N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-methoxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide | 704905-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-methoxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
• CAS: 704905-91-9
• 化学式: C₁₆H₂₉NO₁₁
• 分子量: 411.406
• InChiKey: RHZZTOCGEJEAEQ-NSSUFJHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.95
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  176.4
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  cytidine-5'-monophosphono-N-acetylneuraminic acid 、 N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-methoxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide 在 recombinant rat liver α-2,6-sialyltransferase 作用下， 生成
  参考文献：
  名称：

  Glycosyltransferase activity can be selectively modulated by chemical modifications of acceptor substrates

  摘要：

  A range of N-acetyllactosamine derivatives, which are modified by a wide range of functionalities at C-2' and C-6, have been synthesised and the kinetic parameters of transfer catalysed by recombinant alpha-2,6-sialyltransferase and alpha-1,3-fucoyltransferase VI determined. Several of the chemical modifications led to selective modulate the activity the enzymes and offer promising lead compounds for the development of oligosaccharide primers for selective metabolic inhibition of oligosaccharide biosynthesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.024
• 作为产物：
  描述：

  methyl 2-acetamido-2-deoxy-3-O-benzyl-6-O-tert-butyldimethylsilyl-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 palladium on activated charcoal barium dihydroxide 、 tetrafluoroboric acid 、 氢气 、 sodium methylate 、 barium(II) oxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.0h， 生成 N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-methoxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Glycosyltransferase activity can be selectively modulated by chemical modifications of acceptor substrates

  摘要：

  A range of N-acetyllactosamine derivatives, which are modified by a wide range of functionalities at C-2' and C-6, have been synthesised and the kinetic parameters of transfer catalysed by recombinant alpha-2,6-sialyltransferase and alpha-1,3-fucoyltransferase VI determined. Several of the chemical modifications led to selective modulate the activity the enzymes and offer promising lead compounds for the development of oligosaccharide primers for selective metabolic inhibition of oligosaccharide biosynthesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.024

文献信息

• Novel aspects of interaction between UDP-Gal and GlcNAc β-1,4-Galactosyltransferase: Transferability and remarkable inhibitory activity of UDP-(mono-O-methylated Gal), UDP-Fuc and UDP-Man
  作者：Tsuyoshi Endo、Yasuhiro Kajihara、Hisashi Kodama、Hironobu Hashimoto

  DOI：10.1016/s0968-0896(96)00176-9

  日期：1996.11

  Four mono-O-methylated and one mono-O-acetylated UDP-D-Gal analogues and UDP-L-Fuc were synthesized. 2-O-Methyl-D-galactose residue was enzymatically transferred to give 2'-O-methyIlactosaminide in high yield. UDP-Fuc and UDP-Man showed potent inhibitory activities against beta-1,4-galactosyltransferase. Structural requirement and steric allowance for the ground and transition states of the enzyme reaction were discussed. Copyright (C) 1996 Elsevier Science Ltd