O-[β-D-galactopyranosyl(1→3)-(2-acetylamino-2-deoxy-β-D-glucopyranosyl)(1→6)-2-acetylamino-2-deoxy-α-D-galactopyranosyl]-L-threonine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-[β-D-galactopyranosyl(1→3)-(2-acetylamino-2-deoxy-β-D-glucopyranosyl)(1→6)-2-acetylamino-2-deoxy-α-D-galactopyranosyl]-L-threonine
• 英文别名: 3-O-(2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-galactopyranosyl)-L-threonine；(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5-hydroxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-aminobutanoic acid
• 化学式: C₂₆H₄₅N₃O₁₈
• 分子量: 687.653
• InChiKey: YQNQEZMFMBODFK-FPGXXZNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  339
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  cytidine-5′-monophospho-N-acetylneuraminic acid 、 O-[β-D-galactopyranosyl(1→3)-(2-acetylamino-2-deoxy-β-D-glucopyranosyl)(1→6)-2-acetylamino-2-deoxy-α-D-galactopyranosyl]-L-threonine 在 pasteurella multocida α2,3-sialyltransferase 1 M144D mutant 作用下， 以 aq. buffer 为溶剂， 反应 1.0h， 以83%的产率得到
  参考文献：
  名称：

  Diversity-Oriented Chemoenzymatic Synthesis of Sulfated and Nonsulfated Core 2 O-GalNAc Glycans

  摘要：

  DOI：

  10.1021/acs.joc.1c01115
• 作为产物：
  描述：

  在 sodium hydroxide 、 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 2.33h， 生成 O-[β-D-galactopyranosyl(1→3)-(2-acetylamino-2-deoxy-β-D-glucopyranosyl)(1→6)-2-acetylamino-2-deoxy-α-D-galactopyranosyl]-L-threonine
  参考文献：
  名称：

  Mucin type glycopeptides: Synthesis of Core 2, Core 6 and F1-α building blocks and some unexpected reactions

  摘要：

  DOI：

  10.1016/s0040-4039(96)02252-6

文献信息

• Efficient synthesis of core 2 class glycosyl amino acids by one-pot glycosylation approach
  作者：Hiroshi Tanaka、Masaatsu Adachi、Takashi Takahashi

  DOI：10.1016/j.tetlet.2003.12.042

  日期：2004.2

  We describe the one-pot synthesis of core 2 class branched oligosaccharides initiated by chemo-selective glycosylation of silyl anther. Glycosylation of 6-O-silyl-4-benzyl-2-azido-thiogalactoside with glycosyl fluoride provided selectively 6-glycosylated thioglycoside without both O-glycosylation at the 3 position and S-glycosylation. Subsequent coupling of galactosyl fluoride and amino acids afforded the protected branched oligosaccharides in good yields. (C) 2003 Elsevier Ltd. All rights reserved.