2'-azidoethyl 5-N-acetyl-α-neuraminyl-(2->6)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside | 338971-45-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-azidoethyl 5-N-acetyl-α-neuraminyl-(2->6)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-5-acetamido-6-(2-azidoethoxy)-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 338971-45-2
• 化学式: C₂₇H₄₅N₅O₁₉
• 分子量: 743.676
• InChiKey: OUVFYXXCDRESLA-ICTHHDDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  347
• 氢给体数：
  12
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  N-tetradecyl-2-propynamide 、 2'-azidoethyl 5-N-acetyl-α-neuraminyl-(2->6)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-[2-[4-(tetradecylcarbamoyl)triazol-1-yl]ethoxy]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Sugar Arrays in Microtiter Plate

  摘要：

  1,3-Dipolar cycloadditions between azides and alkynes were exploited to attach oligosaccharides to a C-14 hydrocarbon chain that noncovalently binds to the microtiter well surface. Synthesis of sugar arrays was performed on a micromolar scale in situ in the microtiter plate. As a model study, the beta-galactosyllipid 5 was displayed on a 4-mumol scale. Formation of product was confirmed via ESI-MS, and the yield was determined via chemical and biological assays. Several complex carbohydrates (6-16) were also displayed in microtiter plates and successfully screened with various lectins. Moreover, sialyl Lewis x (17) was synthesized via the enzymatic fucosylation of a precursor displayed in the plate. Studies on inhibition of this biotransformation have been carried out, and the IC50 value found for the known inhibitor 20 was consistent with previous studies in solution.

  DOI：

  10.1021/ja020887u
• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 在 β-(1->4)-galactosyltransferase 、 human α-(2->6)-sialyltransferase 、 UDP-galactose 4'-epimerase 、 sodium cacodylate 、 manganese(ll) chloride 作用下， 以 水 为溶剂， 反应 48.0h， 生成 2'-azidoethyl 5-N-acetyl-α-neuraminyl-(2->6)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Large-scale chemoenzymatic synthesis of blood group and tumor-associated poly-N-acetyllactosamine antigens

  摘要：

  Poly-N-acetyllactosamines (pLNs) are common terminal sugars of many N- and O-linked glycan structures present in glycoproteins and glycolipids. Utilizing various glycosyltransferases, we developed new and efficient chemoenzymatic methods for the synthesis of pLNs in gram-scale. Specifically, the use of sialyltransferases and fucosyltransferases enabled us to synthesize and purify 24 blood group and tumor-associated pLN derivatives with alpha-(2 -> 3)- and alpha-(2 -> 6)-linked sialic acid, as well as with alpha-(1 -> 2)- and alpha-(1 -> 3)-linked fucose. All synthesized derivatives were linked to a short 2-azidoethyl spacer for further modification. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.043

文献信息

• Fluorophore-labeled, Peptide-based Glycoclusters: Synthesis, Binding Properties for Lectins, and Detection of Carbohydrate-Binding Proteins in Cells
  作者：Xizhe Tian、Jaeyoung Pai、Kyung-Hwa Baek、Sung-Kyun Ko、Injae Shin

  DOI：10.1002/asia.201100319

  日期：2011.8.1

  different spatial arrangements of the sugar ligands were prepared. Lectin‐binding properties of the glycoclusters were initially examined by using microarrays immobilized by various lectins. These glycoclusters were then employed to detect the cell‐surface carbohydrate‐binding proteins in bacteria. Finally, the uptake of glycoclusters by mammalian cells through receptor‐mediated endocytosis was evaluated

  描述了一种简便高效的线性合成基于线性肽的糖簇的方法，该糖簇具有各种化合价和不同的糖配体空间排列方式。合成策略包括1）固相合成荧光团标记的含炔烃的肽，2）通过点击化学将叠氮化物连接的未保护的单糖，二糖和三糖偶联到固相支持物上的炔烃偶联的肽上和3）从固相支持物中释放出荧光团标记的糖团。通过使用该方法，制得了32个荧光糖簇，其化合价为1-4，糖配体的空间排列不同。糖簇的凝集素结合特性最初是通过使用各种凝集素固定化的微阵列来检查的。然后将这些糖簇用于检测细菌中的细胞表面糖结合蛋白。最后，评估了哺乳动物细胞通过受体介导的内吞作用对糖簇的吸收。从体外和体内研究获得的结果表明，对固定蛋白和细胞表面蛋白的结合亲和力高度依赖于糖簇中糖配体的化合价和空间排列。
• Synthesis of Sugar Arrays in Microtiter Plate
  作者：Fabio Fazio、Marian C. Bryan、Ola Blixt、James C. Paulson、Chi-Huey Wong

  DOI：10.1021/ja020887u

  日期：2002.12.1

  1,3-Dipolar cycloadditions between azides and alkynes were exploited to attach oligosaccharides to a C-14 hydrocarbon chain that noncovalently binds to the microtiter well surface. Synthesis of sugar arrays was performed on a micromolar scale in situ in the microtiter plate. As a model study, the beta-galactosyllipid 5 was displayed on a 4-mumol scale. Formation of product was confirmed via ESI-MS, and the yield was determined via chemical and biological assays. Several complex carbohydrates (6-16) were also displayed in microtiter plates and successfully screened with various lectins. Moreover, sialyl Lewis x (17) was synthesized via the enzymatic fucosylation of a precursor displayed in the plate. Studies on inhibition of this biotransformation have been carried out, and the IC50 value found for the known inhibitor 20 was consistent with previous studies in solution.
• Large-scale chemoenzymatic synthesis of blood group and tumor-associated poly-N-acetyllactosamine antigens
  作者：Daniela Vasiliu、Nahid Razi、Yingning Zhang、Nathan Jacobsen、Kirk Allin、Xiaofei Liu、Julia Hoffmann、Ognian Bohorov、Ola Blixt

  DOI：10.1016/j.carres.2006.03.043

  日期：2006.7

  Poly-N-acetyllactosamines (pLNs) are common terminal sugars of many N- and O-linked glycan structures present in glycoproteins and glycolipids. Utilizing various glycosyltransferases, we developed new and efficient chemoenzymatic methods for the synthesis of pLNs in gram-scale. Specifically, the use of sialyltransferases and fucosyltransferases enabled us to synthesize and purify 24 blood group and tumor-associated pLN derivatives with alpha-(2 -> 3)- and alpha-(2 -> 6)-linked sialic acid, as well as with alpha-(1 -> 2)- and alpha-(1 -> 3)-linked fucose. All synthesized derivatives were linked to a short 2-azidoethyl spacer for further modification. (c) 2006 Elsevier Ltd. All rights reserved.