γ-胍丁酸 | 463-00-3

• 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: γ-胍丁酸
• 中文别名: 4-胍基丁酸
• 英文名称: 4-guanidinobutyric acid
• 英文别名: 4-guanidinobutanoic acid；4-guanidinobutanoate；γ-guanidinobutyric acid；guanidinobutyric acid；4‑guanidinobutyric acid；γ-GBA；HL 6450；4-Guanidinobutyrate；4-(diaminomethylideneazaniumyl)butanoate
• CAS: 463-00-3
• 化学式: C₅H₁₁N₃O₂
• mdl: MFCD00037314
• 分子量: 145.161
• InChiKey: TUHVEAJXIMEOSA-UHFFFAOYSA-N

物化性质

• 熔点：
  280-282 °C
• 沸点：
  322.2±44.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于水基（轻微），水（轻微）
• 物理描述：
  Solid
• 碰撞截面：
  129.7 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
• 稳定性/保质期：

  按规格使用和贮存，不会发生分解，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  2925290090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封保存，放置于通风、干燥的地方，避免与其它氧化物接触。

制备方法与用途

生物活性：4-单脒基丁酸（4-Guanidinobutanoate, γ-单脒基丁酸, γ-单脒基丁酸）是一种低浓度的正常代谢物。

靶点：

人类内源性代谢物

反应信息

• 作为反应物：
  描述：

  γ-胍丁酸 生成 4-氨基丁酸
  参考文献：
  名称：

  Thomas, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1913, vol. 88, p. 471

  摘要：

  DOI：
• 作为产物：
  描述：

  4-胍基丁醛 在 Pisum sativum aminoaldehyde dehydrogenase 2 、 nicotinamide adenine dinucleotide 作用下， 生成 γ-胍丁酸
  参考文献：
  名称：

  Structural and Functional Characterization of Plant Aminoaldehyde Dehydrogenase from Pisum sativum with a Broad Specificity for Natural and Synthetic Aminoaldehydes

  摘要：

  Aminoaldehyde dehydrogenases (AMADHs, EC 1.2.1.19) belong to the large aldehyde dehydrogenase (ALDH) superfamily, namely, the ALDH9 family. They oxidize polyamine-derived omega-aminoaldehydes to the corresponding omega-amino acids. Here, we report the first X-ray structures of plant AMADHs: two isoenzymes, PsAMADH1 and PsAMADH2, from Pisum sativum in complex with beta-nicotinamide adenine dinucleotide (NAD(+)) at 2.4 and 2.15 angstrom resolution, respectively. Both recombinant, proteins are dimeric and, similarly to other ALDHs, each monomer is composed of an oligomerization domain, a coenzyme binding domain and a catalytic domain. Each subunit binds NAD(+) as a coenzyme, contains a solvent-accessible C-terminal peroxisomal targeting signal (type 1) and a cation bound in the cavity close to the NAD(+) binding site. While the NAD(+) binding mode is classical for PsAMADH2, that for PsAMADH1 is unusual among ALDHs. A glycerol molecule occupies the substrate binding site and mimics a bound substrate. Structural analysis and substrate specificity study of both isoenzymes in combination with data published previously on other ALDH9 family members show that the established categorization of such enzymes into distinct groups based on substrate specificity is no more appropriate, because many of them seem capable of oxidizing a large spectrum of aminoaldehyde substrates. PsAMADH1 and PsAMADH2 can oxidize N,N,N-trimethyl-4-aminobutyraldehyde into gamma-butyrobetaine, which is the carnitine precursor in animal cells. This activity highly suggests that in addition to their contribution to the formation of compatible osmolytes such as glycine betaine, beta-alanine betaine and gamma-aminobutyric acid, AMADHs might participate in carnitine biosynthesis in plants. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jmb.2009.12.015

文献信息

• [DE] PI3-KINASEN<br/>[EN] PI3 KINASES<br/>[FR] PI3-KINASES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2006040279A1

  公开（公告）日：2006-04-20

  Es werden neue Verbindungen der Formel (1) bereitgestellt, die aufgrund ihrer pharmazeutischen Wirksamkeit als PI3-Kinase Modulator zur Anwendung auf therapeutischem Gebiet zur Behandlung von entzündlichen oder allergischen Erkrankungen gelangen können. Beispielhaft seien hier entzündliche und allergische Atemwegserkrankungen, entzündliche Erkrankungen des Magen-Darm-Traktes und des Bewegungsapparates, entzündliche und allergische Hauterkrankungen, entzündliche Augenerkrankungen, Erkrankungen der Nasenschleimhaut, entzündliche oder allergische Krankheitszustände, bei denen Autoimmun-Reaktionen beteiligt sind oder Nierenentzündungen genannt.

  提供公式（1）的新颖化合物，由于其药理活性可作为PI3激酶调节剂应用于治疗领域，用于治疗炎性疾病或过敏性疾病。例如，这里可以列举的包括炎性和过敏性呼吸道疾病、炎性疾病、胃肠道的运动系统、炎性和过敏性皮肤病、炎性疾病、鼻粘膜疾病、炎症或过敏性疾病，其中涉及自身免疫反应或肾盂肾炎。
• Structure of mildiomycin D.
  作者：Shigeki TASHIRO、Norio SUGITA、Takashi IWASA、Hidekazu SAWADA

  DOI：10.1271/bbb1961.48.881

  日期：——

  A new nucleoside antibiotic, mildiomycin D, was isolated from the culture broth of Streptoverticillium rimofaciens B-98891as a minor component. Themolecular formula of the antibiotic purified by silica gel and ion exchange resin columnchromatographies was determined to be C19H30N8O8• (2H2O) from its physicochemical data. The ultraviolet and infrared spectra were very similar to those ofmildiomycin, a major component. On the basis of 1H and 13C-NMRspectra and acidic hydrolysates of the compound, the chemical structure of the antibiotic was determined as a deoxy compound at the C8, position in mildiomycin. Mildiomycin D showed weak activities against Gram-positive and negative bacteria, phytopathogenic fungi and some yeasts, and its activity against Rhodotorula rubura was about 40% that of mildiomycin.

  一种新的核苷类抗生素Mildiomycin D从Streptoverticillium rimofaciens B-98891的发酵液中被分离出来，作为次要成分。通过硅胶和离子交换树脂柱层析纯化的抗生素分子式根据其物理化学数据被确定为C19H30N8O8•(2H2O)。紫外和红外光谱与主要成分mildiomycin非常相似。根据1H和13C-NMR光谱及该化合物的酸性水解产物，确定了该抗生素的化学结构为mildiomycin中C8位上的去氧化合物。Mildiomycin D对革兰氏阳性及阴性细菌、植物病原真菌和某些酵母菌显示出微弱的活性，其对红酵母的活性约为mildiomycin的40%。
• Snapshots of the Catalytic Cycle of an O₂, Pyridoxal Phosphate-Dependent Hydroxylase
  作者：Jason B. Hedges、Eugene Kuatsjah、Yi-Ling Du、Lindsay D. Eltis、Katherine S. Ryan

  DOI：10.1021/acschembio.8b00039

  日期：2018.4.20

  Enzymes that catalyze hydroxylation of unactivated carbons normally contain heme and nonheme iron cofactors. By contrast, how a pyridoxal phosphate (PLP)-dependent enzyme could catalyze such a hydroxylation was unknown. Here, we investigate RohP, a PLP-dependent enzyme that converts l-arginine to (S)-4-hydroxy-2-ketoarginine. We determine that the RohP reaction consumes oxygen with stoichiometric release

  催化未活化碳羟基化的酶通常包含血红素和非血红素铁辅助因子。相比之下，磷酸吡ido醛（PLP）依赖性酶如何催化这种羟基化是未知的。在这里，我们研究RohP，一种PLP依赖性酶，可将1-精氨酸转化为（S）-4-羟基-2-酮精氨酸。我们确定RohP反应消耗化学计量的H 2 O 2释放氧气。为了理解这种不寻常的化学反应，我们获得了约1.5Å的分辨率结构，可沿催化循环捕获中间体。我们的数据表明RohP进行四电子氧化和立体定向烯烃水合以生成（S）配置的产品。连同我们对O 2，依赖PLP的l-精氨酸氧化酶的早期研究一起，我们的工作表明存在一条共同的途径导致l-精氨酸的氧化和羟基化产物。
• Deposition of new thia-containing Schiff-base iron (III) complexes onto carbon nanotube-modified glassy carbon electrodes as a biosensor for electrooxidation and determination of amino acids
  作者：Lotfali Saghatforoush、Mohammad Hasanzadeh、Nasrin Shadjou、Balal Khalilzadeh

  DOI：10.1016/j.electacta.2010.10.031

  日期：2011.1

  Multiwall carbon nanotubes (MWCNTs) were used as an immobilization matrix to incorporate an Fe (III)–Schiff base complex as an electron-transfer mediator onto a glassy carbon electrode surface. First, the preheated glassy carbon was subjected to abrasive immobilization of MWCNTs by gently rubbing the electrode surface on filter paper supporting the carbon nanotubes. Second, the electrode surface was

  多壁碳纳米管（MWCNT）用作固定基质，将Fe（III）–Schiff碱配合物作为电子转移介体掺入玻璃碳电极表面。首先，通过在支撑碳纳米管的滤纸上轻轻摩擦电极表面，对预热的玻璃碳进行MWCNT的磨料固定。其次，通过浇铸100μLFe（III）络合物溶液（ACN中为0.01 M）来修饰电极表面。水溶液中修饰电极的循环伏安图显示了一对定义明确，稳定且几乎可逆的具有表面受限特性的还原氧化还原系统。MWCNTs和Fe（III）-Schiff碱配合物独特的电子和电催化性能的组合产生了显着的协同增效作用。通过循环伏安法表征了修饰电极在pH 1–9的水溶液中的电化学行为和稳定性。表观电子传递速率常数（K s）和传递系数（a）通过循环伏安法测定，分别约为7 s -1和0.55。修饰的电极在酸性溶液中具有非同寻常的正电位，对氨基酸的氧化表现出出色的催化活性。它们还显示出在宽pH范围，快速响应时间，高灵敏度，
• A Common Origin for Guanidinobutanoate Starter Units in Antifungal Natural Products
  作者：Hui Hong、Taicia Fill、Peter F. Leadlay

  DOI：10.1002/anie.201308136

  日期：2013.12.2

  Keeping it basic: Arginine provides the exotic 4‐guanidinobutanoate starter unit for two different types of zwitterionic polyketide (an example for one type is shown in the picture) produced by the same Streptomyces bacterium. The three‐step precursor pathway is initiated by a remarkable decarboxylating monooxygenase with high specificity for arginine.

  保持基础：精氨酸为同一种链霉菌属细菌生产的两种不同类型的两性离子聚酮化合物提供异乎寻常的4-胍基丁酸酯入门单元。三步前体途径是由对精氨酸具有高度特异性的脱羧单加氧酶引发的。