3-propenyl (2',3'-O,N⁴-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate | 302346-93-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 3-propenyl (2',3'-O,N⁴-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[[(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methoxy-prop-2-enoxyphosphoryl]sulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 302346-93-6
• 化学式: C₅₃H₅₇N₄O₂₂PS
• 分子量: 1165.09
• InChiKey: QLZUJOFTVYYGRB-WFCOYNRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  81
• 可旋转键数：
  31
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  354
• 氢给体数：
  2
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  3-propenyl (2',3'-O,N⁴-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate 在 四(三苯基膦)钯 potassium 2pethylhexanoate 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 disodium cytidine-5'-yl 5-acetamido-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2-yl phosphorothioate
  参考文献：
  名称：

  Synthesis and Characterization of an Anomeric Sulfur Analogue of CMP-Sialic Acid

  摘要：

  alpha-2,3-Sialyltransferase catalyzes the transfer of sialic acid from CMP-sialic acid (1) to a lactose acceptor. An analogue of 1 was synthesized in which the anomeric oxygen atom was replaced with a sulfur atom (1S). The key step in the synthesis of 1S was a tetrazole-promoted coupling of a cytidine-5'-phosphoramidite with a glycosyl thiol of a protected sialic acid. Compounds 1 and 1S were characterized for their activity in a sialyl transfer assay. The rate of solvolysis in aqueous buffer of analogue 1S was 50-fold slower than that of 1. Analogue 1S was found to be substrate for alpha-2,3-sialyltransferase. The K-m of 1S was just 3-fold higher than that of 1, while the k(cat) of 1S was 2 orders of magnitude lower compared to 1.

  DOI：

  10.1021/jo000646+
• 作为产物：
  描述：

  胞苷 在 咪唑 、 四氮唑 、 二异丙基铵盐四氮唑 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 57.0h， 生成 3-propenyl (2',3'-O,N⁴-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate
  参考文献：
  名称：

  Synthesis and Characterization of an Anomeric Sulfur Analogue of CMP-Sialic Acid

  摘要：

  alpha-2,3-Sialyltransferase catalyzes the transfer of sialic acid from CMP-sialic acid (1) to a lactose acceptor. An analogue of 1 was synthesized in which the anomeric oxygen atom was replaced with a sulfur atom (1S). The key step in the synthesis of 1S was a tetrazole-promoted coupling of a cytidine-5'-phosphoramidite with a glycosyl thiol of a protected sialic acid. Compounds 1 and 1S were characterized for their activity in a sialyl transfer assay. The rate of solvolysis in aqueous buffer of analogue 1S was 50-fold slower than that of 1. Analogue 1S was found to be substrate for alpha-2,3-sialyltransferase. The K-m of 1S was just 3-fold higher than that of 1, while the k(cat) of 1S was 2 orders of magnitude lower compared to 1.

  DOI：

  10.1021/jo000646+