2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-1,3,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranose | 1499187-38-0

• 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)-1,3,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranose
• CAS: 1499187-38-0
• 化学式: C₂₆H₃₅N₃O₁₇
• 分子量: 661.574
• InChiKey: XNCHAEIOCATQMJ-IMGJLKSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.08
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  260.55
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-1,3,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以75%的产率得到β-D-glucopyranosyl-(1→4)-2-azido-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  Azido derivatives of cellobiose: oxidation at C1 with cellobiose dehydrogenase from Sclerotium rolfsii

  摘要：

  We report the chemo-enzymatic synthesis of three cellobiono-1,5-lactone azido derivatives, designed as building blocks for biomedical polymer scaffolds. The synthesis is based on regioselective protection of cellobiose or 1,6-O-anhydro-beta-D-cellobiose before azidation and subsequent deprotection. The oxidation to the corresponding cellobiono-1,5-lactones was investigated with 6'-azido-6'-deoxycellobiose (6'N(3)Clb, 5), 6-azido-6-deoxycellobiose (6N(3)Clb, 11) and 2-azido-2-deoxycellobiose (2N(3)Clb, 15) under the catalysis of cellobiose dehydrogenase (CDH) from the plant-pathogenic fungus Sclerotium rolfsii. Substrate binding characteristics and kinetics of CDH for the three cellobiose azido derivatives were studied employing computational docking, steady-state and presteady-state techniques. The process of enzymatic oxidation of the cellobiose azido intermediates was optimized by using the available kinetic information. Whereas the conversion of 15 by CDH is very slow, the conversion of 5 and 11 by a regenerated, bi-enzymatic process (CDH/redox mediator/laccase/O-2) is fast, quantitative and produces azido derivatives of cellobiono-1,5-lactone in an environmentally friendly, oxygen-driven process. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.09.004
• 作为产物：
  描述：

  六乙酰基-D-纤维二糖烯 在 sodium azide 、 ammonium cerium (IV) nitrate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-1,3,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  [EN] METHOD FOR SEPARATING CHROMATOGRAPHICALLY INDISTINGUISHABLE 2-AZIDO-1-NITRATES
  [FR] PROCÉDÉ DE SÉPARATION DE 2-AZIDO-1-NITRATES INDISTINGUABLES PAR CHROMATOGRAPHIE

  摘要：

  本发明公开了一种从色谱上无法区分的1,2-二轴向和1,2-二赤道二糖2-叠氮基-1-硝酸酯中分离1,2-二轴向的方法，其中二糖是1→4二糖，包括以下步骤：-提供一个混合物，其中色谱上无法区分的1,2-二轴向和1,2-二赤道2-叠氮基-1-硝酸酯，-用来自四烷基铵盐组的亲核试剂处理混合物，优选为四烷基铵硝酸盐，-从处理后的混合物中获取1-轴向-2-赤道2-叠氮基-1-硝酸酯。

  公开号：

  WO2019002594A1

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。