2-hydroxyisobutyric acid anion

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxyisobutyric acid anion
• 英文别名: α-hydroxyisobutyrate；2-hydroxyisobutyrate；2-HIB；2-hydroxy-2-methylpropanoate
• 化学式: C₄H₇O₃
• 分子量: 103.098
• InChiKey: BWLBGMIXKSTLSX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲醇 、 1,2-丙二醇 在 barium hydroxide octahydrate 、 [Ir(benImi)3(CO)]BF₄ 作用下， 以 甲醇 为溶剂， 以99%的产率得到2-hydroxyisobutyric acid anion
  参考文献：
  名称：

  通过醇的催化交叉偶联模块化获得季 α-羟基乙酸酯

  摘要：

  α-羟基酸及其衍生物因其独特而广泛的功能而备受关注。在此，我们成功地建立了一个选择性和模块化的方案，通过使用三-N-杂环卡宾铱（tris-NHC-Ir，0.05 mol %）通过 1,2-二醇和伯醇的脱氢交叉偶联获得季 α-羟基乙酸酯)络合物作为催化剂和Ba(OH) 2作为碱，同时产生副产物水和氢气。提出了一种涉及醇脱氢、羟醛缩合和 1,2-烷基重排反应的合理机制，其中 1,2-烷基重排负责季碳中心的构建。

  DOI：

  10.1021/acscatal.2c05820

文献信息

• Characterizing Cation Chemistry for Anion Exchange Membranes—A Product Study of Benzylimidazolium Salt Decompositions in Base
  作者：Mark J. Pellerite、Marina M. Kaplun、Robert J. Webb

  DOI：10.1021/acs.joc.9b02493

  日期：2019.12.6

  Imidazolium functionality has played a prominent role in research on anion exchange membranes for use in alkaline electrochemical devices. Base stability and degradation of these materials has been much studied, but in many instances, product pathways have not been thoroughly delineated. We report an NMR study of base-induced decomposition products from three benzylimidazolium salts bearing varying

  咪唑鎓官能团在用于碱性电化学装置的阴离子交换膜的研究中发挥了重要作用。已经对这些材料的基本稳定性和降解进行了深入研究，但是在许多情况下，尚未全面描述产品途径。我们报告了对三个苄基咪唑鎓盐的碱基诱导的分解产物进行的NMR研究，这些盐在咪唑鎓环上具有不同程度的甲基取代。主要产物与作为分解的主要方式的水解环断裂途径一致。我们观察到了一些以前在咪唑鎓盐降解中未曾报道过的新产品，包括正式从中间体1,2-二羰基化合物或其等同物衍生而来的苯甲酸重排产品。但是，总体反应很复杂，
• Genes involved in the methyl tert-butyl ether (MTBE) metabolic pathway of Mycobacterium austroafricanum IFP 2012
  作者：Nicolas Lopes Ferreira、Diane Labbé、Frédéric Monot、Françoise Fayolle-Guichard、Charles W. Greer

  DOI：10.1099/mic.0.28585-0

  日期：2006.5.1

  Methyltert-butyl ether (MTBE) is a persistent pollutant of surface and groundwater, and the reasons for its low biodegradability are poorly documented. Using one of the rare bacterial strains able to grow in the presence of MTBE,Mycobacterium austroafricanumIFP 2012, the protein profiles of crude extracts after growth in the presence of MTBE and glucose were compared by SDS-PAGE. Ten proteins with molecular masses of 67, 64, 63, 55, 50, 27, 24, 17, 14 and 11 kDa were induced after growth in the presence of MTBE. Partial amino acid sequences of N-terminal and internal peptide fragments of the 64 kDa protein were used to design degenerate oligonucleotide primers to amplify total DNA by PCR, yielding a DNA fragment that was used as a probe for cloning. A two-step cloning procedure was performed to obtain a 10 327 bp genomic DNA fragment containing seven ORFs, including a putative regulator,mpdR, and four genes,mpdC,orf1,mpdBandorf2, in the same cluster. The MpdB protein (64 kDa) was related to a flavoprotein of the glucose–methanol–choline oxidoreductase family, and the MpdC protein (55 kDa) showed a high similarity with NAD(P) aldehyde dehydrogenases. Heterologous expression of these gene products was performed inMycobacterium smegmatismc2 155. The recombinant strain was able to degrade an intermediate of MTBE biodegradation, 2-methyl 1,2-propanediol, to hydroxyisobutyric acid. This is believed to be the first report of the cloning and characterization of a cluster of genes specifically involved in the MTBE biodegradation pathway ofM. austroafricanumIFP 2012.

  甲基叔丁基醚（MTBE）是地表水和地下水的持久性污染物，其生物降解性低的原因尚未得到充分的记录。利用一种罕见的能够在MTBE存在下生长的细菌菌株，即南非奥地利分支杆菌IFP 2012，通过SDS-PAGE比较MTBE和葡萄糖存在下生长后的粗提取物的蛋白质谱。在MTBE存在下生长后，诱导了10种分子量为67、64、63、55、50、27、24、17、14和11 kDa的蛋白质。利用64 kDa蛋白的N末端和内部肽段的部分氨基酸序列设计退化寡核苷酸引物扩增总DNA，得到一个DNA片段，用作探针进行克隆。进行了两步克隆程序，获得了一个10,327 bp的基因组DNA片段，其中包括一个假定的调节因子mpdR和四个基因mpdC、orf1、mpdB和orf2在同一簇中。MpdB蛋白（64 kDa）与葡萄糖-甲醇-胆碱氧化还原酶家族的黄酮蛋白有关，而MpdC蛋白（55 kDa）与NAD（P）醛脱氢酶具有高度相似性。在Mycobacterium smegmatis mc2 155中进行这些基因产物的异源表达。重组菌株能够将MTBE生物降解的中间体2-甲基1,2-丙二醇降解为羟基异丁酸。这被认为是首次报道了涉及M. austroafricanum IFP 2012 MTBE生物降解途径的一簇基因的克隆和表征。
• Landscape of the regulatory elements for lysine 2-hydroxyisobutyrylation pathway
  作者：He Huang、Zhouqing Luo、Shankang Qi、Jing Huang、Peng Xu、Xiuxuan Wang、Li Gao、Fangyi Li、Jian Wang、Wenhui Zhao、Wei Gu、Zhucheng Chen、Lunzhi Dai、Junbiao Dai、Yingming Zhao

  DOI：10.1038/cr.2017.149

  日期：2018.1

  Short-chain fatty acids and their corresponding acyl-CoAs sit at the crossroads of metabolic pathways and play important roles in diverse cellular processes. They are also precursors for protein post-translational lysine acylation modifications. A noteworthy example is the newly identified lysine 2-hydroxyisobutyrylation (Khib) that is derived from 2-hydroxyisobutyrate and 2-hydroxyisobutyryl-CoA. Histone Khib has been shown to be associated with active gene expression in spermatogenic cells. However, the key elements that regulate this post-translational lysine acylation pathway remain unknown. This has hindered characterization of the mechanisms by which this modification exerts its biological functions. Here we show that Esa1p in budding yeast and its homologue Tip60 in human could add Khib to substrate proteins both in vitro and in vivo. In addition, we have identified HDAC2 and HDAC3 as the major enzymes to remove Khib. Moreover, we report the first global profiling of Khib proteome in mammalian cells, identifying 6 548 Khib sites on 1 725 substrate proteins. Our study has thus discovered both the “writers” and “erasers” for histone Khib marks, and major Khib protein substrates. These results not only illustrate the landscape of this new lysine acylation pathway, but also open new avenues for studying diverse functions of cellular metabolites associated with this pathway.

  短链脂肪酸及其相应的酰基-CoA位于代谢途径的交叉点，在各种细胞过程中发挥着重要作用。它们也是蛋白质翻译后赖氨酸酰化修饰的前体。一个值得注意的例子是新近发现的赖氨酸2-羟基异丁酰化（Khib），它来自2-羟基异丁酸和2-羟基异丁酰-CoA。组蛋白Khib已被证明与精原细胞中的活跃基因表达有关。然而，调节这种翻译后赖氨酸酰化途径的关键因素仍然未知。这阻碍了对这种修饰发挥其生物学功能的机制的描述。在这里，我们展示了在体外和体内，芽孢酵母中的Esa1p和人类中的同源物Tip60都可以将Khib添加到底物蛋白上。此外，我们已经确定了HDAC2和HDAC3作为去除Khib的主要酶。此外，我们报告了哺乳动物细胞中Khib蛋白组的首次全球分析，在1725个底物蛋白上鉴定出6548个Khib位点。因此，我们的研究发现了组蛋白Khib标记的“书写者”和“擦除者”，以及主要的Khib蛋白底物。这些结果不仅说明了这种新的赖氨酸酰化途径的景观，而且为研究与此途径
• Modular Access to Quaternary α-Hydroxyl Acetates by Catalytic Cross-Coupling of Alcohols
  作者：Guangkuo Zeng、Jiajie Wu、Lingyun Shen、Qingshu Zheng、Zhe-Ning Chen、Xin Xu、Tao Tu

  DOI：10.1021/acscatal.2c05820

  日期：2023.2.3

  tris-N-heterocyclic carbene iridium (tris-NHC-Ir, 0.05 mol %) complexes as catalysts and Ba(OH)2 as the base, along with the generation of byproducts water and hydrogen gas. A plausible mechanism involving dehydrogenation of alcohols, aldol-condensation, and 1,2-alkyl rearrangement reactions was proposed, in which 1,2-alkyl rearrangement was responsible for the construction of the quaternary carbon center.

  α-羟基酸及其衍生物因其独特而广泛的功能而备受关注。在此，我们成功地建立了一个选择性和模块化的方案，通过使用三-N-杂环卡宾铱（tris-NHC-Ir，0.05 mol %）通过 1,2-二醇和伯醇的脱氢交叉偶联获得季 α-羟基乙酸酯)络合物作为催化剂和Ba(OH) 2作为碱，同时产生副产物水和氢气。提出了一种涉及醇脱氢、羟醛缩合和 1,2-烷基重排反应的合理机制，其中 1,2-烷基重排负责季碳中心的构建。