NVOC-Gly-OH | 135997-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: NVOC-Gly-OH
• 英文别名: N-{[(4,5-Dimethoxy-2-nitrophenyl)methoxy]carbonyl}glycine；2-[(4,5-dimethoxy-2-nitrophenyl)methoxycarbonylamino]acetic acid
• CAS: 135997-56-7
• 化学式: C₁₂H₁₄N₂O₈
• 分子量: 314.252
• InChiKey: LBHGGOLEHFQCFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  三氟乙酸五氟苯酯 、 NVOC-Gly-OH 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以73%的产率得到perfluorophenyl (((4,5-dimethoxy-2-nitrobenzyl)oxy)carbonyl)glycinate
  参考文献：
  名称：

  Synthesis of Pentafluorophenyl Esters of Nitroveratryloxycarbonyl-Protected Amino Acids

  摘要：

  为了在玻璃芯片上高效合成肽，通过使用五氟苯基三氟乙酸盐合成了20种硝基藜芦氧羰基（NVOC）保护的氨基酸的五氟苯基（Pfp）酯。简单的纯化步骤提供了中等至高产率。每个氨基酸在玻璃表面上的第一次加载时间为30-60分钟。NVOC基团的紫外光裂解在10分钟内完成。

  DOI：

  10.1055/s-0029-1218369
• 作为产物：
  描述：

  (4,5-Dimethoxy-2-nitro-benzyloxycarbonylamino)-acetic acid allyl ester 在 RhCl(PPh₃)3 作用下， 以 乙醇 、 水 为溶剂， 生成 NVOC-Gly-OH
  参考文献：
  名称：

  固相合成中的顺序可光裂解的保护基。

  摘要：

  [反应：见正文]使用光不稳定的连接基和保护基团开发了顺序的固相肽合成方法。利用叔丁基酮衍生的连接基（对305 nm的辐射敏感）和硝基过碳酰氧羰基（NVOC）基团（对360 nm敏感）之间的色序不稳定性来制备亮氨酸-脑啡肽，总产率为55％。通过避免使用常见的脱保护试剂（例如三氟乙酸或哌啶），该新策略允许在基本中性的介质中制备肽。

  DOI：

  10.1021/ol027454g

文献信息

• Sortase‐Mediated Multi‐Fragment Assemblies by Ligation Site Switching
  作者：Jan Bierlmeier、Miguel Álvaro‐Benito、Maren Scheffler、Kristina Sturm、Luisa Rehkopf、Christian Freund、Dirk Schwarzer

  DOI：10.1002/anie.202109032

  日期：2022.1.26

  Sortase-mediated ligation (SML) of multiple peptide fragments is enabled by ligation site switching. An active sorting motif installed by default into the ligation product is switched from an active to an inactive state while a latent nucleophile in the ligation product is activated for SML. Repetitive cycles of SML and ligation site switching allow the assembly of multiple fragments with wild type sortase.

  通过连接位点转换实现多个肽片段的分选酶介导的连接 (SML)。默认情况下安装到连接产物中的活性分选基序从活性状态切换为非活性状态，同时连接产物中的潜在亲核试剂被激活用于 SML。 SML 和连接位点切换的重复循环允许使用野生型分选酶组装多个片段。
• Automated Maskless Photolithography System for Peptide Microarray Synthesis on a Chip
  作者：Dong-Sik Shin、Kook-Nyung Lee、Byung-Wook Yoo、Jaehi Kim、Mira Kim、Yong-Kweon Kim、Yoon-Sik Lee

  DOI：10.1021/cc100009g

  日期：2010.7.12

  Maskless photolithographic peptide synthesis was performed on a glass chip using an automated peptide array synthesizer system. The peptide array synthesizer was built in a closed box, which contained optical and fluidic systems. The conditions for peptide synthesis were fully controlled by a computer program. For the peptide synthesis on a glass chip, 20 NVOC-protected amino acids were synthesized. The coupling efficiencies of two model peptide sequences were examined on ACA/APTS and PEG/CHI/GPTS chips. PEG/CHI/GPIS chip gave higher average stepwise yields of GIYWHHY (94%) and YIYGSFK (98%) than those of ACA/APTS chip. To quantify peptide-protein binding affinity, HPQ- or HPM-containing pentapeptides were synthesized on a PEG/CHI/GPTS chip and the binding event of Cy3 labeled-streptavidin was quantified. The peptide sequence of IQHPQ showed highest binding affinity with Cy3 labeled-streptavidin. The results demonstrated that the photolithographic peptide array synthesis method efficiently quantified the binding activities of protein-peptide interactions and it can be used for additional biological assay applications.
• Synthesis of Pentafluorophenyl Esters of Nitroveratryloxycarbonyl-Protected Amino Acids
  作者：Yoon-Sik Lee、Dong-Sik Shin

  DOI：10.1055/s-0029-1218369

  日期：2009.12

  For efficient peptide synthesis on a glass chip, 20 kinds of pentafluorophenyl (Pfp) esters of nitroveratryloxycarbonyl (NVOC)-protected amino acids were synthesized by using Pfp tri­fluoroacetate. Simple purification step gave moderate to high yield. The first loading time of each amino acid on glass surface was 30-60 min. The UV cleavage of the NVOC group was completed within 10 minutes.

  为了在玻璃芯片上高效合成肽，通过使用五氟苯基三氟乙酸盐合成了20种硝基藜芦氧羰基（NVOC）保护的氨基酸的五氟苯基（Pfp）酯。简单的纯化步骤提供了中等至高产率。每个氨基酸在玻璃表面上的第一次加载时间为30-60分钟。NVOC基团的紫外光裂解在10分钟内完成。
• Sequentially Photocleavable Protecting Groups in Solid-Phase Synthesis
  作者：Martin Kessler、Ralf Glatthar、Bernd Giese、Christian G. Bochet

  DOI：10.1021/ol027454g

  日期：2003.4.1

  [reaction: see text] A sequential solid-phase peptide synthesis was developed using both photolabile linker and protecting groups. The chromatic sequential lability between a tert-butyl ketone-derived linker (sensitive to irradiation at 305 nm) and a nitroveratryloxycarbonyl (NVOC) group (sensitive at 360 nm) was exploited to prepare Leu-Enkephalin in a 55% overall yield. This new strategy allows the

  [反应：见正文]使用光不稳定的连接基和保护基团开发了顺序的固相肽合成方法。利用叔丁基酮衍生的连接基（对305 nm的辐射敏感）和硝基过碳酰氧羰基（NVOC）基团（对360 nm敏感）之间的色序不稳定性来制备亮氨酸-脑啡肽，总产率为55％。通过避免使用常见的脱保护试剂（例如三氟乙酸或哌啶），该新策略允许在基本中性的介质中制备肽。