methyl (1S)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronate | 501326-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1S)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronate
• CAS: 501326-62-1
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: KRZOULUBFIQZTL-GUBZILKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  94.09
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (1S)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronate 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (1S)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronic acid
  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)-4-O-acetyl-1-cyano-1,2,3-trideoxy-D-arabino-hex-2-enopyranuronate 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 60.0 ℃ 、310.0 kPa 条件下， 反应 29.0h， 生成 methyl (1S)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronate
  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-#