methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-S-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate | 112697-41-3

• 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: methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-S-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-acetylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 112697-41-3
• 化学式: C₂₂H₃₁NO₁₃S
• 分子量: 549.553
• InChiKey: ZQTVFTACJQPOSW-ZJGVECAJSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  632.6±55.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  212
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-S-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以80%的产率得到methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate
  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：

  N-acetyl neuraminic acid 在 三氟化硼乙醚 、 氢氟酸 、 caesium carbonate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-S-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate
  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+

文献信息

• Synthesis of soluble multivalent glycoconjugates that target the Hc region of botulinum neurotoxin A
  作者：Ramesh R. Kale、Colin M. Clancy、Rebecca M. Vermillion、Eric A. Johnson、Suri S. Iyer

  DOI：10.1016/j.bmcl.2007.02.028

  日期：2007.5

  The design, synthesis, and initial inhibitory studies of di- and tetravalent glycoconjugates that target the heavy chain of botulinum neurotoxin A are reported. (C) 2007 Elsevier Ltd. All rights reserved.
• XASEHGAVA, AKIRA;KISO, MAKOTO
  作者：XASEHGAVA, AKIRA、KISO, MAKOTO

  DOI：——

  日期：——