methyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl-(1[*]4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 172950-32-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl-(1[*]4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 172950-32-2
• 化学式: C₄₁H₄₄N₄O₁₄
• 分子量: 816.819
• InChiKey: XATBGCFXMLAKJX-PDLLLZHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  59.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  220.42
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  methyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl-(1[*]4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 乙二胺 、 正丁醇 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Methyl 3-amino-3-deoxy-β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-β-d-glucopyranoside: An inhibitor of UDP-d-galactose: β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-d-glucose(1 → 3)-α-d-galactopyranosyltransferase

  摘要：

  UDP-D-galactose: beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-D-glucose alpha(1 --> 3)-D-galactopyranosyltransferase [E.C. 2.4.1.151] transfers D-galactosyl-residues from the sugar nucleotide with retention of configuration. We report here that synthetic methyl 3'-amino-3'-deoxy-N-acetyllactosaminide (9), where the hydroxyl group normally undergoing galactosylation has been replaced by amino group, is an inhibitor for this enzyme with K-i = 104 mu M. The mode of inhibition is not competitive, but appears to be specific, since other glycosyltransferases were not affected by 9.

  DOI：

  10.1016/0008-6215(95)00165-p
• 作为产物：
  描述：

  甲基 3,6-二-O-苄基-2-脱氧-2-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)吡喃己糖苷 、 2,4,6-tri-O-acetyl-3-azido-α-D-galactopyranosyl bromide 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以82%的产率得到methyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl-(1[*]4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Methyl 3-amino-3-deoxy-β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-β-d-glucopyranoside: An inhibitor of UDP-d-galactose: β-d-galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-d-glucose(1 → 3)-α-d-galactopyranosyltransferase

  摘要：

  UDP-D-galactose: beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-D-glucose alpha(1 --> 3)-D-galactopyranosyltransferase [E.C. 2.4.1.151] transfers D-galactosyl-residues from the sugar nucleotide with retention of configuration. We report here that synthetic methyl 3'-amino-3'-deoxy-N-acetyllactosaminide (9), where the hydroxyl group normally undergoing galactosylation has been replaced by amino group, is an inhibitor for this enzyme with K-i = 104 mu M. The mode of inhibition is not competitive, but appears to be specific, since other glycosyltransferases were not affected by 9.

  DOI：

  10.1016/0008-6215(95)00165-p