1-azidopropyl 3,4,6,-tri-O-[(β-D-gulcopyranosyl)-1''H-1'',2'',3''-triazol-1''-ylmethyl]-2-acetamido-2-deoxy-β-D-glucopyranoside | 1393736-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-azidopropyl 3,4,6,-tri-O-[(β-D-gulcopyranosyl)-1''H-1'',2'',3''-triazol-1''-ylmethyl]-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-(3-azidopropoxy)-4,5-bis[[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]triazol-4-yl]methoxy]-6-[[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]triazol-4-yl]methoxymethyl]oxan-3-yl]acetamide
• CAS: 1393736-29-2
• 化学式: C₃₈H₅₉N₁₃O₂₁
• 分子量: 1033.96
• InChiKey: RBYZEZLJJRWYRM-JACAGTRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.5
• 重原子数：
  72
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  452
• 氢给体数：
  13
• 氢受体数：
  29

反应信息

• 作为产物：
  描述：

  1-azidopropyl 3,4,6,-tri-O-[(,2'3',4',6'-tetra-O-acetyl-β-D-gulcopyranosyl)-1''H-1'',2'',3''-triazol-1''-ylmethyl]-2-acetamido-2-deoxy-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以95%的产率得到1-azidopropyl 3,4,6,-tri-O-[(β-D-gulcopyranosyl)-1''H-1'',2'',3''-triazol-1''-ylmethyl]-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Multivalent Neoglyconjugates of MUC1 by the Conjugation of Carbohydrate-Centered, Triazole-Linked Glycoclusters to MUC1 Peptides Using Click Chemistry

  摘要：

  The efficient synthesis of multivalent neoglycoconjugates of MUC1 is reported, which utilizes Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuACC) of azide-functionalized GIcNAc-centered neoglycotetrasaccharide clusters to the MUC1 peptide sequence that was equipped with a propargylglycine residue for "click chemistry". In turn the azido-GIcNAc-centered neoglycoclusters were assembled by reaction of a GIcNAc core containing peripheral propargyl funclionalities with an appropriate azido-functionalized monosaccharide. The resulting suitably substituted tetrasaccharyl triazole cluster can be easily appended to a range of acetylene-functionalized peptides to produce neoglycoconjugates of biologically important glycopeptides. As proof of principle, the click neoglycoclusters prepared herein were ligated to the MUC1 peptide sequence.

  DOI：

  10.1021/jo3013435

文献信息

• Synthesis of Multivalent Neoglyconjugates of MUC1 by the Conjugation of Carbohydrate-Centered, Triazole-Linked Glycoclusters to MUC1 Peptides Using Click Chemistry
  作者：Dong Jun Lee、Sung-Hyun Yang、Geoffrey M. Williams、Margaret A. Brimble

  DOI：10.1021/jo3013435

  日期：2012.9.7

  The efficient synthesis of multivalent neoglycoconjugates of MUC1 is reported, which utilizes Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuACC) of azide-functionalized GIcNAc-centered neoglycotetrasaccharide clusters to the MUC1 peptide sequence that was equipped with a propargylglycine residue for "click chemistry". In turn the azido-GIcNAc-centered neoglycoclusters were assembled by reaction of a GIcNAc core containing peripheral propargyl funclionalities with an appropriate azido-functionalized monosaccharide. The resulting suitably substituted tetrasaccharyl triazole cluster can be easily appended to a range of acetylene-functionalized peptides to produce neoglycoconjugates of biologically important glycopeptides. As proof of principle, the click neoglycoclusters prepared herein were ligated to the MUC1 peptide sequence.