(E) 4-amino-2-methylbut-2-en-1-ol-hydrochloride | 128121-04-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E) 4-amino-2-methylbut-2-en-1-ol-hydrochloride
• 英文别名: 2-Buten-1-ol, 4-amino-2-methyl-, hydrochloride；(E)-4-amino-2-methylbut-2-en-1-ol;hydrochloride
• CAS: 128121-04-0
• 化学式: C₅H₁₁NO*ClH
• 分子量: 137.609
• InChiKey: WAPFRSYUXWEBQV-DPZBITMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.83
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E) 4-amino-2-methylbut-2-en-1-ol-hydrochloride 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 mercury dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (+/-)-martinelline
  参考文献：
  名称：

  通过杂Diels-Alder多组分偶联反应进行生物碱马替林和马汀酸的全合成。

  摘要：

  [反应：参见正文]使用质子酸催化N-Cbz 2之间的2：1杂Diels-Alder偶联反应，精确合成了胍生物碱，（+/-）-马丁啉和（+/-）-马丁醇酸描述了吡咯啉和4-氨基苯甲酸甲酯。质子酸催化而不是路易斯酸催化对于在偶联反应中实现所需的非对映体控制意义是必需的。

  DOI：

  10.1021/ol026293d
• 作为产物：
  描述：

  (trans)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoic acid 在 盐酸 、 sodium tetrahydroborate 、 氯甲酸乙酯 、 三乙胺 作用下， 反应 5.0h， 生成 (E) 4-amino-2-methylbut-2-en-1-ol-hydrochloride
  参考文献：
  名称：

  Synthesis of the naturally occurring cytokinin 2′-deoxyzeatin riboside

  摘要：

  DOI：

  10.1016/0031-9422(90)80004-z

文献信息

• Peroxide-Shunt Substrate-Specificity for the Salmonella typhimurium O₂-Dependent tRNA Modifying Monooxygenase (MiaE)
  作者：Andra L. Corder、Bishnu P. Subedi、Siai Zhang、Amanda M. Dark、Frank W. Foss、Brad S. Pierce

  DOI：10.1021/bi4000832

  日期：2013.9.10

  Post-transcriptional modifications of tRNA are made to structurally diversify tRNA. These modifications alter noncovalent interactions within the ribosomal machinery, resulting in phenotypic changes related to cell metabolism, growth, and virulence. MiaE is a carboxylate bridged, nonheme diiron monooxygenase, which catalyzes the O-2-dependent hydroxylation of a hypermodified-tRNA nucleoside at position 37 (2-methylthio-N-6-isopentenyl-adenosine(37)-tRNA) [designated ms(2)i(6)A(37)]. In this work, recombinant MiaE was cloned from Salmonella typhimurium, purified to homogeneity, and characterized by UV-visible and dual-mode X-band EPR spectroscopy for comparison to other nonheme diiron enzymes. Additionally, three nucleoside substrate-surrogates (i(6)A, Cl(2)i(6)A, and ms(2)i(6)A) and their corresponding hydroxylated products (io(6)A, Cl(2)io(6)A, and ms(2)io(6)A) were synthesized to investigate the chemo- and stereospecificity of this enzyme. In the absence of the native electron transport chain, the peroxide-shunt was utilized to monitor the rate of substrate hydroxylation. Remarkably, regardless of the substrate (i(6)A, Cl(2)i(6)A, and ms(2)i(6)A) used in peroxide-shunt assays, hydroxylation of the terminal isopentenyl-C4-position was observed with >97% E-stereoselectivity. No other nonspecific hydroxylation products were observed in enzymatic assays. Steady-state kinetic experiments also demonstrate that the initial rate of MiaE hydroxylation is highly influenced by the substituent at the C2-position of the nucleoside base (v(0)/[E] for ms(2)i(6)A > i(6)A > Cl(2)i(6)A). Indeed, the >3-fold rate enhancement exhibited by MiaE for the hydroxylation of the free ms(2)i(6)A nucleoside relative to i(6)A is consistent with previous whole cell assays reporting the ms(2)io(6)A and io(6)A product distribution within native tRNA-substrates. This observation suggests that the nucleoside C2-substituent is a key point of interaction regulating MiaE substrate specificity:
• Total Synthesis of the Alkaloids Martinelline and Martinellic Acid via a Hetero Diels−Alder Multicomponent Coupling Reaction
  作者：David A. Powell、Robert A. Batey

  DOI：10.1021/ol026293d

  日期：2002.8.1

  [reaction: see text] A concise synthesis of the guanidine alkaloids, (+/-)-martinelline and (+/-)-martinellic acid, using a protic acid catalyzed 2:1 hetero Diels-Alder coupling reaction between N-Cbz 2-pyrroline and methyl 4-aminobenzoate, is described. Protic acid catalysis, rather than Lewis acid catalysis, was necessary to achieve the desired sense of diastereocontrol in the coupling reaction.

  [反应：参见正文]使用质子酸催化N-Cbz 2之间的2：1杂Diels-Alder偶联反应，精确合成了胍生物碱，（+/-）-马丁啉和（+/-）-马丁醇酸描述了吡咯啉和4-氨基苯甲酸甲酯。质子酸催化而不是路易斯酸催化对于在偶联反应中实现所需的非对映体控制意义是必需的。
• Synthesis of the naturally occurring cytokinin 2′-deoxyzeatin riboside
  作者：Lorenzo de Napoli、Antonio Evidente、Gennaro Piccialli、Ciro Santacroce、Rita Vellone

  DOI：10.1016/0031-9422(90)80004-z

  日期：——