2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-trifluoromethyl-(2-acetamido-3,6-di-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline | 370859-42-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-trifluoromethyl-(2-acetamido-3,6-di-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline
• 英文别名: (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-trifluoromethyl-(3,6-di-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1,d]-2-oxazoline；[(3aR,5R,6S,7R,7aR)-6-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-7-acetyloxy-2-(trifluoromethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazol-5-yl]methyl acetate
• CAS: 370859-42-0
• 化学式: C₂₆H₃₃F₃N₂O₁₅
• 分子量: 670.548
• InChiKey: WSRVDUXUKMRXJP-UJXHPAMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  210
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-trifluoromethyl-(2-acetamido-3,6-di-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranosyl phosphate
  参考文献：
  名称：

  Substrate Specificity of the Glycosyl Donor for Oligosaccharyl Transferase

  摘要：

  Oligosaccharyl transferase (OT) catalyzes the co-translational transfer of a dolichol-linked tetradecasaccharide (Dol-PP-GlcNAc(2)Man(9)Glc(3),1a) to an asparagine side chain of a nascent polypeptide inside the lumen of the endoplasmic reticulum. (ER). The glycosyl acceptor requires an Asn-Xaa-Thr/Ser sequon, where Xaa can be any natural amino acid except proline, for N-linked glycosylation to occur. To address the substrate specificity of the glycosyl donor, three unnatural dolichol-linked disaccharide analogues (Dol-PP-GlcNTFA-GlcNAc 1c, Dol-PP-2DFGlc-GlcNAc Id, and Dol-PP-GlcNAc-Glc le) were synthesized and evaluated as substrates or inhibitors for OT from yeast. The synthetic analogue Dol-PP-GlcNAc-Glc le, with substitution in the distal sugar, was found to be a substrate (K-mapp = 26 muM for OT. On the other hand, the analogues Dol-PP-GlcNTFA-GlcNAc le (Ki = 154 muM) and Dol-PP-2DFGlc-GlcNAc 1d (K-i = 25 muM), with variations in the proximal sugar, were inhibitors for OT. The dolichol-linked monosaccharide Dol-PP-GlcNAc 3 was found to be the minimum unit for glycosylation to occur.

  DOI：

  10.1021/jo0100345
• 作为产物：
  描述：

  2-(乙酰氨基)-2-脱氧-4-O-[3,4,6-三-O-乙酰基-2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡萄糖基]-alpha-D-吡喃葡萄糖 1,3,6-三乙酸酯 在 乙酸肼 、 甲基磺酸酐 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.17h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-trifluoromethyl-(2-acetamido-3,6-di-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline
  参考文献：
  名称：

  从几丁质到具有生物活性的壳寡糖及其结合物：获得脂寡糖和TMG-壳三霉素的途径

  摘要：

  容易从几丁质中获得的过乙酰化壳寡糖（COSs）的直接和化学选择性N-酰基化，生成过N-三氟乙酰基衍生物，为规模确定的COS和衍生的糖缀合物提供了诱人的途径。它涉及使用各种受体构件和三氟甲基恶唑啉二聚体供体，这些供体在1,2-反式糖基化反应中高效且具有高反应性。该方法用于制备对植物具有高活性的重要共生糖脂，以及用于昆虫，真菌和细菌N-乙酰氨基葡萄糖苷酶的强效特异性抑制剂TMG-chichitriomycin 。

  DOI：

  10.1002/anie.201406802

文献信息

• From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG-chitotriomycin
  作者：Guillaume Despras、Aurélien Alix、Dominique Urban、Boris Vauzeilles、Jean-Marie Beau

  DOI：10.1002/anie.201406802

  日期：2014.10.27

  The direct and chemoselective N‐transacylation of peracetylated chitooligosaccharides (COSs), readily obtained from chitin, to give per‐N‐trifluoroacetyl derivatives offers an attractive route to size‐defined COSs and derived glycoconjugates. It involves the use of various acceptor building blocks and trifluoromethyl oxazoline dimer donors prepared with efficiency and highly reactive in 1,2‐trans glycosylation

  容易从几丁质中获得的过乙酰化壳寡糖（COSs）的直接和化学选择性N-酰基化，生成过N-三氟乙酰基衍生物，为规模确定的COS和衍生的糖缀合物提供了诱人的途径。它涉及使用各种受体构件和三氟甲基恶唑啉二聚体供体，这些供体在1,2-反式糖基化反应中高效且具有高反应性。该方法用于制备对植物具有高活性的重要共生糖脂，以及用于昆虫，真菌和细菌N-乙酰氨基葡萄糖苷酶的强效特异性抑制剂TMG-chichitriomycin 。
• Substrate Specificity of the Glycosyl Donor for Oligosaccharyl Transferase
  作者：Vincent W.-F. Tai、Barbara Imperiali

  DOI：10.1021/jo0100345

  日期：2001.9.1

  Oligosaccharyl transferase (OT) catalyzes the co-translational transfer of a dolichol-linked tetradecasaccharide (Dol-PP-GlcNAc(2)Man(9)Glc(3),1a) to an asparagine side chain of a nascent polypeptide inside the lumen of the endoplasmic reticulum. (ER). The glycosyl acceptor requires an Asn-Xaa-Thr/Ser sequon, where Xaa can be any natural amino acid except proline, for N-linked glycosylation to occur. To address the substrate specificity of the glycosyl donor, three unnatural dolichol-linked disaccharide analogues (Dol-PP-GlcNTFA-GlcNAc 1c, Dol-PP-2DFGlc-GlcNAc Id, and Dol-PP-GlcNAc-Glc le) were synthesized and evaluated as substrates or inhibitors for OT from yeast. The synthetic analogue Dol-PP-GlcNAc-Glc le, with substitution in the distal sugar, was found to be a substrate (K-mapp = 26 muM for OT. On the other hand, the analogues Dol-PP-GlcNTFA-GlcNAc le (Ki = 154 muM) and Dol-PP-2DFGlc-GlcNAc 1d (K-i = 25 muM), with variations in the proximal sugar, were inhibitors for OT. The dolichol-linked monosaccharide Dol-PP-GlcNAc 3 was found to be the minimum unit for glycosylation to occur.