章鱼碱 | 14358-35-1

• 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
• 中文名称: 章鱼碱
• 英文名称: N^α-(2-carboxy-ethyl)-L-arginine
• 英文别名: N^α-(2-Carboxy-aethyl)-L-arginin；L-2-(2-Carboxy-aethylamino)-5-guanidino-valeriansaeure；β-Octopin；N2-(2-carboxyethyl)-(S)-arginine；(2S)-5-{[amino(iminio)methyl]amino}-2-[(2-carboxylatoethyl)azaniumyl]pentanoate；(2S)-2-(2-carboxylatoethylazaniumyl)-5-(diaminomethylideneazaniumyl)pentanoate
• CAS: 14358-35-1
• 化学式: C₉H₁₈N₄O₄
• mdl: MFCD00070083
• 分子量: 246.266
• InChiKey: OHWCFZJEIHZWMN-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  章鱼碱 在 recombinant ORF₃ protein 、 magnesium 、 5’-三磷酸腺苷 作用下， 生成 (2S)-5-guanidino-2-(2'-oxazetidin-1'-yl)pentanoic acid
  参考文献：
  名称：

  β-Lactam synthetase: implications for β-lactamase evolution

  摘要：

  合成酶在克拉维酸生物合成过程中催化单环β-内酰胺环的形成。

  DOI：

  10.1039/a806713i
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 生成 章鱼碱
  参考文献：
  名称：

  两个新的精氨酸衍生物从链霉菌的突变体。

  摘要：

  N 2-（2-羧乙基）精氨酸和N 2-（2-羧乙基）-3-羟基精氨酸的两个新型精氨酸衍生物是由棒状链霉菌dclH 65的一个突变体产生的，该突变体在棒酸的生物合成中被阻断，并且其结构的化合物表明它们可能参与了棒酸的生物合成。

  DOI：

  10.1039/c39930001211

文献信息

• DEVICE AND METHOD FOR SOLUBILIZING, SEPARATING, REMOVING AND REACTING CARBOXYLIC ACIDS IN OILS, FATS, AQUEOUS OR ORGANIC SOLUTIONS BY MEANS OF MICRO-OR NANOEMULSIFICATION
  申请人：Dietz Ulrich

  公开号：US20130090488A1

  公开（公告）日：2013-04-11

  The present invention is directed to solubilizing compounds, a device and a method for solubilizing and removing carboxylic acids and especially fatty acids from oils, fats, aqueous emulsion, aqueous media and organic solutions. Devices utilizing the inventive method shall be used for separating carboxylic acids from oils, fats, aqueous emulsion, lipophilic media or organic solutions, respectively by preparing an aqueous micro- or nanoemulsion of the carboxylic acids especially the fatty acids and the solubilizing compound which contains at least one amidino and/or gianidino group. Solubilization effects of solubilizing compounds combined with the inventive use of separation methods for carboxylic acids can be used to treat persons in need of removal of fatty acids or analyze carboxylic acids from blood or process other solutions in food, pharmacy, chemistry, bio fuel industry or other industrial processings.

  本发明涉及溶解化合物、用于从油、脂肪、水乳液、水介质和有机溶液中溶解和去除羧酸，特别是脂肪酸的装置和方法。采用本发明方法的装置将用于通过制备羧酸特别是脂肪酸和含有至少一种氨基甲酰基和/或肼基团的溶解化合物的水微观或纳米乳液，分离油、脂肪、水乳液、亲脂性介质或有机溶液中的羧酸。溶解化合物的溶解效果与本发明所述的羧酸分离方法相结合，可用于治疗需要去除脂肪酸或从血液中分析羧酸或处理食品、药品、化学、生物燃料工业或其他工业加工过程中的其他溶液的人员。
• The catalytic cycle of β-lactam synthetase observed by x-ray crystallographic snapshots
  作者：Matthew T. Miller、Brian O. Bachmann、Craig A. Townsend、Amy C. Rosenzweig

  DOI：10.1073/pnas.232361199

  日期：2002.11.12

  The catalytic cycle of the ATP/Mg ²⁺ -dependent enzyme β-lactam synthetase (β-LS) from Streptomyces clavuligerus has been observed through a series of x-ray crystallographic snapshots. Chemistry is initiated by the ordered binding of ATP/Mg ²⁺ and N ² -(carboxyethyl)- l -arginine (CEA) to the apoenzyme. The apo and ATP/Mg ²⁺ structures described here, along with the previously described CEA⋅α,β-methyleneadenosine 5′-triphosphate (CEA⋅AMP-CPP)/Mg ²⁺ structure, illuminate changes in active site geometry that favor adenylation. In addition, an acyladenylate intermediate has been trapped. The substrate analog N ² -(carboxymethyl)- l -arginine (CMA) was adenylated by ATP in the crystal and represents a close structural analog of the previously proposed CEA-adenylate intermediate. Finally, the structure of the ternary product complex deoxyguanidinoproclavaminic acid (DGPC)⋅AMP/PP _i /Mg ²⁺ has been determined. The CMA-AMP/PP _i /Mg ²⁺ and DGPC⋅AMP/PP _i /Mg ²⁺ structures reveal interactions in the active site that facilitate β-lactam formation. All of the ATP-bound structures differ from the previously described CEA⋅AMP-CPP/Mg ²⁺ structure in that two Mg ²⁺ ions are found in the active sites. These Mg ²⁺ ions play critical roles in both the adenylation and β-lactamization reactions.

  ATP/Mg2+依赖性酶β-内酰胺合成酶（β-LS）来自于Streptomyces clavuligerus，其催化循环已通过一系列x射线晶体学快照观察到。化学反应由有序结合ATP/Mg2+和N2-(羧乙基)-L-精氨酸（CEA）到裸酶开始。此处描述的裸酶和ATP/Mg2+结构以及先前描述的CEA⋅α，β-甲基腺苷5'-三磷酸（CEA⋅AMP-CPP）/Mg2+结构，阐明了有利于腺苷酸化的活性位点几何变化。此外，已捕获到酰腺苷酸中间体。底物类似物N2-(羧甲基)-L-精氨酸（CMA）在晶体中被ATP腺苷化，代表了先前提出的CEA-腺苷酸中间体的近似结构类似物。最后，已确定三元产物复合物脱氧鸟氨酸丙卡拉维酸（DGPC）⋅AMP/PPi/Mg2+的结构。CMA-AMP/PPi/Mg2+和DGPC⋅AMP/PPi/Mg2+结构揭示了促进β-内酰胺形成的活性位点相互作用。所有ATP结合的结构与先前描述的CEA⋅AMP-CPP/Mg2+结构不同，因为在活性位点中发现了两个Mg2+离子。这些Mg2+离子在腺苷酸化和β-内酰胺化反应中发挥关键作用。
• Spectroscopic Studies of Substrate Interactions with Clavaminate Synthase 2, a Multifunctional α-KG-Dependent Non-Heme Iron Enzyme:  Correlation with Mechanisms and Reactivities
  作者：Jing Zhou、Wendy L. Kelly、Brian O. Bachmann、Michele Gunsior、Craig A. Townsend、Edward I. Solomon

  DOI：10.1021/ja004025+

  日期：2001.8.1

  five-coordinate only when both substrate and alpha-KG are bound, the latter still in a bidentate mode. Absorption, CD, MCD, and VTVH MCD studies of the interaction of CS2 with DGPC, PC, and DPC provide significant molecular level insight into the structure/function correlations of this multifunctional enzyme. There are varying amounts of six-coordinate ferrous species in the substrate complexes, which correlate

  使用单个亚铁活性位点，克拉瓦酸合酶 2 (CS2) 激活 O(2) 并催化脱氧胍基内酰胺酸 (DGPC) 的羟基化、内酰胺原酸 (PC) 的氧化闭环和二氢克拉维胺酸（和底物）的去饱和类似物，脱氧原丙氨酸（DPC）），每个都与共底物α-酮戊二酸（α-KG）的氧化脱羧相结合。CS2 还可以在底物存在和不存在的情况下催化 α-KG 的非偶联脱羧，从而导致酶失活。静止的 CS2/Fe(II) 有一个六配位的 Fe(II) 位点，α-KG 以双齿模式与铁结合。只有当底物和 alpha-KG 都结合时，活性位点才变成五坐标，后者仍处于双齿模式。吸收，CD，MCD，CS2 与 DGPC、PC 和 DPC 相互作用的 VTVH MCD 研究为这种多功能酶的结构/功能相关性提供了重要的分子水平洞察力。底物复合物中存在不同数量的六配位亚铁物质，这与非偶联反应相关。所有三种底物/α-KG 复合物都存在具有相似几
• New reactions in clavulanic acid biosynthesis
  作者：Craig A Townsend

  DOI：10.1016/s1367-5931(02)00392-7

  日期：2002.10

  Clavulanic acid is only a modestly effective antibiotic against bacterial infections in humans, but a potent inhibitor/inactivator of beta-lactamase enzymes that confer bacterial resistance. The biosynthetic pathway to clavulanic acid is considerably more complex than that to the structurally related penicillins and cephalosporins and has revealed several interesting reactions.

  棒酸只是对人类细菌感染的中度有效抗生素，但是有效的β-内酰胺酶抑制剂/灭活剂，可赋予细菌抗药性。棒酸的生物合成途径比与结构相关的青霉素和头孢菌素的生物合成途径复杂得多，并且已经揭示了一些有趣的反应。
• Device and method for solubilizing, separating, removing and reacting carboxylic acids in aqueous or organic solutions by means of micro- or nanoemulsification
  申请人：Dietz, Ulrich

  公开号：EP2399885A1

  公开（公告）日：2011-12-28

  The invention is related to the emulsification effects achiveable by arginine and arginine analogues on carboxylic acids in aqueous and organic media and the use of these effects to solubilize, separate and remove carboxylic acids as well as increasing physical or chemical interactions and reactions. Furthermore, the invention is directed to the nanoemulsifying properties of arginine and arginine analogues on carboxlic acids and poorly soluble molecules. Solubilization effects of arginine and arginine analogues combined with the inventive use of separation methods for carboxylic acids can be used to treat persons in need of removal of fatty acids or analyze carboxylic acids from blood or process other solutions in food, pharmacy, chemistry or other industrial processings. The inventive effects of arginine and arginine analogues enable the use of methods for nano-filtration of carboxylic acids. Moreover, the use of arginine and arginine anlogues as well as carboxylic acids used to functionalize the interface of micro- and nanofluidic separation media including hydro- or organogels by means of surface functionalization, adsorption or incorporation enables the use of electrophoretic and nanofiltration techniques to be applied on carboxylic acids.

  本发明涉及精氨酸和精氨酸类似物在水性和有机介质中对羧酸的乳化作用，以及利用这些作用来增溶、分离和去除羧酸以及增加物理或化学相互作用和反应。此外，本发明还涉及精氨酸和精氨酸类似物对羧酸和难溶分子的纳米乳化特性。精氨酸和精氨酸类似物的增溶作用与羧酸分离方法的创造性使用相结合，可用于治疗需要去除脂肪酸的人，或分析血液中的羧酸，或处理食品、制药、化学或其他工业加工中的其他溶液。精氨酸和精氨酸类似物的创造性作用使得纳米过滤羧酸的方法得以使用。此外，使用精氨酸和精氨酸类似物以及羧酸，通过表面官能化、吸附或结合的方式，使包括水凝胶或有机凝胶在内的微流体和纳米流体分离介质的界面功能化，可将电泳和纳滤技术应用于羧酸。