12-phenoxy-dodec-2-enyl β-D-galactofuranoside | 1236300-02-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 12-phenoxy-dodec-2-enyl β-D-galactofuranoside
• CAS: 1236300-02-9
• 化学式: C₂₄H₃₈O₇
• 分子量: 438.562
• InChiKey: WYEQARZHEJCTLM-ZSXJVMONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  31.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  108.61
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  12-phenoxy-dodec-2-enyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranoside 在 甲醇 、 sodium methylate 作用下， 反应 3.0h， 以75%的产率得到12-phenoxy-dodec-2-enyl β-D-galactofuranoside
  参考文献：
  名称：

  Synthesis of galactofuranose-based acceptor substrates for the study of the carbohydrate polymerase GlfT2

  摘要：

  Despite the prevalence and importance of carbohydrate polymers, the molecular details of their biosynthesis remain elusive. Many enzymes responsible for the synthesis of carbohydrate polymers require a 'primer' or 'initiator' carbohydrate sequence. One example of such an enzyme is the mycobacterial galactofuranosyltransferase GlfT2 (Rv3808c), which generates an essential cell wall building block. We recently demonstrated that recombinant GlfT2 is capable of producing a polymer composed of alternating beta-(1,5) and beta-(1,6)-linked galactofuranose (Galf) residues. Intriguingly, the length of the polymers produced from a synthetic glycosyl acceptor is consistent with those found in the cell wall. To probe the mechanism by which polymer length is controlled, a collection of initiator substrates has been assembled. The central feature of the synthetic route is a ruthenium-catalyzed cross-metathesis as the penultimate transformation. Access to synthetic substrates has led us to postulate a new mechanism for length control in this template-independent polymerization. Moreover, our investigations indicate that lipids possessing but a single galactofuranose residue can act as substrates for GlfT2. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.068