methyl (1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronate | 501326-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronate
• CAS: 501326-64-3
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: KRZOULUBFIQZTL-UTLUCORTSA-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 (1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-D-arabino-hexopyranuronate 在 lithium hydroxide 、 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 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 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)-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 (1R)-1-cyano-1,2,3-trideoxy-D-arabino-hex-2-enopyranuronate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 24.0h， 生成 methyl (1R)-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-#

文献信息

• A Practical Synthesis of Gramicidin S and Sugar Amino Acid Containing Analogues
  作者：Gijsbert M. Grotenbreg、Martijn Kronemeijer、Mattie S. M. Timmer、Farid El Oualid、Renate M. van Well、Martijn Verdoes、Emile Spalburg、Peter A. V. van Hooft、Albert J. de Neeling、Daan Noort、Jacques H. van Boom、Gijsbert A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1021/jo0487449

  日期：2004.11.1

  practical gram-scale and high-yielding synthesis of the antimicrobial peptide gramicidin S is presented. An Fmoc-based solid-phase peptide synthesis protocol is employed for the generation of the linear decapeptide precursor, which is cyclized in solution to afford the target compound. The versatility of our method is demonstrated by the construction of eight gramicidin S analogues (15a−h) having nonproteinogenic

  提出了一种实用的克级和高收率的抗菌肽短杆菌肽S的合成方法。使用基于Fmoc的固相肽合成方案来生成线性十肽前体，将其在溶液中环化以提供目标化合物。我们的方法的通用性是由八个短杆菌肽小号类似物（施工证明15A - ħ具有nonproteinogenic糖的氨基酸残基（）4 - 7）在返回区域并入。