3-氨基丙烷醛 | 352-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-氨基丙烷醛
• 中文别名: 苯丁酸,g-(羟甲基)-2-甲基-
• 英文名称: 3-aminopropanal
• 英文别名: 3-aminopropionaldehyde；3-aminopropanaldehyde；β-alanin；APAL；3-amino-propionaldehyde；3-Amino-propionaldehyd
• CAS: 352-92-1
• 化学式: C₃H₇NO
• 分子量: 73.0947
• InChiKey: PCXDJQZLDDHMGX-UHFFFAOYSA-N

物化性质

• 沸点：
  45-46 °C(Press: 12 Torr)
• 密度：
  0.924±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  5
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922399090

反应信息

• 作为反应物：
  描述：

  3-氨基丙烷醛 在 Pisum sativum aminoaldehyde dehydrogenase 2 、 C₂₁H₂₇N₆O₁₅P₂⁽¹⁺⁾ 作用下， 生成 β-丙氨酸
  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
• 作为产物：
  描述：

  3-氨基-1-丙醇 在 NADH oxidase 、 alcohol dehydrogenase isoenzyme E from Equus caballus 、 nicotinamide adenine dinucleotide phosphate 作用下， 以 aq. buffer 为溶剂， 生成 3-氨基丙烷醛
  参考文献：
  名称：

  重新审视氨基醛

  摘要：

  研究氨基醇的酶促氧化以解决长期存在的产品稳定性问题。氨基醛是备受追捧的不稳定化合物，当它们立即受到保护时，可以在温和条件下生成。利用一系列醇脱氢酶 (ADH) 和氨基脲作为清除剂，可以对受保护的氨基醛进行对映选择性合成。来自氧化葡糖杆菌 (GoGDH) 的甘油脱氢酶显示出优异的对映选择性，但底物范围有限，而马肝 ADH 催化广泛的转化，但对映选择性较低。

  DOI：

  10.1002/ejoc.201701213

文献信息

• Highly dispersible and magnetically recyclable poly(1-vinyl imidazole) brush coated magnetic nanoparticles: an effective support for the immobilization of palladium nanoparticles
  作者：Ali Pourjavadi、Niloofar Safaie、Seyed Hassan Hosseini、Craig Bennett

  DOI：10.1039/c5nj02576a

  日期：——

  A heterogeneous recoverable catalyst was prepared via the complexation of palladium onto the surface of magnetic nanoparticles coated by a poly(1-vinyl imidazole) brush.

  通过在由聚(1-乙烯基咪唑)刷层包覆的磁性纳米颗粒表面上络合钯制备了一种异质可回收催化剂。
• Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them
  申请人：Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)

  公开号：US06335445B1

  公开（公告）日：2002-01-01

  A compound selected from the group consisting of a compound of the formula wherein A is selected from the group consisting of and the other substituents are defined in the specification having an inhibitory activity of NO-synthase enzymes producing nitrogen mono-oxide and/or an activity which traps the reactive oxygen species.

  从以下化合物组中选择的一种化合物，其化学式为 其中A是从以下组中选择的 其他取代基在规范中定义，具有抑制NO合酶产生一氧化氮的活性和/或捕获活性氧化物种的活性。
• Common origins of RNA, protein and lipid precursors in a cyanosulfidic protometabolism
  作者：Bhavesh H. Patel、Claudia Percivalle、Dougal J. Ritson、Colm D. Duffy、John D. Sutherland

  DOI：10.1038/nchem.2202

  日期：2015.4

  A minimal cell can be thought of as comprising informational, compartment-forming and metabolic subsystems. To imagine the abiotic assembly of such an overall system, however, places great demands on hypothetical prebiotic chemistry. The perceived differences and incompatibilities between these subsystems have led to the widely held assumption that one or other subsystem must have preceded the others. Here we experimentally investigate the validity of this assumption by examining the assembly of various biomolecular building blocks from prebiotically plausible intermediates and one-carbon feedstock molecules. We show that precursors of ribonucleotides, amino acids and lipids can all be derived by the reductive homologation of hydrogen cyanide and some of its derivatives, and thus that all the cellular subsystems could have arisen simultaneously through common chemistry. The key reaction steps are driven by ultraviolet light, use hydrogen sulfide as the reductant and can be accelerated by Cu(I)–Cu(II) photoredox cycling. A minimal cell — one that has all the minimum requirements for life — is still a complex entity comprising informational, compartment-forming and metabolic subsystems. Here it is shown that, contrary to previous assumptions, a common prebiotically plausible chemistry can give rise to building blocks for all the subsystems.

  一个最小细胞可以被认为由信息传递、分隔形成和代谢子系统组成。然而，要想象这样一个整体系统的非生物组装，对假设的产前化学提出了很高的要求。这些子系统之间感知到的差异和不兼容性导致了广泛持有的假设，即其中一个或另一个子系统必须先于其他子系统出现。在这里，我们通过检查从产前可能的中间产物和一碳供体分子组装各种生物分子构建块，来实验调查这个假设的有效性。我们表明，核糖核苷酸、氨基酸和脂质的先驱都可以通过氢氰酸及其一些衍生物的还原同系化来衍生，因此所有细胞子系统可能都通过共同的化学同时出现。关键反应步骤由紫外线驱动，使用硫化氢作为还原剂，并且可以通过Cu（I）-Cu（II）光氧化还原循环加速。一个最小细胞——一个具有生命所有最低要求的细胞——仍然是一个复杂的实体，包含信息传递、分隔形成和代谢子系统。这里表明，与之前的假设相反，一个普遍的产前可能化学可以产生所有子系统的构建块。
• Role and structural characterization of plant aldehyde dehydrogenases from family 2 and family 7
  作者：Radka Končitíková、Armelle Vigouroux、Martina Kopečná、Tomáš Andree、Jan Bartoš、Marek Šebela、Solange Moréra、David Kopečný

  DOI：10.1042/bj20150009

  日期：2015.5.15

  Aldehyde dehydrogenases (ALDHs) are responsible for oxidation of biogenic aldehyde intermediates as well as for cell detoxification of aldehydes generated during lipid peroxidation. So far, 13 ALDH families have been described in plants. In the present study, we provide a detailed biochemical characterization of plant ALDH2 and ALDH7 families by analysing maize and pea ALDH7 (ZmALDH7 and PsALDH7) and four maize cytosolic ALDH(cALDH)2 isoforms RF2C, RF2D, RF2E and RF2F [the first maize ALDH2 was discovered as a fertility restorer (RF2A)]. We report the crystal structures of ZmALDH7, RF2C and RF2F at high resolution. The ZmALDH7 structure shows that the three conserved residues Glu120, Arg300 and Thr302 in the ALDH7 family are located in the substrate-binding site and are specific to this family. Our kinetic analysis demonstrates that α-aminoadipic semialdehyde, a lysine catabolism intermediate, is the preferred substrate for plant ALDH7. In contrast, aromatic aldehydes including benzaldehyde, anisaldehyde, cinnamaldehyde, coniferaldehyde and sinapaldehyde are the best substrates for cALDH2. In line with these results, the crystal structures of RF2C and RF2F reveal that their substrate-binding sites are similar and are formed by an aromatic cluster mainly composed of phenylalanine residues and several nonpolar residues. Gene expression studies indicate that the RF2C gene, which is strongly expressed in all organs, appears essential, suggesting that the crucial role of the enzyme would certainly be linked to the cell wall formation using aldehydes from phenylpropanoid pathway as substrates. Finally, plant ALDH7 may significantly contribute to osmoprotection because it oxidizes several aminoaldehydes leading to products known as osmolytes.

  醛脱氢酶（ALDHs）负责生物醛中间产物的氧化以及脂质过氧化过程中产生的醛的细胞解毒。迄今为止，植物中已描述了 13 个 ALDH 家族。在本研究中，我们通过分析玉米和豌豆的 ALDH7（ZmALDH7 和 PsALDH7）以及四种玉米细胞质 ALDH（cALDH）2 异构体 RF2C、RF2D、RF2E 和 RF2F，对植物 ALDH2 和 ALDH7 家族进行了详细的生化鉴定[发现的第一个玉米 ALDH2 是一种生育力恢复剂（RF2A）]。我们报告了 ZmALDH7、RF2C 和 RF2F 的高分辨率晶体结构。ZmALDH7 的结构表明，ALDH7 家族中的三个保守残基 Glu120、Arg300 和 Thr302 位于底物结合位点，并且是该家族所特有的。我们的动力学分析表明，α-氨基己二酸半醛是赖氨酸分解代谢的中间产物，是植物 ALDH7 的首选底物。相比之下，芳香醛（包括苯甲醛、茴香醛、肉桂醛、针叶醛和山奈醛）是 cALDH2 的最佳底物。与这些结果相一致，RF2C 和 RF2F 的晶体结构显示，它们的底物结合位点相似，都是由一个主要由苯丙氨酸残基和几个非极性残基组成的芳香族簇构成。基因表达研究表明，RF2C 基因在所有器官中都有很强的表达，似乎是必不可少的，这表明该酶的关键作用肯定与以苯丙醛途径中的醛为底物形成细胞壁有关。最后，植物的 ALDH7 可能对渗透保护有重大贡献，因为它能氧化多种氨基醛，产生被称为渗透溶质的产物。
• An Engineered Alcohol Oxidase for the Oxidation of Primary Alcohols
  作者：Rachel S. Heath、William R. Birmingham、Matthew P. Thompson、Andreas Taglieber、Laurent Daviet、Nicholas J. Turner

  DOI：10.1002/cbic.201800556

  日期：——

  Turn up the heat: Alcohol oxidases require no cofactor or cofactor recycling system for catalysis, just O2, but their use is limited by activity and substrate scope. An alcohol oxidase with a broad scope for primary alcohol oxidations has now been evolved. Further improvements were made to enzyme stability and demonstrated by its increased thermostability and solvent tolerance.

  调高热量：醇氧化酶不需要催化的辅助因子或辅助因子循环系统，只需O 2即可，但其使用受到活性和底物范围的限制。现在已经开发出具有广泛伯醇氧化范围的醇氧化酶。酶的稳定性得到了进一步的改善，并通过增加的热稳定性和耐溶剂性得到证明。