N-乙酰基-S-法呢基-L-半胱氨酸甲酯 | 135304-08-4

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: N-乙酰基-S-法呢基-L-半胱氨酸甲酯
• 英文名称: N-acetyl-S-farnesyl-L-cysteine methyl ester
• 英文别名: N-acetyl cysteine (S-farnesyl) methyl ester；Ac-Cys(farnesyl)-OMe；methyl (2R)-2-acetamido-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylpropanoate
• CAS: 135304-08-4
• 化学式: C₂₁H₃₅NO₃S
• 分子量: 381.58
• InChiKey: MXSBUVKSWFWHTQ-WOWWHVILSA-N

物化性质

• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 储存条件：
  应将密闭存放在-15 ºC的阴凉干燥环境中。

反应信息

• 作为反应物：
  描述：

  N-乙酰基-S-法呢基-L-半胱氨酸甲酯 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以84%的产率得到N-乙酰基-S-法呢基-L-半胱氨酸
  参考文献：
  名称：

  A Photoactivatable Prenylated Cysteine Designed to Study Isoprenoid Recognition

  摘要：

  Protein prenylation, involving the alkylation of a specific C-terminal cysteine with a C-15 or C-20 isoprenoid unit, is an essential posttranslational modification required by most GTP-binding proteins for normal biological activity. Despite the ubiquitous nature of this modification and numerous efforts aimed at inhibiting prenylating enzymes for therapeutic purposes, the function of prenylation remains unclear. To explore the role the isoprenoid plays in mediating protein-protein recognition, we have synthesized a photoactivatable, isoprenoid-containing cysteine analogue (2) designed to act as a mimic of the C-terminus of prenylated proteins. Photolysis experiments with 2 and RhoCDI (GDI), a protein which interacts with prenylated Rho proteins, suggest that the GDI is in direct contact with the isoprenoid moiety. These results, obtained using purified GDI as well as Escherichia coli (E. coli) crude extract containing GDI, suggest that this analogue will be an effective and versatile tool for the investigation of putative isoprenoid binding sites in a variety of systems. Incorporation of this analogue into peptides or proteins should allow for even more specific interactions between the photoactivatable isoprenoid and any number of isoprenoid binding proteins.

  DOI：

  10.1021/ja0012016
• 作为产物：
  描述：

  反式,反式-金合欢醇 在 四溴化碳 、 polymer supported PPh₃ 、 zinc diacetate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 29.0h， 生成 N-乙酰基-S-法呢基-L-半胱氨酸甲酯
  参考文献：
  名称：

  A Photoactivatable Prenylated Cysteine Designed to Study Isoprenoid Recognition

  摘要：

  Protein prenylation, involving the alkylation of a specific C-terminal cysteine with a C-15 or C-20 isoprenoid unit, is an essential posttranslational modification required by most GTP-binding proteins for normal biological activity. Despite the ubiquitous nature of this modification and numerous efforts aimed at inhibiting prenylating enzymes for therapeutic purposes, the function of prenylation remains unclear. To explore the role the isoprenoid plays in mediating protein-protein recognition, we have synthesized a photoactivatable, isoprenoid-containing cysteine analogue (2) designed to act as a mimic of the C-terminus of prenylated proteins. Photolysis experiments with 2 and RhoCDI (GDI), a protein which interacts with prenylated Rho proteins, suggest that the GDI is in direct contact with the isoprenoid moiety. These results, obtained using purified GDI as well as Escherichia coli (E. coli) crude extract containing GDI, suggest that this analogue will be an effective and versatile tool for the investigation of putative isoprenoid binding sites in a variety of systems. Incorporation of this analogue into peptides or proteins should allow for even more specific interactions between the photoactivatable isoprenoid and any number of isoprenoid binding proteins.

  DOI：

  10.1021/ja0012016

文献信息

• EP0527896A4
  申请人：——

  公开号：EP0527896A4

  公开（公告）日：1993-10-06
• SUBSTRATES AND INHIBITORS FOR PRENYL CYSTEINE METHYLTRANSFERASE ENZYMES
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：EP0527896A1

  公开（公告）日：1993-02-24
• US5043268A
  申请人：——

  公开号：US5043268A

  公开（公告）日：1991-08-27
• US5571687A
  申请人：——

  公开号：US5571687A

  公开（公告）日：1996-11-05
• [EN] SUBSTRATES AND INHIBITORS FOR PRENYL CYSTEINE METHYLTRANSFERASE ENZYMES
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：WO1991017261A1

  公开（公告）日：1991-11-14

  (EN) Compounds of formula (I), in which R1 is alkyl of 1 to 3 carbon atoms; R2 is -COX, wherein X is hydroxy, methyl, amino, thio, H-N-(alkyl of 1 to 3 carbon atoms), N-(alkyl of 1 to 3 carbon atoms)2, or halogen; R3 is a straight or branched chain alkyl of 10 to 25 carbon atoms, or a straight or branched chain alkene including polyunsaturated alkenes of 10 to 25 carbon atoms; and the alkali metal, alkaline earth metal, ammonium, and substituted ammonium salts thereof when R2 is -COOH, are substrates and/or inhibitors specifically for prenyl cysteine methyltransferase enzymes which catalyze the methyl transfer from S-adenosylmethionine to the C-termini of proteins and peptides with prenylated cysteine residues at their C-termini. The compounds, as substrates, are particularly suitable for use in assays for qualitatively or quantitatively detecting the farnesyl cysteine methyltransferase enzymes.(FR) Composés de la formule (I), dans laquelle: R1 représente alkyle contenant 1 à 3 atomes de carbone; R2 représente -COX, dans lequel X représente hydroxy, méthyle, amino, thio, H-N-(alkyle contenant 1 à 3 atomes de carbone), N-(alkyle contenant 1 à 3 atomes de carbone)2 ou halogène; R3 représente un alkyle à chaîne droite ou ramifiée contenant 10 à 25 atomes de carbone, ou un alcène à chaîne droite ou ramifiée, ou un alcène à chaîne droite ou ramifiée comprenant des alcènes poly-insaturés contenant 10 à 25 atomes de carbone; et le métal alcalin, le métal alcalino-terreux, l'ammonium, et ses sels d'ammonium substitués constituent spécifiquement, lorsque R2 représente -COOH, des substrats et/ou des inhibiteurs d'enzymes de méthyltransférase de cystéine de prényle, lesquelles catalysent le transfert de méthyle de S-adénosylméthionine aux C-terminaisons de protéines et de peptides présentant des résidus de cystéine prénylée au niveau de leurs C-terminaisons. Les composés, en tant que substrats, sont particulièrement adaptés à une utilisation dans des analyses permettant de détecter qualitativement ou quantitativement les enzymes de méthyltransférase de cystéine de farnésyle.