O-(β-D-galactopyranosyl)-(1->4)-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-(β-D-galactopyranosyl)-(1->4)-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: Gal(b1-4)GlcN(b1-3)Gal(b1-4)Glc(b)-N3；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-amino-6-[(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-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₄H₄₂N₄O₁₉
• 分子量: 690.613
• InChiKey: MHNVVFDSTKHQPB-DVCKEHJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.2
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  348
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 O-(β-D-galactopyranosyl)-(1->4)-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosyl azide hydrochloride 在 苯磺酰胺 、 Tris-HCl buffer 、 GalE-GalT 、 manganese(ll) chloride 作用下， 以 水 为溶剂， 反应 72.0h， 以87%的产率得到O-(α-D-galactopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-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
• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(3,6-di-O-acetyl-2-phthalimido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl azide hydrochloride 在 甲胺 作用下， 以 水 为溶剂， 反应 12.0h， 以92%的产率得到O-(β-D-galactopyranosyl)-(1->4)-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.