2-萘基甲基 2-乙酰氨基-2-脱氧吡喃己糖苷 | 197574-95-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-萘基甲基 2-乙酰氨基-2-脱氧吡喃己糖苷
• 中文别名: 2-萘基甲基2-乙酰氨基-2-脱氧吡喃己糖苷
• 英文名称: 2-naphthylmethyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: β-O-(2-naphthylmethyl)-GlcNAc；β-O-NAP-GlcNAc；2-Naphthylmethyl 2-acetamido-2-deoxy-b-D-glucopyranoside；N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(naphthalen-2-ylmethoxy)oxan-3-yl]acetamide
• CAS: 197574-95-1
• 化学式: C₁₉H₂₃NO₆
• 分子量: 361.395
• InChiKey: PJTVPDFSOUPHFE-FVVUREQNSA-N

物化性质

• 沸点：
  670.3±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-萘基甲基 2-乙酰氨基-2-脱氧吡喃己糖苷 在 硫酸 、 sodium hydride 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.08h， 生成 (R)-2-[(4aR,6R,7R,8R,8aS)-7-Acetylamino-6-(naphthalen-2-ylmethoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid
  参考文献：
  名称：

  Synthesis of hydrophobic derivatives of muramyldipeptides

  摘要：

  DOI：

  10.1007/bf02273926
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-萘基甲基 2-乙酰氨基-2-脱氧吡喃己糖苷
  参考文献：
  名称：

  Synthesis and glycan priming activity of acetylated disaccharides

  摘要：

  Five disaccharides related in structure to the glycans of vertebrate mucins have been chemically synthesized using orthogonal blocking, coupling and deblocking techniques. These include 2-naphthylmethyl 3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-beta -D-glucopyranoside (6), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O -acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O -acetyl-beta -D-galactopyranoside (14), 2-naphthylmethy12,3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside oside (20), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2-acetamido-4, 6-di-O -acetyl-2-deoxy-or-D-galactopyranoside (23) and 2-naphthylmethyl 2-acetamido-3,4, 6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside (27). These per-O-acetylated compounds were fed to U-937 cells to test their ability to prime oligosaccharide synthesis, inhibit glycoprotein biosynthesis and alter adhesion to E-selectin expressed on endothelial cells. The results show that 6, 14, and 20 served as substrates for oligosaccharide synthesis. The generation of glycoside-primed glycans altered the formation of glycoproteins on the cell surface and inhibited cell adhesion dependent on E-selectin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00200-7

文献信息

• Syntheses of fluorine-containing mucin core 2/core 6 structures using novel fluorinated glucosaminyl donors
  作者：Jun Xue、Vipin Kumar、Sirajud D. Khaja、E.V. Chandrasekaran、Robert D. Locke、Khushi L. Matta

  DOI：10.1016/j.tet.2009.07.089

  日期：2009.10

  trisaccharides modified at the C-3 or C-4 position of the pertinent glucosamine residue required for mechanistic study of glycosyltransferases and sulfotransferases involved in the biosynthesis of O-glycans are reported. Novel fluorinated glucosaminyl donors were synthesized from 2-naphthylmethyl β-d-N-acetylglucosamine (β-O-NAP-GlcNAc) via double inversion of the C-3 or C-4 configuration. A one-step β-alkylation

  报道了在O-聚糖的生物合成中涉及的糖基转移酶和磺基转移酶的机理研究所需的相关葡糖胺残基的C-3或C-4位修饰的氟化粘蛋白核心6二糖和核心2三糖的合成。通过C-3或C-4构型的两次转化，由2-萘甲基β- d - N-乙酰基葡糖胺（β- O -NAP-GlcNAc）合成了新型氟化的氨基葡萄糖基供体。首次报道了GlcNAc的一步一步β-烷基化反应，以高收率提供了β- O -NAP-GlcNAc，这是寡糖合成中基于NAP-糖苷的合成策略的基石。
• Thioglycosides Are Efficient Metabolic Decoys of Glycosylation that Reduce Selectin Dependent Leukocyte Adhesion
  作者：Shuen-Shiuan Wang、Xuefeng Gao、Virginia del Solar、Xinheng Yu、Aristotelis Antonopoulos、Alan E. Friedman、Eryn K. Matich、G. Ekin Atilla-Gokcumen、Mehrab Nasirikenari、Joseph T. Lau、Anne Dell、Stuart M. Haslam、Roger A. Laine、Khushi L. Matta、Sriram Neelamegham

  DOI：10.1016/j.chembiol.2018.09.012

  日期：2018.12

  Metabolic decoys are synthetic analogs of naturally occurring biosynthetic acceptors. These compounds divert cellular biosynthetic pathways by acting as artificial substrates that usurp the activity of natural enzymes. While O-linked glycosides are common, they are only partially effective even at millimolar concentrations. In contrast, we report that N-acetylglucosamine (GlcNAc) incorporated into various thioglycosides robustly truncate cell surface N- and O-linked glycan biosynthesis at 10-100 mu M concentrations. The > 10-fold greater inhibition is in part due to the resistance of thioglycosides to hydrolysis by intracellular hexosaminidases. The thioglycosides reduce beta-galactose incorporation into lactosamine chains, cell surface sialyl Lewis-X expression, and leukocyte rolling on selectin substrates including inflamed endothelial cells under fluid shear. Treatment of granulocytes with thioglycosides prior to infusion into mouse inhibited neutrophil homing to sites of acute inflammation and bone marrow by similar to 80%-90%. Overall, thioglycosides represent an easy to synthesize class of efficient metabolic inhibitors or decoys. They reduce N-/O-linked glycan biosynthesis and inflammatory leukocyte accumulation.
• Xue, Jun; Khaja, Sirajud D.; Locke, Robert D., Synlett, 2004, # 5, p. 861 - 865
  作者：Xue, Jun、Khaja, Sirajud D.、Locke, Robert D.、Matta, Khushi L.

  DOI：——

  日期：——
• Synthesis of hydrophobic derivatives of muramyldipeptides
  作者：A. E. Zemlyakov、V. O. Kur'yanov、V. V. Tsikalov、E. A. Aksenova、V. Ya. Chirva

  DOI：10.1007/bf02273926

  日期：1997.1
• Synthesis and glycan priming activity of acetylated disaccharides
  作者：Arun K Sarkar、Jillian R Brown、Jeffrey D Esko

  DOI：10.1016/s0008-6215(00)00200-7

  日期：2000.11

  Five disaccharides related in structure to the glycans of vertebrate mucins have been chemically synthesized using orthogonal blocking, coupling and deblocking techniques. These include 2-naphthylmethyl 3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-beta -D-glucopyranoside (6), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O -acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O -acetyl-beta -D-galactopyranoside (14), 2-naphthylmethy12,3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside oside (20), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2-acetamido-4, 6-di-O -acetyl-2-deoxy-or-D-galactopyranoside (23) and 2-naphthylmethyl 2-acetamido-3,4, 6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside (27). These per-O-acetylated compounds were fed to U-937 cells to test their ability to prime oligosaccharide synthesis, inhibit glycoprotein biosynthesis and alter adhesion to E-selectin expressed on endothelial cells. The results show that 6, 14, and 20 served as substrates for oligosaccharide synthesis. The generation of glycoside-primed glycans altered the formation of glycoproteins on the cell surface and inhibited cell adhesion dependent on E-selectin. (C) 2000 Elsevier Science Ltd. All rights reserved.