azide α-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-2-acetamido-2-deoxyl-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: azide α-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-2-acetamido-2-deoxyl-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: Gal(a1-3)Gal(b1-4)GlcNAc(b1-3)Gal(b1-4)Glc(b)-N3；N-[(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-5-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₃₂H₅₄N₄O₂₅
• 分子量: 894.793
• InChiKey: PXADAAAMXPDVAA-WYRCBURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.5
• 重原子数：
  61
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  430
• 氢给体数：
  16
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  D-吡喃葡萄糖 、 GlcNAcβ1,3Galβ1,3GlcN3 在 α-1,3-galactosyltransferase 、 α-1,4-galactosyltransferase 、 5’-三磷酸腺苷 作用下， 以 水 为溶剂， 反应 96.0h， 以76%的产率得到azide α-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-2-acetamido-2-deoxyl-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  糖核苷酸再生珠（超级珠）：用于实际合成寡糖的多功能工具

  摘要：

  Xi Chen、Jianwen Fang、Jianbo Zhang、Ziye Liu、Jun Shao、Przemyslaw Kowal、Peter Andreana 和 Peng George Wang* 密歇根州底特律韦恩州立大学化学系 48202 接收日期 2000 年 10 月 27 日 碳水化合物在现代医学中的应用受到大多数生物学上重要的糖缀合物的高成本合成的限制。人们普遍认为糖基转移酶催化的糖基化是最实用的方法之一。1

  DOI：

  10.1021/ja005738v

文献信息

• Highly Efficient Chemoenzymatic Synthesis of α-Galactosyl Epitopes with a Recombinant α(1→3)-Galactosyltransferase
  作者：Jianwen Fang、Jun Li、Xi Chen、Yingnan Zhang、Jianqiang Wang、Zhengmao Guo、Wei Zhang、Libing Yu、Keith Brew、Peng George Wang

  DOI：10.1021/ja9808898

  日期：1998.6.13

  alpha-Galactosyl epitopes are carbohydrate structures bearing a Gal alpha 1-3Gal beta terminus. The interaction of these epitopes on the surface of animal cells with anti-alpha-galactosyl antibodies in human serum is believed to be the main cause in antibody-mediated hyperacute rejection in xenotransplantation. This report describes an efficient chemoenzymatic approach based on the use of recombinant alpha(1 --> 3)-galactosyltransferase (alpha 1,3-GalT) for the synthesis of xenoactive alpha-galactosyl epitopes, which are highly desired in the research of xenotransplantation and immunotherapy. A truncated bovine alpha 1,3-GalT (80-368) was cloned into the pET15b vector-and Subsequently transformed into E. coli BL21 strain. This expression system efficiently produced the soluble recombinant enzyme on a large scale with highly specific activity. A variety of alpha(1 --> 3)galactosylated epitopes were synthesized using such a recombinant enzyme. In a unique fashion, alpha-galactosyl pentasaccharide was synthesized via a one-pot, two-step enzymatic synthesis with in situ cofactor regeneration.