N-(tert-Butoxycarbonyl)glycine cyanomethyl ester | 110261-41-1

• 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)glycine cyanomethyl ester
• 英文别名: N-tert-butoxycarbonyl-glycine cyanomethyl ester；N-t-butyloxycarbonyl-glycine cyanomethyl ester；Nalpha-Boc-glycine cyanomethyl ester；cyanomethyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 110261-41-1
• 化学式: C₉H₁₄N₂O₄
• mdl: MFCD24391906
• 分子量: 214.221
• InChiKey: QPXPHOKGBKFBTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  363.6±22.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(tert-Butoxycarbonyl)glycine cyanomethyl ester 、 alkaline earth salt of/the/ methylsulfuric acid 以 N,N-二甲基甲酰胺 为溶剂， 生成 C₂₆H₃₇N₉O₁₆P₂
  参考文献：
  名称：

  Unexpected Preference of the E. coli Translation System for the Ester Bond during Incorporation of Backbone-Elongated Substrates

  摘要：

  There have been recent advances in the ribosomal synthesis of various molecules composed of nonnatural ribosomal substrates. However, the ribosome has strict limitations on substrates with elongated backbones. Here, we show an unexpected loophole in the E. coli translation system, based on a remarkable disparity in its selectivity for beta-amino/hydroxy acids. We challenged beta-hydroxypropionic acid (beta-HPA), which is less nucleophilic than beta-amino acids but free from protonation, to produce a new repertoire of ribosome-compatible but main-chain-elongated substrates. PAGE analysis and mass-coupled S-tag assays of amber suppression experiments using yeast suppressor tRNA(CUA)(Phe) confirmed the actual incorporation of beta-HPA into proteins/oligopeptides. We investigated the side-chain effects of beta-HPA and found that the side chain at position alpha and R stereochemistry of the beta-substrate is preferred and even notably enhances the efficiency of incorporation as compared to the parent substrate. These results indicate that the E. coli translation machinery can utilize main-chain-elongated substrates if the pK(a) of the substrate is appropriately chosen.

  DOI：

  10.1021/ja068033n
• 作为产物：
  描述：

  BOC-甘氨酸 、 溴乙腈 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 生成 N-(tert-Butoxycarbonyl)glycine cyanomethyl ester
  参考文献：
  名称：

  [EN] PHENAZOPYRIDINE COMPOUNDS
  [FR] COMPOSÉS DE PHÉNAZOPYRIDINE

  摘要：

  本发明涉及由式I表示的取代苯偏氨基吡啶。本发明还涉及发现，与未结合的苯偏氨基吡啶相比，式I化合物具有增加的生物利用度。

  公开号：

  WO2010071878A1

文献信息

• Incorporation of Fluorescent-Labeled Non-α-Amino Carboxylic Acids into the N-Terminus of Proteins in Response to Amber Initiation Codon
  作者：Masanori Miura、Norihito Muranaka、Ryoji Abe、Takahiro Hohsaka

  DOI：10.1246/bcsj.20090320

  日期：2010.5.15

  Incorporation of non-natural amino acid derivatives containing fluorescent groups into proteins is a useful method for protein analyses. Here, we investigated the incorporation of fluorescent-labeled non-α-amino carboxylic acids into the N-terminus of proteins in response to the UAG initiation codon. A series of TAMRA-labeled amino carboxylic acids were synthesized and attached to an amber suppressor initiator tRNA derived from Escherichia coli initiator tRNA. Fluorescent-labeled amino carboxylic acids were successfully incorporated into the N-terminus of streptavidin by adding TAMRA-acylated initiator tRNAs to an E. coli cell-free translation system, although the incorporation efficiency differed depending on the amino carboxylic acid chain length. Based on this observation, 3-aminopropionic acid derivatives labeled with BODIPY, rhodamine, and cyanine fluorophores were designed and synthesized. The fluorescent-labeled 3-aminopropionic acid derivatives developed using BODIPY and rhodamine dyes could be incorporated with good efficiency. On the other hand, 6-aminohexanoic acid was effectively incorporated when labeled with cyanine dyes. The present study demonstrates that translation initiation can accept a wide variety of non-natural substrates and provides a useful method for N-terminal-specific labeling of proteins with various fluorophores.

  将含荧光基团的非天然氨基酸衍生物掺入蛋白质中是一种有用的蛋白质分析方法。在此，我们研究了在UAG起始密码子的响应下，将荧光标记的非α-氨基酸羧酸掺入蛋白质N末端的过程。合成了一系列TAMRA标记的氨基酸羧酸，并将其连接到由大肠杆菌起始tRNA衍生的琥珀抑制起始tRNA上。通过向大肠杆菌无细胞翻译系统中添加TAMRA酰化的起始tRNA，成功地将荧光标记的氨基酸羧酸掺入链霉亲和素的N末端，尽管掺入效率因氨基酸羧酸链长而异。基于这一观察，设计并合成了使用BODIPY、罗丹明和花菁荧光染料标记的3-氨基丙酸衍生物。使用BODIPY和罗丹明染料开发的荧光标记3-氨基丙酸衍生物可以高效掺入。另一方面，当使用花菁染料标记时，6-氨基己酸可以有效掺入。本研究表明，翻译起始可以接受各种非天然底物，并提供了一种有用的方法，用于使用各种荧光团对蛋白质N末端进行特异性标记。
• Fluorinated amino acids and peptides. Synthesis of 3,3-difluoro-2-amino acids, peptides and cyclodipeptides incorporating 3,3-difluoro-2-aminobutyric acid or 3,3-difluorophenylalanine residues in their structures
  作者：A.I. Ayi、M.-L. Martos-Alcaniz、R. Condom、P.R.T. Frogier、R. Guedj

  DOI：10.1016/s0022-1139(00)81249-x

  日期：1991.11

  bonyl-DL-3,3-difluorophenylalanine which have been successfully introduced into peptide syntheses. Several fluorinated peptides have been obtained either by active ester coupling methods, mixed anhydride synthesis or with the aid of dicyclohexylcarbodiimide (DCC) in presence of 1-hydroxybenzotriazole (HOBt). The method has been applied to the preparation of seven hitherto unpublished representative

  已经开发了用于N -9-芴基甲氧基羰基-DL-2-氨基-3，3-二氟丁酸和N -9-芴基甲氧基羰基-DL-3，3-二氟苯丙氨酸的方便的合成方法，它们已经成功地引入了肽合成中。通过活性酯偶联方法，混合酸酐合成或在1-羟基苯并三唑（HOBt）存在下借助二环己基碳二亚胺（DCC）获得了几种氟化肽。该方法已用于生物学目的和结构化学研究中，迄今尚未制备的七个代表性的3-（1,1'-二氟烷基）-2,5-二氧杂哌嗪的制备。
• PHENAZOPYRIDINE COMPOUNDS
  申请人：HECHT Sidney

  公开号：US20100204185A1

  公开（公告）日：2010-08-12

  The present invention is directed to substituted phenazopyridines represented by Formula I. The present invention also relates to the discovery that compounds of Formula I have increased bioavailability as compared to unconjugated phenazopyridine.

  本发明涉及由公式I所表示的取代苯偏氨基苯的化合物。本发明还涉及发现公式I化合物相对于未结合的偏氨基苯具有增加的生物利用度。
• Phenazopyridine compounds
  申请人：Pinnacle Pharmaceuticals, Inc.

  公开号：US08288365B2

  公开（公告）日：2012-10-16

  The present invention is directed to substituted phenazopyridines represented by Formula I. The present invention also relates to the discovery that compounds of Formula I have increased bioavailability as compared to unconjugated phenazopyridine.

  本发明涉及由公式I所表示的取代苯偶氮吡啶。本发明还涉及发现公式I化合物与未结合的苯偶氮吡啶相比具有增加的生物利用度。
• Phenazopyridine Compounds
  申请人：Hecht Sidney

  公开号：US20110319367A1

  公开（公告）日：2011-12-29

  The present invention is directed to substituted phenazopyridines represented by Formula I. The present invention also relates to the discovery that compounds of Formula I have increased bioavailability as compared to unconjugated phenazopyridine.

  本发明涉及由式I表示的取代苯唑吡啶。本发明还涉及发现与非共轭苯唑啡嗪相比，式I化合物具有增加的生物利用度。