1-allyl-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1,6)-2,3,5,6-tetra-O-acetyl-β-D-galactofuranoside | 1189533-96-7

• 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: 1-allyl-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1,6)-2,3,5,6-tetra-O-acetyl-β-D-galactofuranoside
• CAS: 1189533-96-7
• 化学式: C₄₄H₄₆O₁₈
• 分子量: 862.838
• InChiKey: YBTRJNJKXJPVJY-KJYSESJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  62.0
• 可旋转键数：
  19.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  1-allyl-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1,6)-2,3,5,6-tetra-O-acetyl-β-D-galactofuranoside 在 Grubbs catalyst first generation 、 甲醇 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 sodium iodide 作用下， 以 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 12-aminododecyl β-D-galactofuranosyl-(1,6)-β-D-galactofuranoside
  参考文献：
  名称：

  MICROBIAL GLYCANS AS A TARGET OF HUMAN INTELECTIN

  摘要：

  本公开提供了一种诊断和治疗细菌感染的方法。已经证明人类Intelectin 1（hIntL-1）选择性地结合细菌的糖基组分，包括肺炎链球菌、奇异变形杆菌、普通变形杆菌、肺炎克雷伯菌和鼠疫耶尔森氏菌。这种相互作用可以被用来识别、纯化和治疗这些细菌。

  公开号：

  US20160131649A1
• 作为产物：
  描述：

  allyl 2,3,5-tri-O-benzoyl-β-D-galactofuranoside 、 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到1-allyl-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1,6)-2,3,5,6-tetra-O-acetyl-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