(S)-2-Amino-3-pentafluorophenyl-propionic acid methyl ester | 198701-52-9

• 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)-2-Amino-3-pentafluorophenyl-propionic acid methyl ester
• 英文别名: methyl (2S)-2-amino-3-(2,3,4,5,6-pentafluorophenyl)propanoate
• CAS: 198701-52-9
• 化学式: C₁₀H₈F₅NO₂
• 分子量: 269.171
• InChiKey: UXYISCHKMSZLBW-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-3-pentafluorophenyl-propionic acid methyl ester 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 98.0h， 生成 Fmoc-DOPA(ac)-(F₅)Phe(1)-(F₅)Phe(2)-COOMe
  参考文献：
  名称：

  Self-assembly of a tripeptide into a functional coating that resists fouling

  摘要：

  一种短肽（三肽）可以自组装成具有抗污染活性的超分子功能涂层。这种涂层在需要避免蛋白质、细菌和其他生物吸附的应用中非常有用。

  DOI：

  10.1039/c4cc03578j
• 作为产物：
  描述：

  Boc-pentafluoro-L-Phe 在 氯化亚砜 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-2-Amino-3-pentafluorophenyl-propionic acid methyl ester
  参考文献：
  名称：

  Self-assembly of a tripeptide into a functional coating that resists fouling

  摘要：

  一种短肽（三肽）可以自组装成具有抗污染活性的超分子功能涂层。这种涂层在需要避免蛋白质、细菌和其他生物吸附的应用中非常有用。

  DOI：

  10.1039/c4cc03578j

文献信息

• Stabilizing and Destabilizing Effects of Phenylalanine → F₅-Phenylalanine Mutations on the Folding of a Small Protein
  作者：Matthew G. Woll、Erik B. Hadley、Sandro Mecozzi、Samuel H. Gellman

  DOI：10.1021/ja0634573

  日期：2006.12.1

  --> F5-Phe) mutants for the 35-residue chicken villin headpiece subdomain (c-VHP), the hydrophobic core of which features a cluster of three Phe side chains (residues 6, 10, and 17). Phe --> F5-Phe mutations are interesting because aryl-perfluoroaryl interactions of optimal geometry are intrinsically more favorable than aryl-aryl interactions and because perfluoroaryl units are more hydrophobic than are

  我们报告了苯丙氨酸到五氟苯丙氨酸 (Phe --> F5-Phe) 突变体的 35 个残留鸡绒毛头饰子域 (c-VHP) 的系统评估，其疏水核心具有三个 Phe 侧链的簇（残基 6、10 和 17)。Phe --> F5-Phe 突变很有趣，因为最佳几何形状的芳基-全氟芳基相互作用本质上比芳基-芳基相互作用更有利，并且因为全氟芳基单元比类似的芳基单元更疏水。一种突变体 Phe-10 --> F5-Phe 提供了相对于天然序列增强的三级结构稳定性。分析的其他六个突变体导致稳定性下降。
• Chemical and Biological Evaluation of Dipeptidyl Boronic Acid Proteasome Inhibitors for Use in Prodrugs and Pro-Soft Drugs Targeting Solid Tumors
  作者：Lawrence J. Milo、Jack H. Lai、Wengen Wu、Yuxin Liu、Hlaing Maw、Youhua Li、Zhiping Jin、Ying Shu、Sarah E. Poplawski、Yong Wu、David G. Sanford、James L. Sudmeier、William W. Bachovchin

  DOI：10.1021/jm200460q

  日期：2011.7.14

  Bortezomib, a dipeptidyl boronic acid and potent inhibitor of the 26S proteasome, is remarkably effective against multiple myeloma (MM) but not against solid tumors. Dose-limiting adverse effects from "on target" inhibition of the proteasome in normal cells and tissues appear to be a key obstacle. Achieving efficacy against solid tumors therefore is likely to require making the inhibitor more selective for tumor tissue over normal tissues. The simplest strategy that might provide such tissue specificity would be to employ a tumor specific protease to release an inhibitor from a larger, noninhibitory structure. However, such release would necessarily generate an inhibitor with a free N-terminal amino group, raising a key question: Can short peptide boronic acids with N-terminal amino groups have the requisite properties to serve as warheads in prodrugs? Here we show that dipeptides of boroLeu, the smallest plausible candidates for the task, can indeed be sufficiently potent, cell-penetrating, cytotoxic, and stable to degradation by cellular peptidases to serve in this capacity.
• Synthesis of a Series of Stromelysin-Selective Thiadiazole Urea Matrix Metalloproteinase Inhibitors
  作者：E. Jon Jacobsen、Mark A. Mitchell、Susan K. Hendges、Kenneth L. Belonga、Louis L. Skaletzky、Lindsay S. Stelzer、Thomas. J. Lindberg、Edward L. Fritzen、Heinrich J. Schostarez、Theresa J. O'Sullivan、Linda L. Maggiora、Christopher W. Stuchly、Alice L. Laborde、Marc F. Kubicek、Roger A. Poorman、Joan M. Beck、Henry R. Miller、Gary L. Petzold、Pam S. Scott、Scott E. Truesdell、Tanya L. Wallace、John W. Wilks、Christopher Fisher、Linda V. Goodman、Paul S. Kaytes、Stephen R. Ledbetter、Elaine A. Powers、Gabriel Vogeli、John E. Mott、Catherine M. Trepod、Douglas J. Staples、Eric T. Baldwin、Barry C. Finzel

  DOI：10.1021/jm9803222

  日期：1999.5.1

  The synthesis and enzyme inhibition data for a series of thiadiazole urea matrix metalloproteinase (MMP) inhibitors are described. A broad screening effort was utilized to identify several thiadiazoles which were weak inhibitors of stromelysin. Optimization of the thiadiazole leads to include an alpha-amino acid side chain with variable terminal amide substituents provided a series of ureas which were moderately effective stromelysin inhibitors, with K-i's between 0.3 and 1.0 mu M. The most effective analogues utilized an L-phenylalanine as the amino acid component. In particular, unsubstituted 46 had a K-i of 710 nM, while the p-fluoro analogue 52 displayed increased potency (100 nM). Stromelysin inhibition was further improved using a pentafluorophenylalanine substituent which resulted in 70, a 14 nM inhibitor. While gelatinase inhibition was generally poor, the use of 1-(2-pyridyl)piperazine as the amide component usually provided for enhanced activity, with 71 inhibiting gelatinase with a K-i of 770 nM. The combination of this heterocycle with a p-fluorophenylalanine substituent provided the only analogue, 69, with collagenase activity (13 mu M). The SAR for analogues described within this series can be rationalized through consideration of the X-ray structure recently attained for 70 complexed to stromelysin. Uniquely, this structure showed the inhibitor to be completely orientated on the left side of the enzyme cleft. These results suggest that thiadiazole urea heterocycles which incorporate a substituted phenylalanine can provide selective inhibitors of stromelysin. Careful selection of the amide substituent can also provide for analogues with modest gelatinase inhibition.
• Self-assembly of a tripeptide into a functional coating that resists fouling
  作者：Sibaprasad Maity、Sivan Nir、Tal Zada、Meital Reches

  DOI：10.1039/c4cc03578j

  日期：——

  A short peptide (tripeptide) self-assembles into a supramolecular functional coating with antifouling activity. This coating can be useful in applications where the adsorption of proteins, bacteria and other organisms should be avoided.

  一种短肽（三肽）可以自组装成具有抗污染活性的超分子功能涂层。这种涂层在需要避免蛋白质、细菌和其他生物吸附的应用中非常有用。