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 | 36954-64-0

• 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-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose
• 英文别名: O-(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；O-(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；Glc2Ac3Ac4Ac6Ac(b1-4)a-GlcNAc1Ac3Ac6Ac；[(2R,3S,4R,5R,6R)-5-acetamido-4,6-diacetyloxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 36954-64-0
• 化学式: C₂₈H₃₉NO₁₈
• 分子量: 677.614
• InChiKey: XKTWMUHXXMTTHP-RSIYDKPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  241
• 氢给体数：
  1
• 氢受体数：
  18

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-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸酐 、 三氟甲磺酸三甲基硅酯 、 camphor-10-sulfonic acid 、 三乙基硅基三氟甲磺酸酯 、 sodium methylate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 aq. phosphate buffer 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 46.5h， 生成
  参考文献：
  名称：

  GLYCOPROTEIN SYNTHESIS AND REMODELING BY ENZYMATIC TRANSGLYCOSYLATION

  摘要：

  公开号：

  EP2001358B1
• 作为产物：
  描述：

  Benzyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-alpha-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 、 silver trifluoromethanesulfonate 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 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

文献信息

• Glycopeptide Synthesis throughendo-Glycosidase-Catalyzed Oligosaccharide Transfer of Sugar Oxazolines: Probing Substrate Structural Requirement
  作者：Ying Zeng、Jingsong Wang、Bing Li、Steven Hauser、Hengguang Li、Lai-Xi Wang

  DOI：10.1002/chem.200501196

  日期：2006.4.12

  An array of sugar oxazolines was synthesized and tested as donor substrates for the Arthrobacter endo-beta-N-acetylglucosaminidase (Endo-A)-catalyzed glycopeptide synthesis. The experiments revealed that the minimum structure of the donor substrate required for Endo-A catalyzed transglycosylation is a Man beta1-->4-GlcNAc oxazoline moiety. Replacement of the beta-D-Man moiety with beta-D-Glc, beta-D-Gal

  合成了一系列糖恶唑啉，并测试了它们作为节杆菌内-β-N-乙酰氨基葡糖苷酶（Endo-A）催化的糖肽合成的供体底物。实验表明，Endo-A催化转糖基化所需的供体底物的最小结构是Man beta1-> 4-GlcNAc恶唑啉部分。用β-D-Glc，β-D-Gal和β-D-GlcNAc单糖替代β-D-Man部分会导致二糖恶唑啉的底物活性降低。尽管如此，该酶仍可耐受修饰，例如在β-D-Man部分的3和/或6位上附加糖残基或官能团的连接，从而使选择性修饰的寡糖成功转移到肽上受体。另一方面，该酶在受体部分具有很大的柔韧性，可以同时使用大大小小的GlcNAc肽作为受体。研究表明，内切糖苷酶催化的转糖基化在构建天然和选择性修饰糖肽方面都具有巨大潜力。