2-[(2S,3S,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl]-4-hydroxy-pentanoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2-[(2S,3S,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl]-4-hydroxy-pentanoic acid
• 英文别名: 2-[(2S,3S,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]sulfanyl-4-hydroxypentanoic acid
• 化学式: C₁₈H₃₂O₁₃S
• 分子量: 488.51
• InChiKey: BMLDSPJRXYLLAS-DFWJJWFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  241
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-O-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 吡啶 、 sodium hydroxide 、 potassium nitrite 、 乙酸肼 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-[(2S,3S,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl]-4-hydroxy-pentanoic acid
  参考文献：
  名称：

  The synthesis and biological evaluation of lactose-based sialylmimetics as inhibitors of rotaviral infection

  摘要：

  Rotaviruses are the most significant cause of gastroenteritis in young children and are responsible for over 600,000 infant deaths annually. The rotaviral haemagglutinin protein (VP8*) of some strains has been implicated in early recognition and binding events of host cell-surface sialoglycoconjugates, and is therefore an attractive target for potential therapeutic intervention. Since N-acetylneuraminic acid alpha(2,3)-linked to galactose is believed to be the minimum binding epitope of rotavirus to host cells, we report here our development of an efficient and flexible synthetic route to a range of lactose-based sialylmimetics of alpha(2,3)-linked thiosialosides. These compounds were biologically evaluated as inhibitors of rotaviral infection using an in vitro neutralisation assay. The results suggest that these lactose-based sialylmimetics are not inhibitors of the rhesus rotavirus strain; however, they do exhibit modest inhibition of the human (Wa) strain, presumably through inhibition of the rotaviral adhesion process. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.057

文献信息

• Synthesis of Lactose-Based <i>S</i>-Linked Sialylmimetics of α(2,3)-Sialosides
  作者：Angela Liakatos、Milton J. Kiefel、Mark von Itzstein

  DOI：10.1021/ol035733d

  日期：2003.11.1

  A new approach toward the synthesis of lactose-based S-linked sialylmimetics of alpha(2,3)-linked sialosides is described. These compounds, represented by the general structure 3, were prepared from methyl beta-D-lactoside in 11 steps. It was found that the choice of protecting group was crucial to allow the efficient introduction of sulfur at the 3-position of the galactose ring.
• The synthesis and biological evaluation of lactose-based sialylmimetics as inhibitors of rotaviral infection
  作者：Angela Liakatos、Milton J. Kiefel、Fiona Fleming、Barbara Coulson、Mark von Itzstein

  DOI：10.1016/j.bmc.2005.08.057

  日期：2006.2

  Rotaviruses are the most significant cause of gastroenteritis in young children and are responsible for over 600,000 infant deaths annually. The rotaviral haemagglutinin protein (VP8*) of some strains has been implicated in early recognition and binding events of host cell-surface sialoglycoconjugates, and is therefore an attractive target for potential therapeutic intervention. Since N-acetylneuraminic acid alpha(2,3)-linked to galactose is believed to be the minimum binding epitope of rotavirus to host cells, we report here our development of an efficient and flexible synthetic route to a range of lactose-based sialylmimetics of alpha(2,3)-linked thiosialosides. These compounds were biologically evaluated as inhibitors of rotaviral infection using an in vitro neutralisation assay. The results suggest that these lactose-based sialylmimetics are not inhibitors of the rhesus rotavirus strain; however, they do exhibit modest inhibition of the human (Wa) strain, presumably through inhibition of the rotaviral adhesion process. (c) 2005 Elsevier Ltd. All rights reserved.