(S,E)-2-((tert-butoxycarbonyl)amino)-3-(4-(phenyldiazenyl)phenyl)propanoic acid | 906734-92-7

• 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: (S,E)-2-((tert-butoxycarbonyl)amino)-3-(4-(phenyldiazenyl)phenyl)propanoic acid
• CAS: 906734-92-7
• 化学式: C₂₀H₂₃N₃O₄
• 分子量: 369.42
• InChiKey: AGILQBLNBVSUCR-AWZKZOKMSA-N

物化性质

• 沸点：
  563.1±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  100.35
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S,E)-2-((tert-butoxycarbonyl)amino)-3-(4-(phenyldiazenyl)phenyl)propanoic acid 在 N-甲基吗啉 、 deoxyribonucleic acid sodium salt from herring testes 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium chloride 作用下， 以 二氯甲烷 、 重水 、 N,N-二甲基甲酰胺 、 仲丁醇 为溶剂， 反应 6.75h， 生成 (3S,6S)-3-(4-aminobutyl)-6-{4-[(E)-phenyldiazenyl]benzyl}piperazine-2,5-dione
  参考文献：
  名称：

  Photoresponsive self-healing supramolecular hydrogels for light-induced release of DNA and doxorubicin

  摘要：

  生物聚合物和生物活性小分子与含有偶氮苯基的环二肽PAP-DKP-Lys形成的水凝胶一起释放出来。

  DOI：

  10.1039/c5cc09633b
• 作为产物：
  描述：

  Boc-4-氨基-L-苯丙氨酸 、 亚硝基苯 以 溶剂黄146 为溶剂， 反应 72.0h， 以83%的产率得到(S,E)-2-((tert-butoxycarbonyl)amino)-3-(4-(phenyldiazenyl)phenyl)propanoic acid
  参考文献：
  名称：

  Photoresponsive self-healing supramolecular hydrogels for light-induced release of DNA and doxorubicin

  摘要：

  生物聚合物和生物活性小分子与含有偶氮苯基的环二肽PAP-DKP-Lys形成的水凝胶一起释放出来。

  DOI：

  10.1039/c5cc09633b

文献信息

• Azobenzene-containing photoswitchable proteasome inhibitors with selective activity and cellular toxicity
  作者：Beatriz Blanco、Kathryn A. Palasis、Alaknanda Adwal、David F. Callen、Andrew D. Abell

  DOI：10.1016/j.bmc.2017.06.011

  日期：2017.10

  A series of azobenzene-containing peptidic boronate esters was prepared and the activity of the thermally adapted states (TAS), enriched in trans isomer, and the photostationary states (PSS), enriched in cis isomer, for each compound were evaluated against β5 and β1 proteasome subunits. Compounds with a sterically demanding phenyl-substituted azobenzene at P2 (4c), and a less sterically demanding unsubstituted

  制备了一系列含偶氮苯的肽硼酸酯，并针对每种化合物针对β5和β1评估了富含反式异构体的热适应态（TAS）和富含顺式异构体的光平稳态（PSS）的活性。蛋白酶体亚基。在P2（4c）处具有空间要求的苯基取代的偶氮苯，而在N端（5a）具有较低空间要求的未取代的偶氮苯的化合物显示出两种状态之间最大的活性差异。在这两种情况下，活性更高的反式富集的TAS的活性均与硼替佐米和地兰佐米相当。此外，富含顺式的4c抑制了乳腺癌和结直肠癌细胞系中的肿瘤生长。值得注意的是，最初的4c反式富集TAS对非恶性MCF-10A细胞没有细胞毒性。
• Modulating the Phe–Phe dipeptide aggregation landscape via covalent attachment of an azobenzene photoswitch
  作者：Melby Johny、Kanchustambham Vijayalakshmi、Ankita Das、Palas Roy、Aseem Mishra、Jyotishman Dasgupta

  DOI：10.1039/c7cc04106c

  日期：——

  Synthetic control of peptide-based supramolecular assemblies can provide molecular cues to understand protein aggregation while also inspiring the development of novel chemical biology tools to deliver cargoes inside cells. Here we show that the trans-to-cis photoisomerization of a pendant azo-group covalently attached to a Phe–Phe dipeptide can comprehensively ‘turn-off’ its native fibrillation propensity

  对基于肽的超分子组装体的合成控制可以提供分子线索来理解蛋白质的聚集，同时也可以激发新型化学生物学工具的发展，从而将货物运送到细胞内。在这里，我们表明，反式-到-顺式的侧偶氮基团的光异构化共价连接到的Phe-PHE二肽能够全面“关断”其天然原纤化倾向以及提供一种光学手柄可逆地从切换聚合形态原纤维到囊泡。
• Light Regulation of Enzyme Allostery through Photo-responsive Unnatural Amino Acids
  作者：Andrea C. Kneuttinger、Kristina Straub、Philipp Bittner、Nadja A. Simeth、Astrid Bruckmann、Florian Busch、Chitra Rajendran、Enrico Hupfeld、Vicki H. Wysocki、Dominik Horinek、Burkhard König、Rainer Merkl、Reinhard Sterner

  DOI：10.1016/j.chembiol.2019.08.006

  日期：2019.11

  Imidazole glycerol phosphate synthase (ImGPS) is an allosteric bienzyme complex in which substrate binding to the synthase subunit HisF stimulates the glutaminase subunit HisH. To control this stimulation with light, we have incorporated the photo-responsive unnatural amino acids phenylalanine-4'-azobenzene (AzoF), o-nitropiperonyl-O-tyrosine (NPY), and methyl-o-nitropiperonyllysine (mNPK) at strategic positions of HisF. The light-mediated isomerization of AzoF at position 55 (fS55AzoF(E) <-> fS55AzoF(Z)) resulted in a reversible 10-fold regulation of HisH activity. The light-mediated decaging of NPY at position 39 (fY39NPY -> fY39) and of mNPK at position 99 (fK99mNPK -> fK99) led to a 4- to 6-fold increase of HisH activity. Molecular dynamics simulations explained how the unnatural amino acids interfere with the allosteric machinery of ImGPS and revealed additional aspects of HisH stimulation in wild-type ImGPS. Our findings show that unnatural amino acids can be used as a powerful tool for the spatio-temporal control of a central metabolic enzyme complex by light.
• The Incorporation of a Photoisomerizable Amino Acid into Proteins in <i>E. </i><i>c</i><i>oli</i>
  作者：Mohua Bose、Dan Groff、Jianming Xie、Eric Brustad、Peter G. Schultz

  DOI：10.1021/ja055467u

  日期：2006.1.1

  An orthogonal aminoacyl tRNA synthetase/tRNA pair has been evolved that allows the incorporation of the photoisomerizable amino acid phenylalanine-4'-azobenzene (AzoPhe) into proteins in E. coli in response to the amber nonsense codon. Further, we show that AzoPhe can be used to photoregulate the binding affinity of catabolite activator protein to its promoter. The ability to selectively incorporate AzoPhe into proteins at defined sites should make it possible to regulate a variety of biological processes with light, including enzyme, receptor, and ion channel activity.