2-氨基-2-丙烯酸 | 1948-56-7

• 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: 2-氨基-2-丙烯酸
• 英文名称: dehydroalanine
• 英文别名: 2-aminoacrylic acid；2-azaniumylprop-2-enoate
• CAS: 1948-56-7
• 化学式: C₃H₅NO₂
• 分子量: 87.0782
• InChiKey: UQBOJOOOTLPNST-UHFFFAOYSA-N

物化性质

• 沸点：
  251.2±23.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  2-氨基-2-丙烯酸 生成 2-Iminopropionsaeure
  参考文献：
  名称：

  Crystal Structure of Serine Dehydratase from Rat Liver^,

  摘要：

  SDH (L-serine dehydratase, EC 4.3.1.17) catalyzes the pyridoxal 5'-phosphate (PLP)-dependent dehydration of L-serine to yield pyruvate and ammonia. Liver SDH plays an important role in gluconeogenesis. Formation of pyruvate by SDH is a two-step reaction in which the hydroxyl group of serine is cleaved to produce aminoacrylate, and then the aminoacrylate is deaminated by nonenzymatic hydrolysis to produce pyruvate. The crystal structure of rat liver apo-SDH was determined by single isomorphous replacement at 2.8 A resolution. The holo-SDH crystallized with O-methylserine (OMS) was also determined at 2.6 A resolution by molecular replacement. SDH is composed of two domains, and each domain has a typical alphabeta-open structure. The active site is located in the cleft between the two domains. The holo-SDH contained PLP-OMS aldimine in the active site, indicating that OMS can form the Schiff base linkage with PLP, but the subsequent dehydration did not occur. Apo-SDH forms a dimer by inserting the small domain into the catalytic cleft of the partner subunit so that the active site is closed. Holo-SDH also forms a dimer by making contacts at the back of the clefts so that the dimerization does not close the catalytic cleft. The phosphate group of PLP is surrounded by a characteristic G-rich sequence ((168)GGGGL(172)) and forms hydrogen bonds with the amide groups of those amino acid residues, suggesting that the phosphate group can be protonated. N(1) of PLP participates in a hydrogen bond with Cys303, and similar hydrogen bonds with N(1) participating are seen in other beta-elimination enzymes. These hydrogen bonding schemes indicate that N(1) is not protonated, and thus, the pyridine ring cannot take a quinone-like structure. These characteristics of the bound PLP suggest that SDH catalysis is not facilitated by forming the resonance-stabilized structure of the PLP-Ser aldimine as seen in aminotransferases. A possible catalytic mechanism involves the phosphate group, surrounded by the characteristic sequence, acting as a general acid to donate a proton to the leaving hydroxyl group of serine.

  DOI：

  10.1021/bi035324p
• 作为产物：
  描述：

  N^ε-3-(3-methyl-3H-diazirine-3-yl)-propaminocarbonyl-γ-seleno-L-lysine 在 双氧水 作用下， 生成 3-(3-methyldiazirin-3-yl)propyl N-(2-hydroxyselanylethyl)carbamate 、 2-氨基-2-丙烯酸
  参考文献：
  名称：

  Genetically Encoded Cleavable Protein Photo-Cross-Linker

  摘要：

  We have developed a genetically encoded, selenium-based cleavable photo-cross-linker that allows for the separation of bait and prey proteins after protein photo-cross-linking. We have further demonstrated the efficient capture of the in situ generated selenenic acid on the cleaved prey proteins. Our strategy involves tagging the selenenic acid with an alkyne-containing dimethoxyaniline molecule and subsequently labeling with an azide-bearing fluorophore or biotin probe. This cleavage-and-capture after protein photo-cross-linking strategy allows for the efficient capture of prey proteins that are readily accessible by two-dimensional gel-based proteomics and mass spectrometry analysis.

  DOI：

  10.1021/ja504371w
• 作为试剂：
  描述：

  苯丁酮 在 三氟甲磺酸三甲基硅酯 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 2,6-二甲基-4-苯基-1,4-二氢吡啶-3,5-二羧酸二乙酯 、 对甲苯磺酸 、 2-氨基-2-丙烯酸 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Ketals对α-第三级醚的光催化还原形成。

  摘要：

  报道了构造不对称α-叔二烷基醚的一般光催化还原策略。通过合并路易斯酸介导的缩酮活化和可见光光催化还原，发现原位生成的α-烷氧基与多种烯烃伙伴参与了加成反应。一系列芳香族和脂肪族酮的缩酮证明了良好的反应效率。还描述了对缩醛底物的扩展，证明了该方法在复杂醚合成中的整体合成效用。

  DOI：

  10.1021/acs.orglett.9b02273

文献信息

• Chinazolincarbonsäuren. VII. Mitteilung. Ein einfacher Zugang zu (4-Oxo-3,4-dihydrochinazolin-3-yl)-alkansäuren, (4-Oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)-alkansäuren und deren Estern
  作者：Manfred Süsse、Siegfried Johne

  DOI：10.1002/hlca.19850680410

  日期：1985.6.26

  Quinazoline Carboxylic Acids. An Easy Route to (4-Oxo-3,4-dihydroquinazolin-3-yl)-alkanoic Acids, (4-Oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)-alkanoic Acids and their Esters

  喹唑啉羧酸。轻松合成（4-Oxo-3,4-dihydroquinazolin-3-yl）-链烷酸，（4-Oxo-3,4-dihydro-1,2,3-3-苯并三嗪-3-基）-链烷酸和他们的酯
• Purification and Characterization of Cystine Lyase a from Broccoli Inflorescence
  作者：Koji Ukai、Jiro Sekiya

  DOI：10.1271/bbb.61.1890

  日期：1997.1

  One of the three isoforms of an enzyme degrading L-cystine was purified to homogeneity from broccoli (Brassica oleracea var. italica) inflorescences, with use of a sensitive assay based on derivatization of a reaction product with monobromobimane. The reaction product with a thiol group was found to be thiocysteine from results of liquid chromatography-mass spectrometry and high-resolution mass spectrometry. Pyruvate was also a reaction product, formed in equimolar amounts. The purified enzyme catalyzed β-elimination of L-cystine to yield thiocysteine, pyruvate and possibly ammonia, so it was cystine lyase a. L-Cystine but not D-cystine was a substrate of the enzyme. S-Methyl L-cysteine sulfoxide and S-ethyl L-cysteine sulfoxide were substrates but were less suitable than L-cystine. L- and D-cysteine and also cystathionine were not substrates. The purified enzyme (Mr 186,000) was composed of four identical subunits (Mr 45,000) and was pyridoxal 5′-phosphate-dependent.

  从西兰花（Brassica oleracea var. italica）的花序中，通过对反应产物与溴代二溴萘的衍生化作用，利用一种灵敏的检测方法，将三种同工酶之一的一种降解L-胱氨酸的酶纯化至均一性。通过液相色谱-质谱联用和高分辨率质谱分析结果发现，具有巯基的反应产物为硫代半胱氨酸。丙酮酸也是反应产物，其生成量与L-胱氨酸等摩尔。纯化的酶催化L-胱氨酸的β-消去反应，产生硫代半胱氨酸、丙酮酸，可能还有氨，因此它是胱氨酸裂解酶a。L-胱氨酸而非D-胱氨酸是该酶的底物。S-甲基-L-半胱氨酸亚砜和S-乙基-L-半胱氨酸亚砜是底物，但不如L-胱氨酸合适。L-和D-半胱氨酸以及胱硫醚不是底物。纯化的酶（分子量186,000）由四个相同的亚基（分子量45,000）组成，并依赖于吡哆醛5'-磷酸。
• N-Pyrazinoyl Substituted Amino Acids as Potential Antimycobacterial Agents—the Synthesis and Biological Evaluation of Enantiomers
  作者：Martin Juhás、Lucie Kučerová、Ondřej Horáček、Ondřej Janďourek、Vladimír Kubíček、Klára Konečná、Radim Kučera、Pavel Bárta、Jiří Janoušek、Pavla Paterová、Jiří Kuneš、Martin Doležal、Jan Zitko

  DOI：10.3390/molecules25071518

  日期：——

  tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC < 1.95 µg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.

  结核病是由结核分枝杆菌（Mtb）引起的传染病，每年导致数百万人死亡。在本文中，我们介绍了新型潜在抗分枝杆菌化合物的合成和生物学评价，该化合物含有一线抗结核药物吡嗪酰胺（PZA）的片段，以及选定氨基酸的甲酯或乙酯。对多种（分枝）细菌菌株（包括 Mtb H37Ra、耻垢分枝杆菌、金黄色分枝杆菌、金黄色葡萄球菌、铜绿假单胞菌）和真菌菌株（包括白色念珠菌和黄曲霉）的抗菌活性进行了评估。重点放在对映体活性的比较上。合成的化合物均未表现出明显的抗真菌活性，且抗菌活性也较低，最佳最低抑菌浓度（MIC）值为31.25 µM。然而，有几种化合物对 Mtb 具有很高的活性。总体而言，含有 L-氨基酸的衍生物具有更高的活性。同样，该活性似乎与亲脂性更强的化合物有关。最活跃的衍生物含有苯基甘氨酸部分（PC-d/l-Pgl-Me，MIC < 1.95 µg/mL）。所有活性化合物均具有低细胞毒性和对 Mtb 的良好
• Biosynthetic Gene Cluster of Linaridin Peptides Contains Epimerase Gene
  作者：Wanlu Xiao、Yasuharu Satoh、Yasushi Ogasawara、Tohru Dairi

  DOI：10.1002/cbic.202100705

  日期：2022.6.20

  Heterologous expression experiments of three linaridin biosynthetic gene clusters revealed that the presence of multiple D-amino acids is a common feature of linaridin natural products, and unveiled the involvement of novel peptide epimerases conserved among linaridin clusters. By gene-deletion experiments, we also show that peptide epimerization occurs in the early stage of biosynthesis.

  三个linaridin生物合成基因簇的异源表达实验表明，存在多个D-氨基酸是linaridin天然产物的共同特征，并揭示了linaridin簇中保守的新型肽差向异构酶的参与。通过基因缺失实验，我们还表明肽差向异构发生在生物合成的早期阶段。
• MICROFLUIDIC PROTEIN CRYSTALLOGRAPHY
  申请人：Hansen Carl L.

  公开号：US20110306522A1

  公开（公告）日：2011-12-15

  The use of microfluidic structures enables high throughput screening of protein crystallization. In one embodiment, an integrated combinatoric mixing chip allows for precise metering of reagents to rapidly create a large number of potential crystallization conditions, with possible crystal formations observed on chip. In an alternative embodiment, the microfluidic structures may be utilized to explore phase space conditions of a particular protein crystallizing agent combination, thereby identifying promising conditions and allowing for subsequent focused attempts to obtain crystal growth.

  微流控结构的使用使得蛋白质结晶的高通量筛选成为可能。在一种实施方式中，集成的组合混合芯片允许精确计量试剂，以快速创建大量可能的结晶条件，并在芯片上观察到可能的晶体形成。在另一种实施方式中，微流控结构可以用于探索特定蛋白质结晶剂组合的相空间条件，从而确定有前途的条件，并允许随后集中尝试获得晶体生长。