methyl 4-O-(6-O-(N-acetyl-α-D-neuraminate-2-yl)-β-D-galactopyranosyl)-β-D-glucopyranoside | 100605-29-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-(6-O-(N-acetyl-α-D-neuraminate-2-yl)-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: Neu5Acα(2-6)Gal(1-4)Glc-β-Me；NeuAc(a2-6)Gal(b1-4)b-Glc1Me；(2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 100605-29-6
• 化学式: C₂₄H₄₁NO₁₉
• 分子量: 647.585
• InChiKey: ISMFYEIFMJVUKD-FGRJGYJASA-N

物化性质

• 沸点：
  1089.9±65.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -7.2
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  324
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  N-乙酰神经氨酸 、 methyl 4-O-(6-O-(N-acetyl-α-D-neuraminate-2-yl)-β-D-galactopyranosyl)-β-D-glucopyranoside 在 α2,8-sialyltransferase from Campylobacter jejuni 、 Neisseria meningitides CMP-Sia synthetase 、 magnesium 、 胞苷-5’-三磷酸 作用下， 以 aq. acetate buffer 为溶剂， 生成
  参考文献：
  名称：

  Two-Step Chemoenzymatic Detection of N-Acetylneuraminic Acid−α(2-3)-Galactose Glycans

  摘要：

  Sialic acids are typically linked alpha(2-3) or alpha(2-6) to the galactose that located at the non-reducing terminal end of glycans, playing important but distinct roles in a variety of biological and pathological processes. However, details about their respective roles are still largely unknown due to the lack of an effective analytical technique. Herein, a two-step chemoenzymatic approach for the rapid and sensitive detection of N-acetylneuraminic acid-alpha(2-3)-galactose glycans is described.

  DOI：

  10.1021/jacs.6b07132
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4-tri-O-benzoyl-6-O-(methyl 4,7,8,9-tetra-O-acetyl-N-acetyl-α-D-neuraminate-2-yl)-β-D-galactopyranosyl)-β-D-glucopyranoside 在 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 1,4-二氧六环 为溶剂， 以99%的产率得到methyl 4-O-(6-O-(N-acetyl-α-D-neuraminate-2-yl)-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Design and synthesis of a multivalent homing device for targeting to murine CD22

  摘要：

  CD22 is a cell-surface glycoprotein uniquely located on mature B-cells and B-cell derived tumour cells. Current evidence suggests that binding of endogenous ligands to CD22 leads to modulation of B-cell activation by antigen. Incidentally, however, B-cell activation may derail, and lead to an undesired immune response, for example in cases of allergy, rheumatoid arthritis and Crohn's disease. In this situation, synthetic high-affinity ligands for CD22 may be of therapeutic value as inhibitors of B-cell activation. Recent studies have revealed that natural ligands for CD22 contain the trisaccharide NeuAc alpha -2,6-Lac as the basic binding motif. In addition, it has been demonstrated that binding to CD22 is strongly enhanced by multivalent presentation of the basic binding motif (cluster effect). In this paper, the stepwise development of a novel multivalent high-affinity ligand for CD22 is described. In the first stage, a series of monovalent NeuAc alpha -2,6-Glc(Y)X type binding motifs was prepared, and their affinity for murine CD22 was monitored, to obtain more insight into the effect of separate structure elements on ligand recognition. In the second stage, we prepared a trivalent cluster, based on the monovalent motif that displayed the highest affinity for CD22, NeuAccc2,6-GlcNBzNO(2)OMe (7). This cluster, TRIS(NeuAc alpha -2,6-GlcNBzNO(2))(3) (52), displayed a more than 58-fold higher affinity for CD22 than the reference structure NeuAc alpha -2,6-LacOMe (10). To our knowledge, the cluster 52 is one of the most potent antagonists for CD22, yet synthesised. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00224-8

文献信息

• Thiem, Joachim; Sauerbrei, Bernd, Angewandte Chemie, 1991, vol. 103, # 11, p. 1521 - 1523
  作者：Thiem, Joachim、Sauerbrei, Bernd

  DOI：——

  日期：——
• Design and synthesis of a multivalent homing device for targeting to murine CD22
  作者：Leo A.J.M. Sliedregt、Sabine M.W. van Rossenberg、Reshma Autar、A.Rob P.M. Valentijn、Gijs A. van der Marel、Jacques H. van Boom、Christina Piperi、P. Anton van der Merwe、Johan Kuiper、Theo J.C. van Berkel、Erik A.L. Biessen

  DOI：10.1016/s0968-0896(00)00224-8

  日期：2001.1

  CD22 is a cell-surface glycoprotein uniquely located on mature B-cells and B-cell derived tumour cells. Current evidence suggests that binding of endogenous ligands to CD22 leads to modulation of B-cell activation by antigen. Incidentally, however, B-cell activation may derail, and lead to an undesired immune response, for example in cases of allergy, rheumatoid arthritis and Crohn's disease. In this situation, synthetic high-affinity ligands for CD22 may be of therapeutic value as inhibitors of B-cell activation. Recent studies have revealed that natural ligands for CD22 contain the trisaccharide NeuAc alpha -2,6-Lac as the basic binding motif. In addition, it has been demonstrated that binding to CD22 is strongly enhanced by multivalent presentation of the basic binding motif (cluster effect). In this paper, the stepwise development of a novel multivalent high-affinity ligand for CD22 is described. In the first stage, a series of monovalent NeuAc alpha -2,6-Glc(Y)X type binding motifs was prepared, and their affinity for murine CD22 was monitored, to obtain more insight into the effect of separate structure elements on ligand recognition. In the second stage, we prepared a trivalent cluster, based on the monovalent motif that displayed the highest affinity for CD22, NeuAccc2,6-GlcNBzNO(2)OMe (7). This cluster, TRIS(NeuAc alpha -2,6-GlcNBzNO(2))(3) (52), displayed a more than 58-fold higher affinity for CD22 than the reference structure NeuAc alpha -2,6-LacOMe (10). To our knowledge, the cluster 52 is one of the most potent antagonists for CD22, yet synthesised. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Two-Step Chemoenzymatic Detection of <i>N</i>-Acetylneuraminic Acid−α(2-3)-Galactose Glycans
  作者：Liuqing Wen、Yuan Zheng、Kuan Jiang、Mingzhen Zhang、Shukkoor Muhammed Kondengaden、Shanshan Li、Kenneth Huang、Jing Li、Jing Song、Peng George Wang

  DOI：10.1021/jacs.6b07132

  日期：2016.9.14

  Sialic acids are typically linked alpha(2-3) or alpha(2-6) to the galactose that located at the non-reducing terminal end of glycans, playing important but distinct roles in a variety of biological and pathological processes. However, details about their respective roles are still largely unknown due to the lack of an effective analytical technique. Herein, a two-step chemoenzymatic approach for the rapid and sensitive detection of N-acetylneuraminic acid-alpha(2-3)-galactose glycans is described.