N¹,N¹⁷-di-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,6,9,12,15-pentaoxaheptadecanediamide | 1016647-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N¹,N¹⁷-di-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,6,9,12,15-pentaoxaheptadecanediamide
• 英文别名: N-[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]-3-[2-[2-[2-[2-[3-[[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanamide
• CAS: 1016647-10-1
• 化学式: C₄₆H₈₀N₆O₂₇
• 分子量: 1149.17
• InChiKey: NRSRMJOPTTWTRJ-YRODSAIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.6
• 重原子数：
  79
• 可旋转键数：
  32
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  478
• 氢给体数：
  16
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  N,N'-diacetylchitobiosamine 、 4,7,10,13,16-五氧杂十九烷二酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 以60%的产率得到N¹,N¹⁷-di-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,6,9,12,15-pentaoxaheptadecanediamide
  参考文献：
  名称：

  Efficient synthesis of spacer-N-linked double-headed glycosides carrying N-acetylglucosamine and N,N′-diacetylchitobiose and their cross-linking activities with wheat germ agglutinin

  摘要：

  We describe here an efficient synthetic route to spacer-N-linked double-headed glycosides via a simple two-step procedure. N-Acetylglucosamine (GlcNAc) and N,N'-diacetylchitobiose [(GlcNAC)(2)] were treated with ammonia and the resulting N-beta-glycosylamines were coupled to a series of dicarboxylic acids. Condensation with each dicarboxylic acid proceeded stereoselectively to give the corresponding beta-N-linked double-headed glycoside without the need for any protection/deprotection steps. Interaction of the resulting N-linked double-headed glycosides with wheat germ agglutinin (WGA) were then investigated using a precipitation assay and an optical biosensor based on surface plasmon resonance (SPR). Spacer-N-linked double-headed glycosides bearing GlcNAc and (GlcNAC)(2) were found to be capable of binding and precipitating WGA as divalent ligands. However, the length of the spacer groups between the two terminal sugar residues was found to greatly influence the cross-linking activities with the lectin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.11.025

文献信息

• Efficient synthesis of spacer-N-linked double-headed glycosides carrying N-acetylglucosamine and N,N′-diacetylchitobiose and their cross-linking activities with wheat germ agglutinin
  作者：Yoshinori Misawa、Ryuichi Masaka、Kayo Maeda、Megumi Yano、Takeomi Murata、Hirokazu Kawagishi、Taichi Usui

  DOI：10.1016/j.carres.2007.11.025

  日期：2008.2

  We describe here an efficient synthetic route to spacer-N-linked double-headed glycosides via a simple two-step procedure. N-Acetylglucosamine (GlcNAc) and N,N'-diacetylchitobiose [(GlcNAC)(2)] were treated with ammonia and the resulting N-beta-glycosylamines were coupled to a series of dicarboxylic acids. Condensation with each dicarboxylic acid proceeded stereoselectively to give the corresponding beta-N-linked double-headed glycoside without the need for any protection/deprotection steps. Interaction of the resulting N-linked double-headed glycosides with wheat germ agglutinin (WGA) were then investigated using a precipitation assay and an optical biosensor based on surface plasmon resonance (SPR). Spacer-N-linked double-headed glycosides bearing GlcNAc and (GlcNAC)(2) were found to be capable of binding and precipitating WGA as divalent ligands. However, the length of the spacer groups between the two terminal sugar residues was found to greatly influence the cross-linking activities with the lectin. (c) 2007 Elsevier Ltd. All rights reserved.