N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-6-oxo-D-arabino-hexapyranos-6-yl]-D-leucine methyl ester | 501326-70-1

• 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-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-6-oxo-D-arabino-hexapyranos-6-yl]-D-leucine methyl ester
• 英文别名: methyl (2R)-2-[[(2S,3S,6R)-3-hydroxy-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]oxane-2-carbonyl]amino]-4-methylpentanoate
• CAS: 501326-70-1
• 化学式: C₁₉H₃₄N₂O₇
• 分子量: 402.488
• InChiKey: DGBIRKVIMJQWJZ-KBXIAJHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  123.19
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-6-oxo-D-arabino-hexapyranos-6-yl]-D-leucine methyl ester 在 三异丙基硅烷 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-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 N-((1R)-1-{[N-(S-[(tert-butyl)sulfanyl]-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl)amino]methyl}-1,2,3-trideoxy-6-oxo-D-arabino-hexopyranos-6-yl)-D-leucine methyl ester
  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-#
• 作为产物：
  描述：

  methyl (1RS)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronate 在 lithium 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 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-6-oxo-D-arabino-hexapyranos-6-yl]-D-leucine methyl ester
  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-#