(e) 4-amino-2-methylbut-2-en-1-ol-hydrochloride | 128121-03-9

• 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
• 英文名称: (e) 4-amino-2-methylbut-2-en-1-ol-hydrochloride
• 英文别名: (E)-4-tert-butoxycarbonylamino-2-methylbut-2-en-1-ol；(E)-tert-butyl (4-hydroxy-3-methylbut-2-en-1-yl)carbamate；(E)-tert-butyl 4-hydroxy-3-methylbut-2-enylcarbamate；tert-butyl N-[(E)-4-hydroxy-3-methylbut-2-enyl]carbamate
• CAS: 128121-03-9
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: KIGCLOKIDQJFML-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (e) 4-amino-2-methylbut-2-en-1-ol-hydrochloride 在 盐酸 、 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 3.5h， 生成 6-(4-hydroxy-3-methylbut-trans-2-enylamino)-9-β-2'-deoxy-D-ribofuranosylpurine
  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
• 作为产物：
  描述：

  (trans)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoic acid 在 sodium tetrahydroborate 、 氯甲酸乙酯 、 三乙胺 作用下， 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

• Large-Scale Synthesis of (E)-4-Amino-2-Methylbut-2-en-1-ol: Key Building Block for the Synthesis of trans-Zeatin
  作者：Jianyun Pei、Jie Li、Yan Xie、Jiangsen Weng、Chengsheng Ge、Shuhua Wang

  DOI：10.14233/ajchem.2014.17644

  日期：——

  In this paper a large-scale synthesis of (E)-4-amino-2-methylbut-2-en-1-ol was disclosed and trans-zeatin could be accessed on industrial scale.

  在本文中，披露了(E)-4-氨基-2-甲基丁-2-烯-1-醇的大规模合成，trans-扎伊丁也可以在工业规模上获得。
• 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。
• 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:
• DE, NAPOLI LORENZO;EVIDENTE, ANTONIO;PICCIALLI, GENNARO;SANTACROCE, CIRO;+, PHYTOCHEMISTRY, 29,(1990) N, C. 701-703
  作者：DE, NAPOLI LORENZO、EVIDENTE, ANTONIO、PICCIALLI, GENNARO、SANTACROCE, CIRO、+

  DOI：——

  日期：——
• [EN] IMIDAZO[4,5-C]PYRIDINE DERIVATIVE COMPOUNDS AS TLR7/8 MODULATORS<br/>[FR] COMPOSÉS DÉRIVÉS D'IMIDAZO[4,5-C]PYRIDINE EN TANT QUE MODULATEURS DE TLR7/8
  申请人：[en]LEGOCHEM BIOSCIENCES, INC.

  公开号：WO2023209441A1

  公开（公告）日：2023-11-02

  Disclosed herein are immune response modulators that act on toll-like receptors and methods of use thereof.