(1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester | 742102-84-7

• 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: (1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester
• 英文别名: methyl (2S)-2-[[(2R,3S,6S)-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3-phenylmethoxyoxan-2-yl]methylamino]-4-methylsulfanylbutanoate
• CAS: 742102-84-7
• 化学式: C₂₅H₄₀N₂O₆S
• 分子量: 496.668
• InChiKey: MBCLJWWKHPLRSX-MYGLTJDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine methyl ester 在 N-乙基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 异丙硫醇 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,4S,5S)-4-O-benzyl-1-{(N-[(S-(tert-butyl)sulfanyl)]-N-{[9H-fluoren-9-ylmethoxy]carbonyl}-L-cysteinyl)aminomethyl}tetrahydropyran-6-N-L-methionine 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
• 作为产物：
  描述：

  2,3-dideoxy-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-α-D-glucopyranose 在 potassium carbonate 、 苯硫酚 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 (1S,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}tetrahydropyran-6-N-L-methionine 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.