S-(4-fluorophenyl)-L-cysteine | 331-90-8

• 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: S-(4-fluorophenyl)-L-cysteine
• 英文别名: S-(4-fluoro-phenyl)-L-cysteine；S-(4-Fluor-phenyl)-L-cystein；(R)-2-Amino-3-(4-fluor-phenylmercapto)-propionsaeure；3-(p-fluorophenylthio) alanine；(2R)-2-amino-3-(4-fluorophenyl)sulfanylpropanoic acid
• CAS: 331-90-8
• 化学式: C₉H₁₀FNO₂S
• 分子量: 215.248
• InChiKey: FYPZDFGIJISTBF-QMMMGPOBSA-N

物化性质

• 熔点：
  179-181 °C (decomp)
• 沸点：
  362.4±42.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  S-(4-fluorophenyl)-L-cysteine 在 双氧水 、 溶剂黄146 作用下， 生成 (R)-2-amino-3-(4-fluoro-benzenesulfonyl)-propionic acid
  参考文献：
  名称：

  Potential Anticancer Agents. V. Some Sulfur-Substituted Derivatives of Cysteine¹

  摘要：

  DOI：

  10.1021/jo01103a004
• 作为产物：
  描述：

  L-胱氨酸 在 copper(I) oxide 、 硫酸 、 锌 作用下， 生成 S-(4-fluorophenyl)-L-cysteine
  参考文献：
  名称：

  Zbarsky; Young, Journal of Biological Chemistry, 1944, vol. 152, p. 599,600

  摘要：

  DOI：

文献信息

• Expanding the Structural Diversity of Protein Building Blocks with Noncanonical Amino Acids Biosynthesized from Aromatic Thiols
  作者：Yong Wang、Xiaoxu Chen、Wenkang Cai、Linzhi Tan、Yutong Yu、Boyang Han、Yuxuan Li、Yuanzhe Xie、Yeyu Su、Xiaozhou Luo、Tao Liu

  DOI：10.1002/anie.202014540

  日期：2021.4.26

  accessible aromatic thiols. We demonstrate that nearly 50 ncAAs with a diverse array of structures can be biosynthesized from these simple small‐molecule precursors by hijacking the cysteine biosynthetic enzymes, and the resulting ncAAs can subsequently be incorporated into proteins via an expanded genetic code. Moreover, we demonstrate that bioorthogonal reactive groups such as aromatic azides and

  将结构新颖的非规范氨基酸 (ncAAs) 结合到蛋白质中对于科学和生物医学应用都很有价值。为了扩大可用 ncAAs 的结构多样性并减轻化学合成它们的负担，我们开发了一种通用且简单的生物合成方法，通过用经济的市售或合成可获得的芳香硫醇喂养细胞，将新型 ncAAs 基因编码为重组蛋白。我们证明，通过劫持半胱氨酸生物合成酶，可以从这些简单的小分子前体生物合成近 50 种具有多种结构的 ncAAs，随后可以通过扩展的遗传密码将生成的 ncAAs 整合到蛋白质中。而且，
• Reaction of [18F]4-fluorobenzenediazonium cations with cysteine or the cysteinyl group: preparation of18F-labeled S-aryl-cysteine and a radiolabeled peptide
  作者：J. T. Patt、M. Patt

  DOI：10.1002/jlcr.635

  日期：2002.12

  A reaction route for the preparation of no-carrier-added (n.c.a.) [18F]S-4-fluorophenylcysteine 7 via the [18F]-4-fluorobenzenediazonium ion 4 is described. The key step in this radiosynthesis is the reaction of 4 with cysteine forming [18F]4-fluorophenyldiazocysteine 6, which is subsequently converted into 7 by irradiation with 366 nm light. 4 was synthesized by reacting 1,4-dinitrobenzene 1 with [18F]-fluoride in acetonitrile in a PEEK-capillary in a microwave oven. After dilution of the reaction mixture with methanol, the resulting [18F]4-fluoro-1-nitrobenzene 2 was submitted to reduction by means of H2 with Pd on C catalyst. The resulting [18F]4-fluoroaniline 3 was purified by HPLC and diazotized to 4. The preparation of 4 was optimized with regard to yield and purity. The radiochemical yield of 6 was >90% (based on 3) while after UV irradiation and HPLC purification 45% of 7 (based on 3) was obtained (yields corrected for decay). The suitability of this method for labeling peptides with fluorine-18 was demonstrated by application to the tripeptide, glutathione (GSH; γ-L-glutamyl-L-cysteinyglycine) 8. Copyright © 2002 John Wiley & Sons, Ltd.

  描述了一种通过[18F]-4-氟苯二氮离子4制备无载体添加（n.c.a.）[18F]S-4-氟苯丙氨酸7的反应路线。本放射合成的关键步骤是4与半胱氨酸反应形成[18F]4-氟苯基二氮半胱氨酸6，随后通过366纳米光照射转化为7。4的合成是通过将1,4-二硝基苯1与[18F]-氟化物在微波炉中的PEEK毛细管中于乙腈中反应得到的。在用甲醇稀释反应混合物后，得到的[18F]4-氟-1-硝基苯2通过Pd/C催化剂与氢气还原。得到的[18F]4-氟苯胺3经过HPLC纯化并重氮化为4。4的制备在产率和纯度上得到了优化。6的放射化学产率超过90%（基于3），而在紫外线照射和HPLC纯化后，获得了7的产率为45%（基于3，已校正衰变）。通过应用于三肽谷胱甘肽（GSH；γ-L-谷氨酸-L-半胱氨酸-甘氨酸）8，证明了该方法在用氟-18标记肽类方面的适用性。版权 © 2002 John Wiley & Sons, Ltd.
• MANAGEMENT OF VASCULAR ACCESS IN EUROPE: PART 2 - A MULTI CENTRE STUDY OF RELATED COMPLICATIONS
  作者：Monique M. Elseviers、Jean-Pierre Waeleghem、Elizabeth Lindley

  DOI：10.1111/j.1755-6686.2003.tb00272.x

  日期：2003.1.3

  SUMMARYIntroduction | The pilot project of the Research Board of EDTNA/ERCA handled the management of vascular accesses (VA) in European dialysis centres. In the first part of the study, centre policies related to VA management were investigated. This paper reports on the second part of the project, investigating VA related complications reported during an observational prospective study.Methods | A cohort of 1380 adult patients, randomly selected in 47 centres out of 16 European countries were followed during one year using a computerised data collection system. Data were collected at baseline, after six and 12 months and each time a VA complication occurred.Results | At the start of the observation period, 77% had a native AV fistula, 10% had an AV graft and 13% a catheter. A total of 489 complications were noted. Most frequently observed were thrombosis, stenosis, infection, bleeding and flow problems. Hospitalisation (mean duration=6.2 days) was required in 39% of complications and 29% of complications resulted in a definitive loss of VA. Complications were more frequently observed in catheters (27%) and AV grafts (37%) compared to AV fistulae (15%). When compared with AV fistulae, the risk for thrombosis was more than four times higher and for bleeding more than six times higher if an AV graft was used. Catheters showed an eightfold increased risk to develop infections and flow problems.Conclusion | This study revealed the high complication rate in VA and strengthened the actions to promote AV fistulae as first choice VA.
• US3950542A
  申请人：——

  公开号：US3950542A

  公开（公告）日：1976-04-13
• US3976781A
  申请人：——

  公开号：US3976781A

  公开（公告）日：1976-08-24