2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-acetyl-1,6-di-O-benzyl-2-deoxy-α-D-glucopyranose | 213738-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-acetyl-1,6-di-O-benzyl-2-deoxy-α-D-glucopyranose
• 英文别名: Glc2Ac3Ac4Ac6Ac(b1-4)[Bn(-6)]GlcNAc3Ac(a)-O-Bn；[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-6-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 213738-28-4
• 化学式: C₃₈H₄₇NO₁₆
• 分子量: 773.788
• InChiKey: XHBGVBZJIRKRDD-TYJMBCDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  55
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  207
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-acetyl-1,6-di-O-benzyl-2-deoxy-α-D-glucopyranose 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 生成 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-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
• 作为产物：
  描述：

  Benzyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-alpha-D-glucopyranoside 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以84%的产率得到2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2-acetamido-3-O-acetyl-1,6-di-O-benzyl-2-deoxy-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