-1

  日期：2003.2

  The reactions of a series of bis(alpha-substituted glycinato)copper(II) complexes, Cu(aa)(2), with formaldehyde and acetamide have been carried out. For Cu(aa)(2) with an activating alpha-alkyl or reactive alpha-hydroxyalkyl substituent, they undergo both aldol-type condensation and Mannich aminomethylation to yield complexes with an oxazolidine-ring and one methylacetamido pendant. The crystal structure of one of these complexes is reported. The Cu(aa)(2) with a non-activating alpha-alkyl substituent is diacetamidomethylated. A proposed mechanism to account for the above differences and an analysis of thermal decomposition data of the two types of complexes are further described. (C) 2003 Elsevier Science Ltd. All rights reserved.