(S)-2-[((2S,3S,6S)-6-{[(R)-3-tert-Butyldisulfanyl-2-(2-hexadecanoylamino-acetylamino)-propionylamino]-methyl}-3-hydroxy-tetrahydro-pyran-2-carbonyl)-amino]-4-methyl-pentanoic acid methyl ester | 849368-30-5

• 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)-2-[((2S,3S,6S)-6-{[(R)-3-tert-Butyldisulfanyl-2-(2-hexadecanoylamino-acetylamino)-propionylamino]-methyl}-3-hydroxy-tetrahydro-pyran-2-carbonyl)-amino]-4-methyl-pentanoic acid methyl ester
• CAS: 849368-30-5
• 化学式: C₃₉H₇₂N₄O₈S₂
• 分子量: 789.155
• InChiKey: JMXLBESYJWDHCB-IIXYZMIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  53.0
• 可旋转键数：
  28.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  172.16
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[((2S,3S,6S)-6-{[(R)-3-tert-Butyldisulfanyl-2-(2-hexadecanoylamino-acetylamino)-propionylamino]-methyl}-3-hydroxy-tetrahydro-pyran-2-carbonyl)-amino]-4-methyl-pentanoic acid methyl ester 在 lithium hydroxide 、 Tris-HCl buffer 、 DL-dithiothreitol 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 生成 (S)-2-[((2S,3S,6S)-6-{[(R)-2-(2-Hexadecanoylamino-acetylamino)-3-mercapto-propionylamino]-methyl}-3-hydroxy-tetrahydro-pyran-2-carbonyl)-amino]-4-methyl-pentanoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of lipophilic Ca1a2L analogues as potential bisubstrate inhibitors of protein:geranylgeranyl transferase-1

  摘要：

  Ca(1)a(2)L analogues, having the central dipeptide a(1)a(2) replaced by a sugar amino acid, were provided at the N-terminal end directly or via a spacer with a lipid. The inhibitory potency toward PGGT-1 of the set of lipophilic Ca(1)a(2)L analogues was improved in comparison with the original analogues, 1 and 2. The most potent inhibitors, 39 and 40, were found to inhibit PGGT-1 with an IC50-value of 12.7 and 12.3 muM, respectively, which is a 6-fold improvement over the corresponding analogue 1. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.035
• 作为产物：
  描述：

  在 三异丙基硅烷 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 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 (S)-2-[((2S,3S,6S)-6-{[(R)-3-tert-Butyldisulfanyl-2-(2-hexadecanoylamino-acetylamino)-propionylamino]-methyl}-3-hydroxy-tetrahydro-pyran-2-carbonyl)-amino]-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of lipophilic Ca1a2L analogues as potential bisubstrate inhibitors of protein:geranylgeranyl transferase-1

  摘要：

  Ca(1)a(2)L analogues, having the central dipeptide a(1)a(2) replaced by a sugar amino acid, were provided at the N-terminal end directly or via a spacer with a lipid. The inhibitory potency toward PGGT-1 of the set of lipophilic Ca(1)a(2)L analogues was improved in comparison with the original analogues, 1 and 2. The most potent inhibitors, 39 and 40, were found to inhibit PGGT-1 with an IC50-value of 12.7 and 12.3 muM, respectively, which is a 6-fold improvement over the corresponding analogue 1. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.035