phenyl β-D-xylopyranosyl(1->3)-1-thio-β-D-xylopyranoside | 1363568-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl β-D-xylopyranosyl(1->3)-1-thio-β-D-xylopyranoside
• CAS: 1363568-08-4
• 化学式: C₁₆H₂₂O₈S
• 分子量: 374.412
• InChiKey: XUXGFOKHECTEAO-UTDAFUOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.32
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  128.84
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  phenyl tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-1-thio-β-D-xyloside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以89%的产率得到phenyl β-D-xylopyranosyl(1->3)-1-thio-β-D-xylopyranoside
  参考文献：
  名称：

  Mechanistic Insights into the 1,3-Xylanases: Useful Enzymes for Manipulation of Algal Biomass

  摘要：

  Xylanases capable of degrading the crystalline microfibrils of 1,3-xylan that reinforce the cell walls of some red and siphonous green algae have not been well studied, yet they could prove to be of great utility in algaculture for the production of food and renewable chemical feedstocks. To gain a better mechanistic understanding of these enzymes, a suite of reagents was synthesized and evaluated as substrates and inhibitors of an endo-1,3-xylanase. With these reagents, a retaining mechanism was confirmed for the xylanase, its catalytic nucleophile identified, and the existence of -3 to +2 substratebinding subsites demonstrated. Protein crystal X-ray diffraction methods provided a high resolution structure of a trapped covalent glycosyl enzyme intermediate, indicating that the 1,3-xylanases likely utilize the S-1(3)-> H-4(3)-> C-4(1) conformational itinerary to effect catalysis.

  DOI：

  10.1021/ja211836t