O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl azide | 226707-99-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl azide
• 英文别名: Bz(-2)[Bz(-6)]Gal(b1-4)[Bz(-2)][Bz(-3)][Bz(-6)]Glc(b)-N3；[(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-azido-4,5-dibenzoyloxy-2-(benzoyloxymethyl)oxan-3-yl]oxy-5-benzoyloxy-3,4-dihydroxyoxan-2-yl]methyl benzoate
• CAS: 226707-99-9
• 化学式: C₄₇H₄₁N₃O₁₅
• 分子量: 887.854
• InChiKey: SNRFGQQZHMMYBI-HVCKJNOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  65
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  214
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  O-<(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl>trichloracetimidat 、 O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl azide 在 4 Angstroem MS 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到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
  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-(3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosyl azide 在 溶剂黄146 作用下， 以 吡啶 、 水 为溶剂， 反应 17.0h， 生成 O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl azide
  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.