(N-tert-butoxycarbonyl)alanine vinyl ester | 53220-28-3

• 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: (N-tert-butoxycarbonyl)alanine vinyl ester
• 英文别名: Boc-alanine vinyl ester；ethenyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 53220-28-3
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: LVVXPGFNIREWQT-ZETCQYMHSA-N

物化性质

• 沸点：
  288.8±23.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (N-tert-butoxycarbonyl)alanine vinyl ester 、 1-[(2S,3S,4S,5S)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-1,2,4-三唑-3-甲酰胺 在 吡啶 、 Bacillus subtilis subtilisin 作用下， 反应 48.0h， 以84%的产率得到
  参考文献：
  名称：

  Novel l-amino acid ester prodrugs of azacitidine: Design, enzymatic synthesis and the investigation of release behavior

  摘要：

  A facile, enzymatic synthesis protocol of L-amino acid ester prodrugs of azacitidine was developed. Firstly, transesterification of azacitidine with Boc protected vinyl aminocarboxylates was performed under the catalysis of subtilisin in anhydrous pyridine at 50 degrees C. A series of Boc-protected amino acid-azacitidine conjugates were prepared in good regioselectivity and yield. Various factors which influence the catalytic efficiency were systematically investigated. And then, the obtained azacitidine derivatives were subjected to a deprotection process to give L-amino acid ester prodrugs of azacitidine. In vitro hydrolysis of prodrugs showed that the amino acid ester prodrugs had obvious sustained release characteristic. These characteristics will have potential value for clinic application. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.03.018
• 作为产物：
  描述：

  乙酸乙烯酯 、 N-叔丁氧羰基-L-丙氨酸 在 palladium diacetate 、 potassium hydroxide 作用下， 反应 24.0h， 生成 (N-tert-butoxycarbonyl)alanine vinyl ester
  参考文献：
  名称：

  在铑纳米催化剂上利用对氢对水中的氨基酸进行超极化。

  摘要：

  NMR在化学分析，结构研究和医学诊断中提供了许多可能性。尽管已被广泛使用，但NMR光谱学的主要缺点之一是灵敏度低。超极化技术将NMR信号增强了四个数量级以上，从而允许设计新的造影剂。利用对氢的单重态产生增强信号的对氢诱导极化特别受关注，因为它可以在几秒钟内产生分子显像剂。在这里，我们提出了通过使用对氢来增强氨基酸中的羰基13 C信号的策略，如甘氨酸和丙氨酸所证明的。重要的是，超极化步骤是在水中进行的，并且获得了化学未修饰的规范氨基酸。因此，我们的方法提供了高度的生物相容性，这对于进一步应用至关重要。快速的样品超极化（几秒钟之内）可以使生物学上有用的探针（例如代谢对比剂或用于结构生物学的探针）连续产生。

  DOI：

  10.1002/chem.201902878

文献信息

• DEGRADABLE POLYCATIONS DERIVED FROM AMINO ACID VINYL ESTERS
  申请人：Wisconsin Alumini Research Foundation

  公开号：US20130184423A1

  公开（公告）日：2013-07-18

  Described herein are the synthesis and polymerization of a series of N-Boc-protected amino acid vinyl ester (BAAVE) monomers. Homopolymers and heteropolymers containing the monomers are described, particularly heteropolymers with vinyl ester monomers such as vinyl acetate. Deprotection can be used to produce hydrophilic and hydrophobic polymers that are particular useful in biological applications such as cellular delivery of biological materials.
• US8796405B2
  申请人：——

  公开号：US8796405B2

  公开（公告）日：2014-08-05
• US9688789B2
  申请人：——

  公开号：US9688789B2

  公开（公告）日：2017-06-27
• Novel l-amino acid ester prodrugs of azacitidine: Design, enzymatic synthesis and the investigation of release behavior
  作者：Fan Xu、Ming Zhang、Qi Wu、Xianfu Lin

  DOI：10.1016/j.molcatb.2014.03.018

  日期：2014.7

  A facile, enzymatic synthesis protocol of L-amino acid ester prodrugs of azacitidine was developed. Firstly, transesterification of azacitidine with Boc protected vinyl aminocarboxylates was performed under the catalysis of subtilisin in anhydrous pyridine at 50 degrees C. A series of Boc-protected amino acid-azacitidine conjugates were prepared in good regioselectivity and yield. Various factors which influence the catalytic efficiency were systematically investigated. And then, the obtained azacitidine derivatives were subjected to a deprotection process to give L-amino acid ester prodrugs of azacitidine. In vitro hydrolysis of prodrugs showed that the amino acid ester prodrugs had obvious sustained release characteristic. These characteristics will have potential value for clinic application. (C) 2014 Elsevier B.V. All rights reserved.
• Hyperpolarization of Amino Acids in Water Utilizing Parahydrogen on a Rhodium Nanocatalyst
  作者：Lukas Kaltschnee、Anil P. Jagtap、Jeffrey McCormick、Shawn Wagner、Louis‐S. Bouchard、Marcel Utz、Christian Griesinger、Stefan Glöggler

  DOI：10.1002/chem.201902878

  日期：2019.8.22

  spectroscopies main drawbacks is low sensitivity. Hyperpolarization techniques enhance NMR signals by more than four orders of magnitude allowing the design of new contrast agents. Parahydrogen induced polarization that utilizes the para-hydrogen's singlet state to create enhanced signals is of particular interest since it allows to produce molecular imaging agents within seconds. Herein, we present

  NMR在化学分析，结构研究和医学诊断中提供了许多可能性。尽管已被广泛使用，但NMR光谱学的主要缺点之一是灵敏度低。超极化技术将NMR信号增强了四个数量级以上，从而允许设计新的造影剂。利用对氢的单重态产生增强信号的对氢诱导极化特别受关注，因为它可以在几秒钟内产生分子显像剂。在这里，我们提出了通过使用对氢来增强氨基酸中的羰基13 C信号的策略，如甘氨酸和丙氨酸所证明的。重要的是，超极化步骤是在水中进行的，并且获得了化学未修饰的规范氨基酸。因此，我们的方法提供了高度的生物相容性，这对于进一步应用至关重要。快速的样品超极化（几秒钟之内）可以使生物学上有用的探针（例如代谢对比剂或用于结构生物学的探针）连续产生。