α-NVOC-tyrosine | 135997-57-8

• 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: α-NVOC-tyrosine
• 英文别名: NVOC-L-Tyr-OH
• CAS: 135997-57-8
• 化学式: C₁₉H₂₀N₂O₉
• 分子量: 420.376
• InChiKey: ALDBDIQJSDJXAF-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  157.46
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  α-NVOC-tyrosine 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(6-nitroveratryloxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(S)-tyrosine cyanomethyl ester
  参考文献：
  名称：

  Site-Specific Incorporation of Glycosylated Serine and Tyrosine Derivatives into Proteins

  摘要：

  Glycosylation of proteins can have a dramatic effect on their physical, chemical, and biological properties. Analogues of dihydrofolate reductase and firefly luciferase containing glycosylated amino acids at single, predetermined sites have been elaborated. Misacylated suppressor tRNAs activated with glycosylated serine and tyrosine derivatives were used for suppression of the nonsense codons in a cell-free protein biosynthesizing system, thereby permitting the preparation of the desired glycosylated proteins. In this fashion, it was possible to obtain proteins containing both mono- and diglycosylated amino acids, including glycosylated serine and tyrosine moieties. For the modified firefly luciferases, the effect of these substitutions on the wavelength of the light emitted by firefly luciferase was investigated. The maximum wavelength for mutants containing peracetylated glycosylated serine derivatives at position 284 showed a red shift in the emission spectra. For mutants containing glycosylated tyrosines, the red shift was observed only when the carbohydrate moiety was fully deacetylated.

  DOI：

  10.1021/ja067466n
• 作为产物：
  描述：

  在 RhCl(PPh₃)3 作用下， 以 乙醇 、 水 为溶剂， 生成 α-NVOC-tyrosine
  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

• Discovery of Small-Molecule Interleukin-2 Inhibitors from a DNA-Encoded Chemical Library
  作者：Markus Leimbacher、Yixin Zhang、Luca Mannocci、Michael Stravs、Tim Geppert、Jörg Scheuermann、Gisbert Schneider、Dario Neri

  DOI：10.1002/chem.201200952

  日期：2012.6.18

  AbstractLibraries of chemical compounds individually coupled to encoding DNA tags (DNA‐encoded chemical libraries) hold promise to facilitate exceptionally efficient ligand discovery. We constructed a high‐quality DNA‐encoded chemical library comprising 30 000 drug‐like compounds; this was screened in 170 different affinity capture experiments. High‐throughput sequencing allowed the evaluation of 120 million DNA codes for a systematic analysis of selection strategies and statistically robust identification of binding molecules. Selections performed against the tumor‐associated antigen carbonic anhydrase IX (CA IX) and the pro‐inflammatory cytokine interleukin‐2 (IL‐2) yielded potent inhibitors with exquisite target specificity. The binding mode of the revealed pharmacophore against IL‐2 was confirmed by molecular docking. Our findings suggest that DNA‐encoded chemical libraries allow the facile identification of drug‐like ligands principally to any protein of choice, including molecules capable of disrupting high‐affinity protein–protein interactions.
• Preparation of Translationally Competent tRNA by Direct Chemical Acylation
  作者：Noah H. Duffy、Dennis A. Dougherty

  DOI：10.1021/ol101408f

  日期：2010.9.3

  Nonsense codon suppression for unnatural amino acid incorporation requires the preparation of a suppressor aminoacyl-tRNA. Chemical acylation strategies are general but inefficient and arduous. A recent report (J. Am. Chem. Soc. 2007, 129, 15848) showed acylation of RNA mediated by lanthanum(III) using amino acid phosphate esters. The successful implementation of this methodology to full-length suppressor tRNA is described, and it is shown that the derived aminoacyl-tRNA is translationally competent in Xenopus oocytes.