N-[O-(α-D-galactopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-1-β-D-glucopyranosyl]-5-azidopentamide | 246516-70-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[O-(α-D-galactopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-1-β-D-glucopyranosyl]-5-azidopentamide
• 英文别名: 5-azido-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-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]pentanamide
• CAS: 246516-70-1
• 化学式: C₂₃H₄₀N₄O₁₆
• 分子量: 628.588
• InChiKey: KMOOFDDTIZTRSY-YOUFCGDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  292
• 氢给体数：
  11
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  N-[O-(α-D-galactopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-1-β-D-glucopyranosyl]-5-azidopentamide 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、405.3 kPa 条件下， 以100%的产率得到N-[O-(β-D-galactopyranosyl)-(1->4)-1-β-D-glucopyranosyl]-5-aminopentamide
  参考文献：
  名称：

  Enhanced Inhibition of Human Anti-Gal Antibody Binding to Mammalian Cells by Synthetic α-Gal Epitope Polymers

  摘要：

  Neoglycopolymers of polyacrylamide backbone conjugated with varying densities of Gal alpha 1-3Gal beta 1-4Glc beta trisaccharide epitopes (alpha-Gal epitopes) were designed and synthesized to study the inhibition of the binding of human natural anti-Gal antibodies to either alpha-Gal-containing glycoproteins or alpha-Gal antigens on the surface of mammalian cells. An inhibition ELISA using mouse laminin and a flow cytometry assay using pig kidney cells (PK15) were established to determine the binding affinity of the synthesized polymers. In comparison to the alpha-Gal monomer (Gal alpha 1-3Gal beta 1-4GlcNHAc beta), the alpha-Gal polymers dramatically enhanced the inhibition of human anti-Gal antibodies (IgG, IgM, and IgA) binding to mouse laminin or mammalian cells. Increases of 7.8 x 10(3)- and 5.0 x 10(4) -fold in inhibitory potential of polymer 7C to IgA and IgM (with IC(50)s of 7.0 and 5.6 nM respectively) were observed over the monomer in inhibition ELISA. The results also indicated that binding enhancement of alpha-Gal polymers is greater for anti-Gal IgA and IgM than for IgG. Such amplified binding differences among the three anti-Gal isotypes can be utilized to selectively inhibit or remove a particular isotype of anti-Gal antibodies. Moreover, it was demonstrated through the flow cytometry assay that certain alpha-Gal polymers are effective in inhibition of anti-Gal antibody (in human serum) binding to pig kidney (PK15) cells. Thus, such synthetic carbohydrate polymers may find practical applications in cell xenotransplantations.

  DOI：

  10.1021/ja990219h
• 作为产物：
  描述：

  5-氯代戊酰氯 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~70.0 ℃ 、405.3 kPa 条件下， 反应 23.0h， 生成 N-[O-(α-D-galactopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-1-β-D-glucopyranosyl]-5-azidopentamide
  参考文献：
  名称：

  Enhanced Inhibition of Human Anti-Gal Antibody Binding to Mammalian Cells by Synthetic α-Gal Epitope Polymers

  摘要：

  Neoglycopolymers of polyacrylamide backbone conjugated with varying densities of Gal alpha 1-3Gal beta 1-4Glc beta trisaccharide epitopes (alpha-Gal epitopes) were designed and synthesized to study the inhibition of the binding of human natural anti-Gal antibodies to either alpha-Gal-containing glycoproteins or alpha-Gal antigens on the surface of mammalian cells. An inhibition ELISA using mouse laminin and a flow cytometry assay using pig kidney cells (PK15) were established to determine the binding affinity of the synthesized polymers. In comparison to the alpha-Gal monomer (Gal alpha 1-3Gal beta 1-4GlcNHAc beta), the alpha-Gal polymers dramatically enhanced the inhibition of human anti-Gal antibodies (IgG, IgM, and IgA) binding to mouse laminin or mammalian cells. Increases of 7.8 x 10(3)- and 5.0 x 10(4) -fold in inhibitory potential of polymer 7C to IgA and IgM (with IC(50)s of 7.0 and 5.6 nM respectively) were observed over the monomer in inhibition ELISA. The results also indicated that binding enhancement of alpha-Gal polymers is greater for anti-Gal IgA and IgM than for IgG. Such amplified binding differences among the three anti-Gal isotypes can be utilized to selectively inhibit or remove a particular isotype of anti-Gal antibodies. Moreover, it was demonstrated through the flow cytometry assay that certain alpha-Gal polymers are effective in inhibition of anti-Gal antibody (in human serum) binding to pig kidney (PK15) cells. Thus, such synthetic carbohydrate polymers may find practical applications in cell xenotransplantations.

  DOI：

  10.1021/ja990219h

文献信息

• Efficient synthesis of globoside and isogloboside tetrasaccharides by using β(1→3) N-acetylgalactosaminyltransferase/UDP-N-acetylglucosamine C4 epimerase fusion protein
  作者：Jun Shao、Jianbo Zhang、Przemyslaw Kowal、Yuquan Lu、Peng George Wang

  DOI：10.1039/b300831b

  日期：——

  The β(1→3) N-acetylgalactosaminyltransferase/UDP-N-acetylglucosamine C4 epimerase fusion protein was constructed and used in coupled enzymatic reactions to synthesize a variety of globotetraose and isoglobotetraose derivatives from the corresponding lactoside acceptors.

  构建了β(1→3)N-乙酰半乳糖胺基转移酶/UDP-N-乙酰葡萄糖胺C4差向异构酶融合蛋白，并将其用于耦合酶促反应，以相应的乳糖苷受体为原料合成了多种四糖和异四糖衍生物。
• Enhanced Inhibition of Human Anti-Gal Antibody Binding to Mammalian Cells by Synthetic α-Gal Epitope Polymers
  作者：Jianq-Qiang Wang、Xi Chen、Wei Zhang、Sima Zacharek、Yongsheng Chen、Peng George Wang

  DOI：10.1021/ja990219h

  日期：1999.9.1

  Neoglycopolymers of polyacrylamide backbone conjugated with varying densities of Gal alpha 1-3Gal beta 1-4Glc beta trisaccharide epitopes (alpha-Gal epitopes) were designed and synthesized to study the inhibition of the binding of human natural anti-Gal antibodies to either alpha-Gal-containing glycoproteins or alpha-Gal antigens on the surface of mammalian cells. An inhibition ELISA using mouse laminin and a flow cytometry assay using pig kidney cells (PK15) were established to determine the binding affinity of the synthesized polymers. In comparison to the alpha-Gal monomer (Gal alpha 1-3Gal beta 1-4GlcNHAc beta), the alpha-Gal polymers dramatically enhanced the inhibition of human anti-Gal antibodies (IgG, IgM, and IgA) binding to mouse laminin or mammalian cells. Increases of 7.8 x 10(3)- and 5.0 x 10(4) -fold in inhibitory potential of polymer 7C to IgA and IgM (with IC(50)s of 7.0 and 5.6 nM respectively) were observed over the monomer in inhibition ELISA. The results also indicated that binding enhancement of alpha-Gal polymers is greater for anti-Gal IgA and IgM than for IgG. Such amplified binding differences among the three anti-Gal isotypes can be utilized to selectively inhibit or remove a particular isotype of anti-Gal antibodies. Moreover, it was demonstrated through the flow cytometry assay that certain alpha-Gal polymers are effective in inhibition of anti-Gal antibody (in human serum) binding to pig kidney (PK15) cells. Thus, such synthetic carbohydrate polymers may find practical applications in cell xenotransplantations.