allyl α-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl α-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: Gal(a1-3)Gal(b1-4)GlcNAc(b)-O-allyl；N-[(2R,3R,4R,5S,6R)-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)-2-prop-2-enoxyoxan-3-yl]acetamide
• 化学式: C₂₃H₃₉NO₁₆
• 分子量: 585.56
• InChiKey: JLDVLSBSOZNEKI-ZLZYVOTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  267
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 Galβ1,4GlcNAcβ-O-allyl 在 Tris-HCl buffer 、 α(1->3)-galactosyltransferase 、 UDP-galactose-4-epimerase 、 manganese(ll) chloride 、 bovine serum albumin 作用下， 反应 72.0h， 以67%的产率得到allyl α-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Highly Efficient Chemoenzymatic Synthesis of α-Galactosyl Epitopes with a Recombinant α(1→3)-Galactosyltransferase

  摘要：

  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.

  DOI：

  10.1021/ja9808898

文献信息

• Synthesis of α-Gal epitope derivatives with a galactosyltransferase–epimerase fusion enzyme
  作者：Jianwen Fang、Xi Chen、Wei Zhang、Adam Janczuk、Peng George Wang

  DOI：10.1016/s0008-6215(00)00245-7

  日期：2000.12

  beta -Gal epitopes are carbohydrate structures bearing an alpha -D-Galp-(1 --> 3)-beta -D-Galp terminus and are the main cause of antibody-mediated hyperacute rejection in xenotransplantation. Nine monosaccharides and ten disaccharides were evaluated as substrates for a fusion protein, which contains both alpha-(1 --> 3)-galactosyltransferase and uridine-5'-diphosphogalactose 4-epimerase. Four disaccharide and six trisaccharide alpha -Gal epitope derivatives were synthesized utilizing this novel fusion enzyme. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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.