dibenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl phosphate | 370859-50-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dibenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl phosphate
• 英文别名: [(2R,3R,4S,5R,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4-acetyloxy-6-bis(phenylmethoxy)phosphoryloxy-5-fluorooxan-2-yl]methyl acetate
• CAS: 370859-50-0
• 化学式: C₃₈H₄₇FNO₁₈P
• 分子量: 855.759
• InChiKey: PYINUXRLWHQGJR-IUHBSQDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  59
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  233
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  dibenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl phosphate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-fluoro-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-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-1,3,6-tri-O-acetyl-2-deoxy-2-fluoro-D-glucopyranose 在 氢溴酸 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 dibenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-fluoro-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