O-(2-amino-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosyl azide hydrochloride

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2-amino-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosyl azide hydrochloride
• 英文别名: [(2S,3R,4R,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-azido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]azanium;chloride
• 化学式: C₁₈H₃₂N₄O₁₄*ClH
• 分子量: 564.931
• InChiKey: AEWAXBBFLXCNRB-HSFGPMSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.0
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  270
• 氢给体数：
  10
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 在 2,3,5-三甲基吡啶 、 4 Angstroem MS 、 silver trifluoromethanesulfonate 、 甲胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 O-(2-amino-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosyl azide hydrochloride
  参考文献：
  名称：

  A Unique Chemoenzymatic Synthesis of α-Galactosyl Epitope Derivatives Containing Free Amino Groups:  Efficient Separation and Further Manipulation

  摘要：

  A novel. chemoenzymatic approach for the synthesis of oligosacchrides containing free amino groups has been developed in which thermophilic glycosidases and a fusion enzyme containing catalytic domains of uridine-5'-diphospho-galactose 4-epimerase and alpha(1-->3) galactosyltransferase were used. This methodology, in conjunction with a convenient purification procedure employing ion exchange chromatography, facilitates the lengthy and high-cost process of carbohydrate synthesis. The prepared oligosaccharides range from disaccharide lactosamine (1a), trisaccharide alpha-Gal-(1-->3)-beta-Gal-(1-->4)-GlcNH(2) (2), tetrasaccharide beta-Gal-(1-->4)-beta-GlcNH(2)-(1-->3)-beta-Gal-(1-->4)-beta-Glc-N-3 (7), to pentasaccharide alpha-Gal-(1-->3)-beta-Gal-(1-->4)-beta-GlcNH(2)-(1-->3)-beta-Gal-(1-->4)-beta-Glc-N-3 (15). Compounds 2 and 15 are derivatives of natural alpha-Gal epitopes. Both of them have shown comparable activities with their natural parent compounds toward human anti-Gal IgG. This method provides a practical approach for the preparation and purification of oligosaccharides containing free amino groups, which can be further derivatized for the enhancement of biological activities.

  DOI：

  10.1021/jo990159y

文献信息

• A Unique Chemoenzymatic Synthesis of α-Galactosyl Epitope Derivatives Containing Free Amino Groups:  Efficient Separation and Further Manipulation
  作者：Jianwen Fang、Xi Chen、Wei Zhang、Jianqiang Wang、Peter R. Andreana、Peng George Wang

  DOI：10.1021/jo990159y

  日期：1999.5.1

  A novel. chemoenzymatic approach for the synthesis of oligosacchrides containing free amino groups has been developed in which thermophilic glycosidases and a fusion enzyme containing catalytic domains of uridine-5'-diphospho-galactose 4-epimerase and alpha(1-->3) galactosyltransferase were used. This methodology, in conjunction with a convenient purification procedure employing ion exchange chromatography, facilitates the lengthy and high-cost process of carbohydrate synthesis. The prepared oligosaccharides range from disaccharide lactosamine (1a), trisaccharide alpha-Gal-(1-->3)-beta-Gal-(1-->4)-GlcNH(2) (2), tetrasaccharide beta-Gal-(1-->4)-beta-GlcNH(2)-(1-->3)-beta-Gal-(1-->4)-beta-Glc-N-3 (7), to pentasaccharide alpha-Gal-(1-->3)-beta-Gal-(1-->4)-beta-GlcNH(2)-(1-->3)-beta-Gal-(1-->4)-beta-Glc-N-3 (15). Compounds 2 and 15 are derivatives of natural alpha-Gal epitopes. Both of them have shown comparable activities with their natural parent compounds toward human anti-Gal IgG. This method provides a practical approach for the preparation and purification of oligosaccharides containing free amino groups, which can be further derivatized for the enhancement of biological activities.