(S)-α-alaninehydroxamic acid | 2508-25-0

• 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: (S)-α-alaninehydroxamic acid
• 英文别名: L-α-alaninehydroxamic acid；α-alanine hydroxamic acid；L-alaninehydroxamic acid；alaninehydroxamic acid；L-alanine hydroxamate；(S)-α-Alaha；(2S)-2-amino-N-hydroxypropanamide
• CAS: 2508-25-0
• 化学式: C₃H₈N₂O₂
• 分子量: 104.109
• InChiKey: BAAQJFBTHFOHLY-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-α-alaninehydroxamic acid 、 乙酰丙酸 以 甲苯 为溶剂， 反应 5.0h， 以49%的产率得到(3S,7aR)-1-hydroxy-3,7a-dimethyldihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)dione
  参考文献：
  名称：

  Enantiomerically Enriched Bicyclic Hydroxamic Acids in One Step from α-Aminohydroxamic Acids and Keto Acids via Cyclocondensation

  摘要：

  New enantiomerically enriched bicyclic hydroxamic acids, 1-hydroxy-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, have been synthesized by the cyclocondensation of L--aminohydroxamic acids with keto acids in a highly chemo- and stereoselective manner. The cis configuration between the amino acid side chain and the methyl group at C7a in 1H-pyrrolo[1,2-a]imidazole-2,5-dione was unambiguously established by X-ray crystallographic analysis. This method could also be applied to the cyclocondensation with o-formylbenzoic acid, giving a tricyclic hydroxamic acid in a good yield. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.717162
• 作为产物：
  描述：

  L-丙氨酰胺 在 羟胺 作用下， 以 aq. buffer 为溶剂， 反应 3.5h， 生成 (S)-α-alaninehydroxamic acid
  参考文献：
  名称：

  固定化铜绿假单胞菌细胞产生异羟肟酸：反胶束动力学分析

  摘要：

  来自铜绿假单胞菌菌株L10的含有酰胺酶的完整细胞被用作游离和固定在反胶束系统中的生物催化剂。在两种介质中，使用诸如脂肪族，氨基酸，芳香族酰胺和酯等底物，确定了异羟肟酸合成中氨基转移反应的表观动力学常数。反胶束，K m相对于以乙酰胺，丙烯酰胺，丙酰胺和甘氨酰胺乙酯为底物的游离生物催化剂，该值降低了2-7倍。我们已经得出结论，当在相反的胶束系统（而不是缓冲液系统）中进行反应时，生物催化剂对每种底物的亲和力总体上会增加。相对于游离形式，固定化的生物催化剂通常在较低的底物浓度下显示出更高的稳定性和更快的反应速率，这是有利的。另外，固定化显示适合于获得最高产率的异羟肟酸衍生物，在某些情况下高于80％。

  DOI：

  10.1016/j.molcatb.2013.03.016

文献信息

• The peculiar behavior of Picha in the formation of metallacrown complexes with Cu(<scp>ii</scp>), Ni(<scp>ii</scp>) and Zn(<scp>ii</scp>) in aqueous solution
  作者：Luciano Marchiò、Nicola Marchetti、Corrado Atzeri、Valentina Borghesani、Maurizio Remelli、Matteo Tegoni

  DOI：10.1039/c4dt03264k

  日期：——

  metallacrown complexes formed by picolinehydroxamic acid (Picha) with Cu(II), Ni(II) and Zn(II) in aqueous solution has been determined by potentiometry, and the speciation models were validated by ESI-MS and UV-visible spectrophotometry. Cu(II) and Zn(II) form 12-MC-4 species as the unique metallacrowns present in the solution. While for Cu(II) the 12-MC-4 is slightly less stable than that obtained with alaninehydroxamic

  用电位滴定法测定了甲基吡啶甲基异羟肟酸（Picha）与Cu（II），Ni（II）和Zn（II）在水溶液中形成的金属漆配合物的热力学稳定性，并通过ESI-MS和UV验证了形态模型。可见分光光度法。Cu（II）和Zn（II）形成12-MC-4物种，因为溶液中存在独特的金属漆。尽管对于Cu（II），12-MC-4的稳定性比用丙氨酸异羟肟酸（Alaha）所获得的稳定度稍差，但对Zn（II）则相反。此外，在ESI-MS条件下，使用Cu（II）可以鉴定出前所未有的15-MC-5和18-MC-6物种。Picha与Ni（相比之下，II）形成15-MC-5配合物，是一种独特的金属内陷物种。还进行了从头算方法对12-MC-4配合物构架的结构研究。我们的研究结果不仅使我们合理化了Picha在与三种金属离子形成金属凹洞时的不同行为，而且使在文献中报道的使用辅助配体（如吡啶）稳定这些物种的策略的原因得以合理化。
• Synthesis, physicochemical characterization and neuroprotective evaluation of novel 1-hydroxypyrazin-2(1<i>H</i>)-one iron chelators in an <i>in vitro</i> cell model of Parkinson's disease
  作者：Frank W. Lewis、Kathleen Bird、Jean-Philippe Navarro、Rawa El Fallah、Jeremy Brandel、Véronique Hubscher-Bruder、Andrew Tsatsanis、James A. Duce、David Tétard、Samuel Bourne、Mahmoud Maina、Ilse S. Pienaar

  DOI：10.1039/d1dt02604f

  日期：——

  Iron dysregulation, dopamine depletion, cellular oxidative stress and α-synuclein protein mis-folding are key neuronal pathological features seen in the progression of Parkinson's disease. Iron chelators endowed with one or more therapeutic modes of action have long been suggested as disease modifying therapies for its treatment. In this study, novel 1-hydroxypyrazin-2(1H)-one iron chelators were synthesized

  铁失调、多巴胺耗竭、细胞氧化应激和 α-突触核蛋白错误折叠是帕金森病进展中的关键神经元病理特征。具有一种或多种治疗作用模式的铁螯合剂长期以来一直被建议作为其治疗的疾病修饰疗法。本研究合成了新型1-羟基吡嗪-2( 1H )-酮铁螯合剂，并评估了其理化性质、铁螯合能力、抗氧化能力以及在帕金森病细胞培养模型中的神经保护作用。物理化学性质（log β 、log D 7.4 、pL 0.5 ）表明这些配体穿透细胞膜并形成较弱铁络合物的能力比密切相关的 1-羟基吡啶-2(1 H )-one 更差。尽管如此，我们表明这些配体在体外针对儿茶酚胺能神经毒素 6-羟基多巴胺提供的神经保护水平与之前使用 1-羟基吡啶-2(1 H )-one 和临床使用的铁螯合剂去铁酮所观察到的神经保护水平相当。与对照相比，其中两种配体将细胞活力恢复至 ≥89%。其中两个配体被赋予了额外的酚部分，试图衍生出具有双重铁螯合/抗氧化活性的多功能螯合剂。
• Metallacrowns of Ni(<scp>ii</scp>) with α-aminohydroxamic acids in aqueous solution: beyond a 12-MC-4, an unexpected (vacant?) 15-MC-5
  作者：Dimitri Bacco、Valerio Bertolasi、Francesco Dallavalle、Lorenzo Galliera、Nicola Marchetti、Luciano Marchiò、Maurizio Remelli、Matteo Tegoni

  DOI：10.1039/c0dt00832j

  日期：——

  Growing attention has been devoted in the recent years to a class of metallamacrocycles known as metallacrowns (MCs). They are structural analogues of crown ethers where the methylene bridges have been substituted by coordinative bonds formed by a transition metal ion (“ring” metal) and a nitrogen atom. The cavity of the metallacrown can accommodate an additional metal ion (“core” metal) either identical or different from the ring metal, thus forming a homo- or hetero-metallic MC. The most studied ring metal ion is certainly Cu2+ and the aminohydroxamic acids have proved to be very suitable ligands to form MCs. The behavioural analogies between Cu2+ and Ni2+ in forming complexes, along with recent literature data in the solid state, prompted us to investigate the possible MC formation between Ni2+ and both (S)-α-alaninehydroxamic acid and (S)-valinehydroxamic acid, in aqueous solution. Two metallacrowns, a 12-MC-4 and an unexpected 15-MC-5 have been detected by potentiometry and confirmed by ESI–MS results. Their structures are discussed on the basis of potentiometric, calorimetric, spectroscopic data and DFT calculations. The existence of a vacant 15-MC-5 species in solution can be put forward for the first time, making the present metal/ligand systems very interesting for their potential applications in cation recognition and separation. Finally, the crystal structure of the binary complex K[NiL2H−1]·5/3 H2O of (S)-α-alaninehydroxamic acid (LH) is also reported.

  近年来，人们越来越关注一类被称为金属冠（MC）的金属大环。它们是冠醚的结构类似物，其中的亚甲基桥被过渡金属离子（"环 "金属）和氮原子形成的配位键取代。金属冠的空腔可以容纳与环金属相同或不同的额外金属离子（"核心 "金属），从而形成同金属或杂金属 MC。研究最多的环状金属离子当然是 Cu2+，而氨基羟肟酸已被证明是非常适合形成 MC 的配体。Cu2+ 和 Ni2+ 在形成配合物时的行为相似性，以及固态下的最新文献数据，促使我们研究 Ni2+ 与 (S)-δ- 丙氨酸羟肟酸和 (S)-缬氨酸羟肟酸在水溶液中可能形成的 MC。通过电位测定法检测到了两种金属冕，一种是 12-MC-4 ，另一种是意想不到的 15-MC-5，并通过 ESIâMS 结果得到了证实。根据电位测定法、量热法、光谱数据和 DFT 计算，对它们的结构进行了讨论。首次发现溶液中存在空位 15-MC-5 物种，这使得目前的金属/配体系统在阳离子识别和分离方面的潜在应用非常有趣。最后，还报告了(S)-δ-丙氨酸羟肟酸（LH）的二元复合物 K[NiL2Hâ1]Â-5/3 H2O 的晶体结构。
• Thermodynamics of Self-Assembly of Copper(II) 15-Metallacrown-5 of Eu(III) or Gd(III) with (<i>S</i>)-α-Alaninehydroxamic Acid in Aqueous Solution
  作者：Francesco Dallavalle、Maurizio Remelli、Francesco Sansone、Dimitri Bacco、Matteo Tegoni

  DOI：10.1021/ic902146d

  日期：2010.2.15

  complexes of Cu2+ and (S)-α-alaninehydroxamic acid (α-Alaha, HL) with the lanthanide (Ln) ions Eu3+ or Gd3+ in aqueous solution are described. The binary Ln3+/α-Alaha systems were first studied by potentiometric and calorimetric in-cell titrations; the latter technique allowed us to define the most suitable speciation model. On the contrary, because the kinetics of formation of the Ln3+ 15-MC-5 complexes

  Cu 2+和（S）-α-丙氨酸异羟肟酸（α-Alaha，HL）的15-金属laclown-5（15-MC-5）配合物与镧系元素（Ln）离子Eu 3+的自组装平衡或水溶液中的Gd 3+进行了描述。首先通过电位滴定法和量热法细胞内滴定法研究了二元Ln 3+ /α-Alaha系统。后一种技术使我们能够定义最合适的物种形成模型。相反，由于Ln 3+ 15-MC-5配合物形成的动力学很慢，因此其稳定性常数由细胞外（分批）电位滴定法确定。由Eu 3+和Gd 3+形成两个15-MC-5配合物，即Ln [Cu 5 L 5 H -5 ]} 3+和Ln [Cu 5 L 5 H -5 ]（OH）} 2+，后者是前者的羟基。前者产生羟基的酸度很高（log K = 4.40-4.69）。此外，我们的电位和分光光度研究清楚地表明，氢氧根离子与中心Ln离子配位，正如固态中的几种15-MC-5所报道的那样。Ln [Cu
• FE(III)-PYRAZINE COMPLEX COMPOUNDS FOR TREATMENT AND PROPHYLAXIS OF IRON-DEFICIENCY PHENOMENA AND IRON-DEFICIENCY ANAEMIA
  申请人：VIFOR (INTERNATIONAL) AG

  公开号：US20150119374A1

  公开（公告）日：2015-04-30

  The invention relates to iron(III) complex compounds and pharmaceutical compositions comprising them for the use as medicaments, in particular for the treatment and/or prophylaxis of iron deficiency symptoms and iron deficiency anemias.

  本发明涉及铁(III)配合物化合物和包含它们的药物组合物，用作药品，特别是用于治疗和/或预防缺铁症状和缺铁性贫血。