2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-1,3,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranose | 370859-41-9

• 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)-1,3,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranose
• 英文别名: (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-1,3,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranose；GlcNAc3Ac4Ac6Ac(b1-4)[TfaNH(-2d)]a-Glc1Ac3Ac6Ac；[(2R,3S,4R,5R,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4,6-diacetyloxy-5-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 370859-41-9
• 化学式: C₂₈H₃₇F₃N₂O₁₇
• 分子量: 730.6
• InChiKey: RPHFTRAUCDYKTQ-JWVYPJMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  50
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  244
• 氢给体数：
  2
• 氢受体数：
  20

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)-1,3,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranose 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 生成
  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
• 作为产物：
  描述：

  2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride 在 吡啶 、 水 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-1,3,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranose
  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