[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2S)-2-[(2-azidoacetyl)amino]-3-[[(2S,3S)-1-[[(2S,3S)-1-[[(2S,3R)-3-hydroxy-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-oxopropoxy]oxan-2-yl]methyl acetate | 1186298-09-8

• 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: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2S)-2-[(2-azidoacetyl)amino]-3-[[(2S,3S)-1-[[(2S,3S)-1-[[(2S,3R)-3-hydroxy-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-oxopropoxy]oxan-2-yl]methyl acetate
• CAS: 1186298-09-8
• 化学式: C₄₄H₇₁N₉O₁₇
• 分子量: 998.098
• InChiKey: FKQCMYMQAXIBKA-AXRHLODHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  70
• 可旋转键数：
  31
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  336
• 氢给体数：
  7
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2S)-2-[(2-azidoacetyl)amino]-3-[[(2S,3S)-1-[[(2S,3S)-1-[[(2S,3R)-3-hydroxy-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-oxopropoxy]oxan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以41%的产率得到Az-Ser(OGlcNAc)-Ile-Ile-Thr-LeuEK
  参考文献：
  名称：

  O-GlcNAc Peptide Epoxyketones Are Recognized by Mammalian Proteasomes

  摘要：

  Cytosolic and nuclear proteins may be subject to both O-GlcNAcylation and proteasomal degradation. By means of activity-based profiling, we demonstrate that O-GlcNAc serine-containing peptide epoxyketones bind to the proteasome catalytic active sites and thus provide the first clear evidence that proteasomes recognize peptides post-translationally modified with a GlcNAc moiety.

  DOI：

  10.1021/ja901231w
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以26%的产率得到[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2S)-2-[(2-azidoacetyl)amino]-3-[[(2S,3S)-1-[[(2S,3S)-1-[[(2S,3R)-3-hydroxy-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-oxopropoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  O-GlcNAc Peptide Epoxyketones Are Recognized by Mammalian Proteasomes

  摘要：

  Cytosolic and nuclear proteins may be subject to both O-GlcNAcylation and proteasomal degradation. By means of activity-based profiling, we demonstrate that O-GlcNAc serine-containing peptide epoxyketones bind to the proteasome catalytic active sites and thus provide the first clear evidence that proteasomes recognize peptides post-translationally modified with a GlcNAc moiety.

  DOI：

  10.1021/ja901231w