1,4-Butanediammonium

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,4-Butanediammonium
• 英文别名: 4-azaniumylbutylazanium
• 化学式: C4H14N2+2
• 分子量: 90.17
• InChiKey: KIDHWZJUCRJVML-UHFFFAOYSA-P

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  6
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.3
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-Butanediammonium 生成 铵 、 Sym-homospermidinium(3+)
  参考文献：
  名称：

  细菌高嘧啶合酶-一种多胺代谢的必需酶的综合结构特征。

  摘要：

  高度保守的细菌高嘧啶合酶（HSS）是许多变形杆菌多胺代谢的关键酶，包括诸如肺炎军团菌和铜绿假单胞菌等致病菌株。NAD（H）作为修复基团的独特用法是细菌HSS，真核HSS和脱氧hysupsine合酶（DHS）的共同特征。细菌酶的结构在活性中心不具有赖氨酸残基，因此不会形成DHS所观察到的酶-底物席夫碱中间体。与DHS相比，活性位点不是由两个亚基的界面形成，而是位于细菌HSS的一个亚基内。Blastochloris viridis HSS（BvHSS）的晶体结构揭示了两个不同的底物结合位点，其中之一对腐胺具有高度特异性。BvHSS在由保守氨基酸形成的活性位点的直接附近具有一个侧袋，并具有潜在的底物识别，引导和传感机制。提议的催化BvHSS的反应步骤强调了通过保守的Trp残基作为高能过渡态的关键稳定剂的阳离子-π相互作用。

  DOI：

  10.1038/srep19501
• 作为产物：
  描述：

  N-(4-aminobutyl)-3-aminopropanal 生成 丙烯醛 、 1,4-Butanediammonium
  参考文献：
  名称：

  The biological functions of polyamine oxidation products by amine oxidases: Perspectives of clinical applications

  摘要：

  The polyamines spermine, spermidine and putrescine are ubiquitous cell components. If they accumulate excessively within the cells, due either to very high extracellular concentrations or to deregulation of the systems which control polyamine homeostasis, they can induce toxic effects. These molecules are substrates of a class of enzymes that includes monoamine oxidases, diamine oxidases, polyamine oxidases and copper containing amine oxidases. Polyamine concentrations are high in growing tissues such as tumors. Amine oxidases are important because they contribute to regulate levels of mono- and polyamines. These enzymes catalyze the oxidative deamination of biogenic amines and polyamines to generate the reaction products H2O2 and aldehyde(s) that are able to induce cell death in several cultured human tumor cell lines. H2O2 generated by the oxidation reaction is able to cross the inner membrane of mitochondria and directly interact with endogenous molecules and structures, inducing an intense oxidative stress. Since amine oxidases are involved in many crucial physiopathological processes, investigations on their involvement in human diseases offer great opportunities to enter novel classes of therapeutic agents.

  DOI：

  10.1007/s00726-004-0114-4

文献信息

• Plant C-N Hydrolases and the Identification of a Plant N-Carbamoylputrescine Amidohydrolase Involved in Polyamine Biosynthesis
  作者：Markus Piotrowski、Tim Janowitz、Helmut Kneifel

  DOI：10.1074/jbc.m205699200

  日期：2003.1

  expressed in Escherichia coli as a His(6)-tagged protein and purified to apparent homogeneity by Ni(2+)-chelate affinity chromatography. The purified enzyme showed N-carbamoylputrescine amidohydrolase activity, an enzyme involved in the biosynthesis of polyamines in plants and bacteria. N-carbamoylputrescine amidohydrolase activity was confirmed by identification of two of the three occurring products

  来自拟南芥（NLP1）的腈水解酶样蛋白在大肠杆菌中以His（6）标记蛋白表达，并通过Ni（2 +）-螯合亲和层析纯化至表观同质性。纯化的酶显示出N-氨基甲酰氨基酪胺酰胺水解酶活性，该酶参与植物和细菌中多胺的生物合成。通过鉴定三种发生的产物中的两种，即腐胺和氨，证实了N-氨基甲酰氨基鸟氨酸的酰胺水解酶活性。相反，当施用包括腈，胺和酰胺的各种化合物以及其他N-氨基甲酰基化合物时，未检测到酶活性，表明该酶对N-氨基甲酰基酪氨酰胺的特异性。像同源的β-丙氨酸合酶一样，NLP1对其底物表现出正的协同作用。如蓝色天然聚丙烯酰胺凝胶电泳所示，该天然酶的分子量为279 kDa，指示八个单体的复合物。在所有研究的器官中均发现了NLP1基因的表达，但在渗透胁迫下并未被诱导表达，众所周知，渗透胁迫可诱导腐胺的生物合成。这是首次克隆和表达植物N-氨基甲酰氨苄丝氨酸酰胺水解酶的报道，并且是首次在体外显示重组蛋白的N
• Acetylpolyamine amidohydrolase from Mycoplana ramosa: gene cloning and characterization of the metal-substituted enzyme
  作者：K Sakurada、T Ohta、K Fujishiro、M Hasegawa、K Aisaka

  DOI：10.1128/jb.178.19.5781-5786.1996

  日期：1996.10

  We have cloned a gene (aphA) encoding acetylpolyamine amidohydrolase from Mycoplana ramosa ATCC 49678, (previously named Mycoplana bullata). A genomic library of M. ramosa was screened with an oligonucleotide probe designed from a N-terminal amino acid sequence of the enzyme purified from M. ramosa. Nucleotide sequence analysis revealed an open reading frame of 1,023 bp which encodes a polypeptide with a molecular mass of 36,337 Da. This is the first report of the structure of acetylpolyamine amidohydrolase. The aphA gene was subcloned under the control of the trc promoter and was expressed in Escherichia coli MM294. The recombinant enzyme was purified, and the enzymatic properties were characterized. Substrate specificities, Km values, and Vmax values were identical to those of the native enzyme purified from M. ramosa. In the analysis of the metal-substituted enzymes, we found that the acid limb of pH rate profiles shifts from 7.2 for the original zinc enzyme to 6.6 for the cobalt enzyme. This change suggests that the zinc atom is essential for the catalytic activity of the enzyme similarly to the zinc atom in carboxypeptidase A.

  我们已经克隆了一个来自Mycoplana ramosa ATCC 49678（之前被称为Mycoplana bullata）的编码乙酰多胺酰胺水解酶的基因（aphA）。使用从M. ramosa中纯化的酶N末端氨基酸序列设计的寡核苷酸探针筛选了M. ramosa的基因组文库。核苷酸序列分析揭示了一个长1023个碱基的开放阅读框架，编码一个分子量为36,337 Da的多肽。这是有关乙酰多胺酰胺水解酶结构的首次报道。aphA基因在trc启动子的控制下亚克隆，并在大肠杆菌MM294中表达。重组酶被纯化，并对其酶学性质进行了表征。底物特异性，Km值和Vmax值与从M. ramosa中纯化的天然酶相同。在金属替代酶的分析中，我们发现pH速率曲线的酸性端从原始锌酶的7.2转移到钴酶的6.6。这种变化表明锌原子对于酶的催化活性至关重要，类似于羧肽酶A中的锌原子。
• Expression of Atropa belladonna Putrescine N-Methyltransferase Gene in Root Pericycle
  作者：K.-i. Suzuki、Y. Yamada、T. Hashimoto

  DOI：10.1093/oxfordjournals.pcp.a029540

  日期：1999.1.1

  The cDNAs encoding putrescine N-methyltransferase (PMT), which catalyzes the S-adenosylmethionine-dependent N-methylation of putrescine at the first committed step in the biosynthetic pathways of tropane alkaloids, were isolated from Atropa belladonna and Hyoscyamus niger. These PMTs, however, lacked the N-terminal tandem repeat arrays previously found in Nicotiana PMTs. AbPMT1 RNA was much more abundant in the root of A. belladonna than was AbPMT2 RNA. The 5′-flanking region of the AbPMT1 gene was fused to the β-glucuronidase (GUS) reporter gene and transferred to A. belladonna. Histochemical analysis showed that GUS is expressed specifically in root pericycle cells and that the 0.3-kb 5′-upstream region was sufficient for pericycle-specific expression. Treatment of A. belladonna roots with methyl jasmonate did not up-regulate the expression of GUS or endogenous AbPMT genes. The regulation of tropane alkaloid biosynthesis is discussed and compared with that of nicotine biosynthesis.

  从颠茄（Atropa belladonna）和黑毛莨（Hyoscyamus niger）中分离出了编码腐胺 N-甲基转移酶（PMT）的 cDNAs。然而，这些 PMTs 缺乏以前在烟草 PMTs 中发现的 N 端串联重复阵列。颠茄根中的 AbPMT1 RNA 要比 AbPMT2 RNA 丰富得多。AbPMT1 基因的 5′ 侧翼区域与 β-葡糖醛酸酶（GUS）报告基因融合，并转入颠茄。组织化学分析表明，GUS 在根周皮细胞中特异性表达，0.3 kb 的 5′-上游区域足以实现根周皮特异性表达。用茉莉酸甲酯处理颠茄根不会上调 GUS 或内源 AbPMT 基因的表达。本文讨论了甜菜碱生物合成的调控，并与尼古丁生物合成的调控进行了比较。
• Homospermidine synthase, the first pathway-specific enzyme of pyrrolizidine alkaloid biosynthesis, evolved from deoxyhypusine synthase
  作者：Dietrich Ober、Thomas Hartmann

  DOI：10.1073/pnas.96.26.14777

  日期：1999.12.21

  Pyrrolizidine alkaloids are preformed plant defense compounds with sporadic phylogenetic distribution. They are thought to have evolved in response to the selective pressure of herbivory. The first pathway-specific intermediate of these alkaloids is the rare polyamine homospermidine, which is synthesized by homospermidine synthase (HSS). The HSS gene from Senecio vernalis was cloned and shown to be

  吡咯烷核生物碱是预先形成的具有零星系统发生分布的植物防御化合物。人们认为它们是根据食草动物的选择压力进化而来的。这些生物碱的第一个途径特异性中间体是稀有的多胺高嘧啶，它是由高嘧啶合酶（HSS）合成的。克隆了来自千里光的HSS基因，并显示其衍生自脱氧hypusine合酶（DHS）基因，该基因在所有真核生物和古细菌中高度保守。DHS催化了翻译起始因子5A（eIF5A）激活的第一步，这对于真核细胞增殖至关重要，它是HIV-1 Rev调节蛋白的辅助因子。
• Isolation and Characterization of a Mutant of <i>Escherichia coli</i> Blocked in the Synthesis of Putrescine
  作者：I. N. Hirshfield、H. J. Rosenfeld、Z. Leifer、W. K. Maas

  DOI：10.1128/jb.101.3.725-730.1970

  日期：1970.3

  A mutant of Escherichia coli is described which is defective in the conversion of arginine to putrescine. The activity of the enzyme agmatine ureohydrolase is greatly reduced, whereas the activity of the other two enzymes of the pathway, the constitutive arginine decarboxylase and the inducible arginine decarboxylase, are within the normal range. The growth behavior of the mutant reflects the enzymatic block. It grows well in the absence of arginine, but only poorly in the presence of arginine. Under the former conditions, putrescine can be formed from ornithine as well as arginine, whereas under the latter conditions, because of feedback control, it can be formed only from arginine.

  描述了一种突变的大肠杆菌，其在将精氨酸转化为腐胺方面存在缺陷。鸟氨酸尿素水解酶的酶活性大大降低，而通路中的另外两种酶，即组成性精氨酸脱羧酶和诱导性精氨酸脱羧酶的活性在正常范围内。突变体的生长行为反映了酶的阻塞。在没有精氨酸的情况下，它可以良好地生长，但在精氨酸存在的情况下，生长仅很差。在前一种情况下，腐胺可以从鸟氨酸和精氨酸中形成，而在后一种情况下，由于反馈控制，它只能从精氨酸中形成。