ethyl (cis)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoate | 356788-86-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (cis)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoate
• 英文别名: ethyl 4-[(t-butyloxycarbonyl)amino]-2-methyl-2-butanoate；ethyl (Z)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]but-2-enoate
• CAS: 356788-86-8
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: XEGCGPIATDRIEQ-CLFYSBASSA-N

物化性质

• 沸点：
  344.1±35.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (cis)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-(4-hydroxy-3-methyl-2-butenyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Peroxide-Shunt Substrate-Specificity for the Salmonella typhimurium O₂-Dependent tRNA Modifying Monooxygenase (MiaE)

  摘要：

  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:

  DOI：

  10.1021/bi4000832
• 作为产物：
  描述：

  N-(叔丁氧基羰基)甘氨酸-N′-甲氧基-N′-甲酰胺 在 lithium aluminium tetrahydride 、 potassium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.58h， 生成 ethyl (cis)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoate
  参考文献：
  名称：

  乙烯基肽的立体选择性合成

  摘要：

  通过α-氨基醛的霍纳立体选择性烯化，将反式或顺式乙烯基插入α-氨基酸的α-碳和羧基之间。因此已经获得了许多纯的顺式和反式乙烯基α-氨基酸，并通过经典方法与氨基配偶体偶联。该方法的多功能性通过制备[反式乙烯基-Gly 3 ]亮脑啡肽来说明。

  DOI：

  10.1016/s0040-4020(01)00433-1

文献信息

• First stereoselective synthesis of potassium aeschynomate and its no-natural stereomers
  作者：Stéphanie Claudel、Tomasz Krzysztof Olszewski、Pierre Mutzenardt、Christie Aroulanda、Philippe Coutrot、Claude Grison

  DOI：10.1016/j.tet.2005.11.051

  日期：2006.2

  The synthesis of potassium aeshynomate and its non-natural stereomers was achieved using the Sharpless catalytic asymmetric dihydroxylation of (Z) or (E) vinylogous glycine as the key step. The resulting gamma-amino alpha, beta-dihydroxyester stereomer was deprotected and coupled with the caffeic acid to afford stereoselectively potassium aeshynomate or its stereomers. A detailed study of the NMR data of the different stereomers is reported that corrects the literature data. (c) 2005 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis and glycosidase inhibitory activity of 3,4-dihydroxy-pyrrolidin-2-one, 3,4-dihydroxy-piperidin-2-one and 1,2-dihydroxy-pyrrolizidin-3-one
  作者：Philippe Coutrot、Stéphanie Claudel、Claude Didierjean、Claude Grison

  DOI：10.1016/j.bmcl.2005.09.068

  日期：2006.1

  3,4-Dihydroxy-pyrrolidin-2-one, 3,4-dihydroxy-piperidin-2-one and 1, 2-dihydroxy-pyrrolizidin-3-one have been synthesized, using a simple strategy based on the asymmetric dihydroxylation of vinylogous aminoesters and subsequent mild intramolecular cyclization. All these compounds show a partial inhibition of alpha-glucosidase, but were inactive towards other glycosidases. (c) 2005 Elsevier Ltd. All rights reserved.