GlcNAc(b1-4)a-Glc2F

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: GlcNAc(b1-4)a-Glc2F
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6S)-5-fluoro-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₁₄H₂₄FNO₁₀
• 分子量: 385.344
• InChiKey: FOEMYTLALDIRRS-SGZQVOMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  178
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 GlcNAc(b1-4)a-Glc2F 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 3.0h， 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-fluoro-β-D-glucopyranose 、 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-1,3,6-tri-O-acetyl-2-deoxy-2-fluoro-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：

  2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 在 palladium on activated charcoal 、 镍 4 A molecular sieve 、 三氟化硼乙醚 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 GlcNAc(b1-4)a-Glc2F
  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

文献信息

• 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.