N-{(1R)-1-[(N-{S-[(tert-butyl)sulfanyl]-L-cysteinyl}amino)methyl]-1,2,3-trideoxy-6-oxo-D-arabino-hexopyranos-6-yl}-D-leucine

• 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: N-{(1R)-1-[(N-{S-[(tert-butyl)sulfanyl]-L-cysteinyl}amino)methyl]-1,2,3-trideoxy-6-oxo-D-arabino-hexopyranos-6-yl}-D-leucine
• 英文别名: (2R)-2-[[(2S,3S,6R)-6-[[[(2R)-2-amino-3-(tert-butyldisulfanyl)propanoyl]amino]methyl]-3-hydroxyoxane-2-carbonyl]amino]-4-methylpentanoic acid
• 化学式: C₂₀H₃₇N₃O₆S₂
• 分子量: 479.662
• InChiKey: BJTIOQXBCJKUGN-LEOABGAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  202
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  亚芴甲氧羰基半胱胺酸 在 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-{(1R)-1-[(N-{S-[(tert-butyl)sulfanyl]-L-cysteinyl}amino)methyl]-1,2,3-trideoxy-6-oxo-D-arabino-hexopyranos-6-yl}-D-leucine
  参考文献：
  名称：

  蛋白质的合成和生物学评价：基于 CaaX 盒的香叶基香叶基转移酶 I 抑制剂：糖氨基酸作为二肽等排体的结合

  摘要：

  Two orthogonally protected SAA building blocks were used in the synthesis of eight novel analogues of the CaaX motif present in the natural substrates of protein:geranylgeranyltransferase I (PGGT 1), an enzyme involved in the post-translation at modification of oncogenic proteins, e.g., Ras K-4B. Remarkably, two compounds, which are stereochemically different at the C(F) position of the SAA residue and at C(2) of the Cys residue, showed comparable activity in a PGGT-1 assay. Our results indicate that both (1,5-cis) and (1,5-trans) SAA building blocks can be used for the development of novel PGGT I inhibitors.

  DOI：

  10.1002/1522-2675(200210)85:10<3455::aid-hlca3455>3.0.co;2-#

文献信息

• Synthesis and Biological Evaluation of Protein:Geranylgeranyltransferase I Inhibitors Based on the CaaX Box: Incorporation of Sugar Amino Acids as Dipeptide Isosters
  作者：Farid El Oualid、Leon Bruining、Ingrid M. Leroy、Louis H. Cohen、Jacques H. van Boom、Gijs A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1002/1522-2675(200210)85:10<3455::aid-hlca3455>3.0.co;2-#

  日期：2002.10

  Two orthogonally protected SAA building blocks were used in the synthesis of eight novel analogues of the CaaX motif present in the natural substrates of protein:geranylgeranyltransferase I (PGGT 1), an enzyme involved in the post-translation at modification of oncogenic proteins, e.g., Ras K-4B. Remarkably, two compounds, which are stereochemically different at the C(F) position of the SAA residue and at C(2) of the Cys residue, showed comparable activity in a PGGT-1 assay. Our results indicate that both (1,5-cis) and (1,5-trans) SAA building blocks can be used for the development of novel PGGT I inhibitors.