(1S)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronic acid | 229473-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronic acid
• CAS: 229473-43-2
• 化学式: C₁₂H₂₁NO₆
• 分子量: 275.302
• InChiKey: PGLNZSFCOXNORL-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  105.09
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronic acid 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， 反应 0.5h， 生成 N-((1S)-1-{[N-(S-[(tert-butyl)sulfanyl]-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-D-cysteinyl)amino]methyl}-1,2,3-trideoxy-6-oxo-D-arabino-hexapyranos-6-yl)-L-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 (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-#

文献信息

• Design and synthesis of a protein:Farnesyltransferase inhibitor based on sugar amino acids
  作者：Herman S Overkleeft、Steven H.L Verhelst、Elsbet Pieterman、Nico J Meeuwenoord、Mark Overhand、Louis H Cohen、Gijs A van der Marel、Jacques H van Boom

  DOI：10.1016/s0040-4039(99)00697-8

  日期：1999.5

  The synthesis of four partially deoxygenated gluconic amino acids from fully acetylated D-glucal is described. Replacement of the central AA dipeptide in the CAAX tetrapeptide corresponding to the C-terminus of K-Ras p21 by one of these sugar amino acid building blocks led to a novel protein:farnesyl transferase inhibitor.

  描述了从完全乙酰化的D-葡萄糖合成四个部分脱氧的葡萄糖氨基酸。这些糖氨基酸构件之一取代了对应于K-Ras p21 C末端的CAAX四肽中的中央AA二肽，导致了一种新型的蛋白质：法呢基转移酶抑制剂。