(R)-2-acetamido-3-((4-fluorophenyl)thio)propanoic acid | 331-93-1

• 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: (R)-2-acetamido-3-((4-fluorophenyl)thio)propanoic acid
• 英文别名: N-acetyl-S-(4-fluorophenyl)-L-cysteine；N-Acetyl-S-(4-fluor-phenyl)-L-cystein；(R)-2-Acetamino-3-(4-fluor-phenylmercapto)-propionsaeure；N-Acetyl-S-(4-fluorophenyl)cysteine；(2R)-2-acetamido-3-(4-fluorophenyl)sulfanylpropanoic acid
• CAS: 331-93-1
• 化学式: C₁₁H₁₂FNO₃S
• 分子量: 257.286
• InChiKey: MMFMNCSNACXBFZ-JTQLQIEISA-N

物化性质

• 熔点：
  161-162°C
• 沸点：
  494.6±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.7
• 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：

  (R)-2-acetamido-3-((4-fluorophenyl)thio)propanoic acid 在 硫酸 作用下， 生成 S-(4-fluorophenyl)-L-cysteine
  参考文献：
  名称：

  MANAGEMENT OF VASCULAR ACCESS IN EUROPE: PART 2 - A MULTI CENTRE STUDY OF RELATED COMPLICATIONS

  摘要：

  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.

  DOI：

  10.1111/j.1755-6686.2003.tb00272.x
• 作为产物：
  描述：

  N-乙酰-L-半胱氨酸 、 对氟碘苯 在 C₅₃H₄₆NO₄PPdS 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.1h， 以99%的产率得到(R)-2-acetamido-3-((4-fluorophenyl)thio)propanoic acid
  参考文献：
  名称：

  室温下钯催化的半胱氨酸分子的化学选择性和生物相容性官能化

  摘要：

  第三代氨基联苯Palladacycle的前催化剂“ G3-Xantphos”使含有半胱氨酸的肽能够以高收率进行功能化。共轭（生物共轭）是在生物相容性条件下于室温下化学选择性发生的。将方法扩展至蛋白质功能化可实现曲妥珠单抗抗体的选择性生物缀合。

  DOI：

  10.1002/chem.201602277

文献信息

• Metal-Free <i>S</i>-Arylation of Cysteine Using Arenediazonium Salts
  作者：Naganaboina Naveen、Saumitra Sengupta、Srinivasan Chandrasekaran

  DOI：10.1021/acs.joc.7b03160

  日期：2018.4.6

  A mild chemoselective method for S-arylation of cysteine has been developed in an open-flask procedure under metal-free conditions using arenediazonium salts in methanol.

  已经开发了在无金属条件下使用甲醇中的芳烃重氮盐盐在开瓶程序中进行半胱氨酸S芳基化的温和化学选择性方法。
• Zbarsky; Young, Journal of Biological Chemistry, 1944, vol. 152, p. 599,600
  作者：Zbarsky、Young

  DOI：——

  日期：——
• Palladium-Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine-Containing Molecules at Room Temperature
  作者：Riyadh Ahmed Atto Al-Shuaeeb、Sergii Kolodych、Oleksandr Koniev、Sébastien Delacroix、Stéphane Erb、Stéphanie Nicolaÿ、Jean-Christophe Cintrat、Jean-Daniel Brion、Sarah Cianférani、Mouâd Alami、Alain Wagner、Samir Messaoudi

  DOI：10.1002/chem.201602277

  日期：2016.8.1

  generation of aminobiphenyl palladacycle pre‐catalyst “G3‐Xantphos” enables functionalization of peptides containing cysteine in high yields. The conjugation (bioconjugation) occurs chemoselectively at room temperature under biocompatible conditions. Extension of the method to protein functionalization allows selective bioconjugation of the trastuzumab antibody.

  第三代氨基联苯Palladacycle的前催化剂“ G3-Xantphos”使含有半胱氨酸的肽能够以高收率进行功能化。共轭（生物共轭）是在生物相容性条件下于室温下化学选择性发生的。将方法扩展至蛋白质功能化可实现曲妥珠单抗抗体的选择性生物缀合。
• 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.