2,4-di-O-acetyl-3-O-chloroacetyl-α-D-xylopyranosyl bromide | 92528-14-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,4-di-O-acetyl-3-O-chloroacetyl-α-D-xylopyranosyl bromide
• 英文别名: 2,4-di-O-acetyl-3-O-chloroacetyl-α-D-xylosyl bromide
• CAS: 92528-14-8
• 化学式: C₁₁H₁₄BrClO₇
• 分子量: 373.585
• InChiKey: ZIUARVVDNOAZKN-DQDDRIPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,4-di-O-acetyl-3-O-chloroacetyl-α-D-xylopyranosyl bromide 在 2,6-二甲基吡啶 、 calcium sulfate 、 silver carbonate 、 三氟化硼乙醚 、 乙酸肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.67h， 生成 (3R,4R)-4-benzoyloxy-1-benzyloxycarbonyl-3-[tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-β-D-xylopyranosyloxy]piperidine
  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
• 作为产物：
  描述：

  1,2,4-tri-O-acetyl-3-O-chloroacetyl-β-D-xylopyranose 在 氢溴酸 、 溶剂黄146 作用下， 生成 2,4-di-O-acetyl-3-O-chloroacetyl-α-D-xylopyranosyl bromide
  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

文献信息

• Synthesis of reducing disaccharides of d-xylopyranose
  作者：Gérard Excoffier、Didier Gagnaire、Jean-Pierre Utille

  DOI：10.1016/0008-6215(84)85331-8

  日期：1984.6

  Abstract Twenty-one derivatives of reducing disaccharides, d -xylopyranosyl-(1→2)-, -(1→3)-, and -(1→4)-α- or -β- d -xylose were synthesized according to the Helferich and Zirner method. Disaccharides having a pyranose reducing unit were prepared by condensation of 2,3,4-tri-O-acetyl-, 2,4-di-O-acetyl-3-O-chloroacetyl-, and 2,3-di-O-acetyl-4-O-chloroacetyl-α- d -xylopyranosyl bromide with tri-O-acetyl-β-

  摘要合成了二十一种还原二糖衍生物，d-吡喃吡喃糖基-（1→2）-，-（1→3）-和-（1→4）-α-或-β-d-木糖。 Helferich和Zirner方法。通过将2,3,4-三-O-乙酰基-，2,4-二-O-乙酰基-3-O-氯乙酰基和2,3-二-O-缩合来制备具有吡喃糖还原单元的二糖。乙酰基-4-O-氯乙酰基-α-d-吡喃木糖基溴化物与三-O-乙酰基-β-d-吡喃木糖衍生物; 其中1,2,4-三-O-乙酰基-3-O-（2,4-二-O-乙酰基-β-d-吡喃吡喃糖基）-β-d-木吡喃糖和1,2,3-三吡喃糖制备了在非还原糖基团中具有游离羟基的-O-乙酰基-4-O-（2,3-二-O-乙酰基-β-d-吡喃木糖基）-β-d-木吡喃糖，用于合成高级-分子量 线性低聚物。容易获得的5-O-氯乙酰基或5-O-乙酰基-1,2-O-异亚丙基-α-d-木呋喃糖的糖基化反应为1，2-O-异亚丙基-3-O-β-d