(1R,4S,5S)-4-O-benzyl-1-{(N-[(S-(tert-butyl)sulfanyl)]-N-{[9H-fluoren-9-ylmethoxy]carbonyl}-L-cysteinyl)aminomethyl}tetrahydropyran-6-N-L-leucine methyl ester | 742102-91-6

• 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: (1R,4S,5S)-4-O-benzyl-1-{(N-[(S-(tert-butyl)sulfanyl)]-N-{[9H-fluoren-9-ylmethoxy]carbonyl}-L-cysteinyl)aminomethyl}tetrahydropyran-6-N-L-leucine methyl ester
• 英文别名: methyl (2S)-2-[[(2R,3S,6R)-6-[[[(2R)-3-(tert-butyldisulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]amino]methyl]-3-phenylmethoxyoxan-2-yl]methylamino]-4-methylpentanoate
• CAS: 742102-91-6
• 化学式: C₄₃H₅₇N₃O₇S₂
• 分子量: 792.073
• InChiKey: PBXLCFRSVDYQFL-XCCAXGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  55
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  175
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (1R,4S,5S)-4-O-benzyl-1-{(N-[(S-(tert-butyl)sulfanyl)]-N-{[9H-fluoren-9-ylmethoxy]carbonyl}-L-cysteinyl)aminomethyl}tetrahydropyran-6-N-L-leucine methyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.75h， 以67%的产率得到(1R,4S,5S)-4-O-benzyl-1-{(N-[(S-(tert-butyl)sulfanyl)]-N-{[9H-fluoren-9-ylmethoxy]carbonyl}-L-cysteinyl)aminomethyl}tetrahydropyran-6-N-L-leucine
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Su- gar Amino Acid Based Inhibitors of Pro- tein Prenyl Transferases PFT and PGGT-1

  摘要：

  Eleven analogues of the C-terminal Ca(1)a(2)X Motif found in natural substrates of the prenyl transferases PFT and PGGT-1 were synthesized and evaluated for their inhibition potency and selectivity against PFT and PGGT-1. Replacement of the central dipeptide part a(1)a(2) by a benzylated sugar amino acid resulted in a good and highly selective PFT inhibitor (8, IC50 = 250 +/- 20 nM). The methyl ester of 8 (13) selectively inhibited protein farnesylation in cultured cells.

  DOI：

  10.1021/jm049927q
• 作为产物：
  描述：

  在 N-乙基吗啉 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 苯硫酚 、 异丙硫醇 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (1R,4S,5S)-4-O-benzyl-1-{(N-[(S-(tert-butyl)sulfanyl)]-N-{[9H-fluoren-9-ylmethoxy]carbonyl}-L-cysteinyl)aminomethyl}tetrahydropyran-6-N-L-leucine methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Su- gar Amino Acid Based Inhibitors of Pro- tein Prenyl Transferases PFT and PGGT-1

  摘要：

  Eleven analogues of the C-terminal Ca(1)a(2)X Motif found in natural substrates of the prenyl transferases PFT and PGGT-1 were synthesized and evaluated for their inhibition potency and selectivity against PFT and PGGT-1. Replacement of the central dipeptide part a(1)a(2) by a benzylated sugar amino acid resulted in a good and highly selective PFT inhibitor (8, IC50 = 250 +/- 20 nM). The methyl ester of 8 (13) selectively inhibited protein farnesylation in cultured cells.

  DOI：

  10.1021/jm049927q

文献信息

• Design, Synthesis, and Evaluation of Su- gar Amino Acid Based Inhibitors of Pro- tein Prenyl Transferases PFT and PGGT-1
  作者：Farid El Oualid、Brigitte E. A. Burm、Ingrid M. Leroy、Louis H. Cohen、Jacques H. van Boom、Hans van den Elst、Herman S. Overkleeft、Gijs A. van der Marel、Mark Overhand

  DOI：10.1021/jm049927q

  日期：2004.7.1

  Eleven analogues of the C-terminal Ca(1)a(2)X Motif found in natural substrates of the prenyl transferases PFT and PGGT-1 were synthesized and evaluated for their inhibition potency and selectivity against PFT and PGGT-1. Replacement of the central dipeptide part a(1)a(2) by a benzylated sugar amino acid resulted in a good and highly selective PFT inhibitor (8, IC50 = 250 +/- 20 nM). The methyl ester of 8 (13) selectively inhibited protein farnesylation in cultured cells.