2-hydroxy-ethanesulfonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-hydroxy-ethanesulfonate
• 英文别名: 2-hydroxyethanesulfonate；isethionate；2-hydroxyethanesulphonate
• 化学式: C₂H₅O₄S
• 分子量: 125.125
• InChiKey: SUMDYPCJJOFFON-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-ethanesulfonate 、 1,2-乙二磺酸 以 水 为溶剂， 生成 2-羟乙基磺酸 、 硫酸
  参考文献：
  名称：

  Process for the production of taurine from ethanol

  摘要：

  本发明揭示了一种从乙烯酸和乙醇制备牛磺酸的方法，通过乙醇衍生的乙烯酸，通过乙烯酸的氨解和乙烯酸制备的关键中间体——异丙酸钠和乙烯基磺酸钠的氨解。

  公开号：

  US20150210633A1
• 作为产物：
  描述：

  乙烷磺酸钠盐 在 sodium hexachloroplatinate 硫酸 、 氧气 、 copper dichloride 作用下， 160.0 ℃ 、2.07 MPa 条件下， 反应 4.0h， 生成 羟基乙酸 、 2-hydroxy-ethanesulfonate 、 Carboxy-methanesulfonic acid anion 、 2,2-Dihydroxyethanesulfonate
  参考文献：
  名称：

  Shilov催化化学：氯化铂催化双氧氧化末端甲基。

  摘要：

  DOI：

  10.1021/ja001926+
• 作为试剂：
  描述：

  α,α-dimethyl-4-(α,α,β,β-tetrafluorophenethyl)benzylamine 、 2-羟乙基磺酸 在 2-hydroxy-ethanesulfonate 、 乙醚 、 水 作用下， 以 异丙醇 为溶剂， 生成 alpha,alpha-Dimethyl-4-(alpha,alpha,beta,beta-tetrafluorophenethyl)-benzylamine isethionate
  参考文献：
  名称：

  Arylperfluoroalkanes

  摘要：

  新的芳基烷基胺衍生物，特别是2-(2-苯基-1,1,2,2-四氟乙基)苯甲胺及其N-烷基和N,N-二烷基衍生物，是通过2-溴苯甲腈与苯基镁氯反应制备2'-溴-2-苯乙酮；用硒酸氧化该苯乙酮制备2-溴苯并咪唑；通过用四氟化硫处理苯并咪唑化合物制备相应的2-溴-α,α,α',α'-四氟联苯；随后将2-溴联苯化合物与金属氰化物反应制备相应的2-(2-苯基-1,1,2,2-四氟乙基)苯甲腈。然后，该腈化合物用氢化铝锂还原制备相应的苯甲胺，如果需要，可以将其转化为N-烷基和/或N,N-二烷基2-(2-苯基-1,1,2,2-四氟乙基)苯甲胺。或者，腈或前体溴联苯可以通过格氏反应转化为相应的α-烷基或α,α-二烷基苯甲胺，如果需要，可以将其转化为相应的N-烷基和/或N,N-二烷基取代的苯甲胺化合物。苯基四氟乙基苯甲胺及其N-烷基和N,N-二烷基衍生物作为抗心律失常剂具有活性。

  公开号：

  US04071570A1

文献信息

• Glucan Compositions
  申请人：Baschong Werner

  公开号：US20090156563A1

  公开（公告）日：2009-06-18

  A cosmetic or pharmaceutical composition is provided comprising: a) 0.001 to less than 0.2% by weight, based on the weight of the total composition, of a scleroglucan having a mean molecular weight of 1×10 6 to 12×10 6 ; b) a cosmetically or pharmaceutically acceptable carrier; and, optionally, c) lactic acid, a lactate and/or pentanediol. The composition shows advantageous effects, such as moisturization of skin or mucosa, and has an antiaging and revitalizing effect on the skin. When combined with a certain bactericide as explained in claim 1 , compositions containing native polysaccharides of the glucan class in general, especially of the scleroglucan as of component a), are well suitable to reduce the number of bacteria in mucosal or oral environments and minimise adhesion, while retaining a pleasant feeling on the mucosa or gingiva. Plaque thus can be efficiently prevented or removed.

  提供一种化妆品或药物组合物，其中包括：a）占总组合物重量的0.001至少于0.2％，具有平均分子量为1×106至12×106的硬木糖聚糖；b）化妆品或药用可接受载体；以及可选的c）乳酸，乳酸盐和/或戊二醇。该组合物具有优越的效果，例如保湿皮肤或黏膜，并对皮肤具有抗衰老和活化作用。当与特定的杀菌剂结合使用时，通常含有葡聚糖类的天然多糖，特别是硬木糖聚糖作为a）组分的组合物非常适合减少黏膜或口腔环境中的细菌数量并最小化附着，同时在黏膜或牙龈上保持愉悦感。因此，可以有效地预防或去除牙菌斑。
• Isethionate formation from taurine in Chromohalobacter salexigens: purification of sulfoacetaldehyde reductase
  作者：Zdeněk Krejčík、Klaus Hollemeyer、Theo H. M. Smits、Alasdair M. Cook

  DOI：10.1099/mic.0.036699-0

  日期：2010.5.1

  Bacterial generation of isethionate (2-hydroxyethanesulfonate) from taurine (2-aminoethanesulfonate) by anaerobic gut bacteria was established in 1980. That phenomenon in pure culture was recognized as a pathway of assimilation of taurine-nitrogen. Based on the latter work, we predicted from genome-sequence data that the marine gammaproteobacterium Chromohalobacter salexigens DSM 3043 would exhibit this trait. Quantitative conversion of taurine to isethionate, identified by mass spectrometry, was confirmed, and the taurine-nitrogen was recovered as cell material. An eight-gene cluster was predicted to encode the inducible vectorial, scalar and regulatory enzymes involved, some of which were known from other taurine pathways. The genes (Csal_0153–Csal_0156) encoding a putative ATP-binding-cassette (ABC) transporter for taurine (TauAB₁B₂C) were shown to be inducibly transcribed by reverse transcription (RT-) PCR. An inducible taurine : 2-oxoglutarate aminotransferase [EC 2.6.1.55] was found (Csal_0158); the reaction yielded glutamate and sulfoacetaldehyde. The sulfoacetaldehyde was reduced to isethionate by NADPH-dependent sulfoacetaldehyde reductase (IsfD), a member of the short-chain alcohol dehydrogenase superfamily. The 27 kDa protein (SDS-PAGE) was identified by peptide-mass fingerprinting as the gene product of Csal_0161. The putative exporter of isethionate (IsfE) is encoded by Csal_0160; isfE was inducibly transcribed (RT-PCR). The presumed transcriptional regulator, TauR (Csal_0157), may autoregulate its own expression, typical of GntR-type regulators. Similar gene clusters were found in several marine and terrestrial gammaproteobacteria, which, in the gut canal, could be the source of not only mammalian, but also arachnid and cephalopod isethionate.

  1980年，通过厌氧肠道细菌从牛磺酸（2-氨基乙磺酸）生成异丝氨酸（2-羟基乙磺酸）的现象在纯培养中被确认为牛磺酸氮同化的途径。基于这项工作，我们从基因组序列数据中预测，海洋伽马变形菌Chromohalobacter salexigens DSM 3043将表现出这种特性。通过质谱法确认了牛磺酸向异丝氨酸的定量转化，并将牛磺酸氮作为细胞物质回收。预测有一个由八个基因组成的簇编码诱导的矢量、标量和调节酶，其中一些酶从其他牛磺酸途径已知。通过反转录（RT-PCR）显示编码牛磺酸（TauAB1B2C）的一个假定的ATP结合盒（ABC）转运体的基因（Csal_0153-Csal_0156）被诱导转录。发现了一个诱导的牛磺酸：2-酮戊二酸氨基转移酶[EC 2.6.1.55]（Csal_0158）；该反应产生谷氨酸和磺乙醛。磺乙醛通过NADPH依赖的磺乙醛还原酶（IsfD）还原为异丝氨酸，该酶是短链醇脱氢酶超家族的成员。通过肽质量指纹鉴定，27 kDa蛋白质（SDS-PAGE）被识别为Csal_0161的基因产物。异丝氨酸的假定转运蛋白（IsfE）由Csal_0160编码；isfE被诱导转录（RT-PCR）。假定的转录调节因子TauR（Csal_0157）可能会自调节其自身表达，这是GntR类型调节因子的典型特征。在几种海洋和陆地伽马变形菌中发现了类似的基因簇，在肠道中可能是哺乳动物、蜘蛛和头足类异丝氨酸的来源。
• A glycyl radical enzyme enables hydrogen sulfide production by the human intestinal bacterium <i>Bilophila wadsworthia</i>
  作者：Spencer C. Peck、Karin Denger、Anna Burrichter、Stephania M. Irwin、Emily P. Balskus、David Schleheck

  DOI：10.1073/pnas.1815661116

  日期：2019.2.19

  This paper describes a pathway for anaerobic bacterial metabolism of taurine (2-aminoethanesulfonate), an abundant substrate in the human intestinal microbiota, by the intestinal bacterium and opportunistic pathogen, Bilophila wadsworthia . This metabolism converts taurine to the toxic metabolite hydrogen sulfide (H ₂ S), an activity associated with inflammatory bowel disease and colorectal cancer. A critical enzyme in this pathway is isethionate sulfite-lyase, a member of the glycyl radical enzyme family. This enzyme catalyzes a novel, radical-based C-S bond-cleavage reaction to convert isethionate (2-hydroxyethanesulfonate) to sulfite and acetaldehyde. This discovery improves our understanding of H ₂ S production in the human body and may also offer new approaches for controlling intestinal H ₂ S production and B. wadsworthia infections.

  本文描述了肠道细菌和机会性病原体Bilophila wadsworthia对人类肠道微生物中丰富的底物牛磺酸（2-氨基乙磺酸）的厌氧代谢途径。这种代谢将牛磺酸转化为有毒代谢物氢硫化物（H₂S），与炎症性肠病和结直肠癌有关。该途径中的关键酶是异丝氨酸亚硫酸盐裂解酶，属于甘氨酰基辐射酶家族。该酶催化一种新颖的基于自由基的C-S键断裂反应，将异丝氨酸（2-羟基乙磺酸）转化为亚硫酸盐和乙醛。这一发现提高了我们对人体内H₂S产生的理解，也可能为控制肠道H₂S产生和B. wadsworthia感染提供新的方法。

• Radical-mediated C-S bond cleavage in C2 sulfonate degradation by anaerobic bacteria
  作者：Meining Xing、Yifeng Wei、Yan Zhou、Jun Zhang、Lianyun Lin、Yiling Hu、Gaoqun Hua、Ankanahalli N. Nanjaraj Urs、Dazhi Liu、Feifei Wang、Cuixia Guo、Yang Tong、Mengya Li、Yanhong Liu、Ee Lui Ang、Huimin Zhao、Zhiguang Yuchi、Yan Zhang

  DOI：10.1038/s41467-019-09618-8

  日期：——

  catalyzes the radical-mediated C-S bond cleavage of isethionate to form sulfite and acetaldehyde. We demonstrate its involvement in pathways that enables C2 sulfonates to be used as terminal electron acceptors for anaerobic respiration in sulfate- and sulfite-reducing bacteria. Furthermore, it plays a key role in converting bile salt-derived taurine into H2S in the disease-associated gut bacterium

  有机磺酸盐的细菌降解在硫的再循环中起着重要作用，并且已被广泛研究。然而，尽管厌氧细菌特别是肠道细菌中的这种过程可能会产生有毒的H 2 S，对人类健康产生潜在的重大影响，但鲜为人知。在这里，我们描述了一种催化自由基的氧敏感性酶的结构和生化特性。乙硫酸酯介导的CS键裂解形成亚硫酸盐和乙醛。我们证明了其参与使C2磺酸盐用作硫酸盐和亚硫酸盐还原细菌厌氧呼吸的末端电子受体的途径。此外，它在将胆盐衍生的牛磺酸转化为H 2中起关键作用。■在与疾病相关的肠道细菌Bilophila wadsworthia。这些厌氧途径中的酶和转运蛋白扩展了我们对微生物硫代谢的理解，并有助于破译与肠道中硫化合物转化有关的复杂微生物途径网。
• Characterization of a Two-component Alkanesulfonate Monooxygenase from Escherichia coli
  作者：Eric Eichhorn、Jan R. van der Ploeg、Thomas Leisinger

  DOI：10.1074/jbc.274.38.26639

  日期：1999.9

  The Escherichia coli ssuEADCB gene cluster is required for the utilization of alkanesulfonates as sulfur sources, and is expressed under conditions of sulfate or cysteine starvation. The SsuD and SsuE proteins were overexpressed and characterized. SsuE was purified to homogeneity as an N-terminal histidine-tagged fusion protein. Native SsuE was a homodimeric enzyme of ill, 58,400, which catalyzed an NAD(P)H-dependent reduction of FMN, but it was also able to reduce FAD or riboflavin, The SsuD protein was purified to >98% purity using cation exchange, anion exchange, and hydrophobic interaction chromatography. The pure enzyme catalyzed the conversion of pentanesulfonic acid to sulfite and pentaldehyde and was able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers. SsuD catalysis was absolutely dependent on FMNH2 and oxygen, and was maximal for SsuE/SsuD molar ratios of 2.1 to 4.2 in 10 mM Tris-HCl, pH 9.1. Native SsuD was a homotetrameric enzyme of M-r 181,000. These results demonstrate that SsuD is a broad range FMNH2-dependent monooxygenase catalyzing the oxygenolytic conversion of alkanesulfonates to sulfite and the corresponding aldehydes, SsuE is the FMN reducing enzyme providing SsuD with FMNH2.

表征谱图