allyl 2,3,6-tri-O-benzoyl-β-D-galactofuranoside | 1236300-05-2

• 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: allyl 2,3,6-tri-O-benzoyl-β-D-galactofuranoside
• 英文别名: [(2R)-2-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-prop-2-enoxyoxolan-2-yl]-2-hydroxyethyl] benzoate
• CAS: 1236300-05-2
• 化学式: C₃₀H₂₈O₉
• 分子量: 532.547
• InChiKey: HNEOVZXYMORZRF-OFBRLNSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl 2,3,6-tri-O-benzoyl-β-D-galactofuranoside 在 四氢吡咯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以73%的产率得到allyl 2,3,5-tri-O-benzoyl-β-D-galactofuranoside
  参考文献：
  名称：

  使用吡喃糖苷到呋喃糖苷重排和受控的O（5）→O（6）苯甲酰迁移作为合成策略的基础，以组装（1→5）-和（1→6）-连接的半乳​​糖呋喃糖基链

  摘要：

  选择性保护的吡喃半乳糖苷的新吡喃糖苷-呋喃糖苷（PIF）重排，然后受控的O（5）→O（6）苯甲酸酯迁移，得到5-OH或6-OH产品。它已被用于从烟曲霉中合成与半乳甘露聚糖有关的四种寡糖。通过应用末端甘露糖苷和双半呋喃糖苷嵌段，在半乳糖呋喃糖基残基之间包含（1→5）和（1→6）连接的目标寡糖的组装，形成了一种针对包含5-O-和6的真菌和细菌碳水化合物抗原的通用方法-O-取代的半乳糖呋喃糖苷残基。

  DOI：

  10.1021/acs.orglett.6b02735
• 作为产物：
  描述：

  在 四氢吡咯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以88%的产率得到allyl 2,3,6-tri-O-benzoyl-β-D-galactofuranoside
  参考文献：
  名称：

  使用吡喃糖苷到呋喃糖苷重排和受控的O（5）→O（6）苯甲酰迁移作为合成策略的基础，以组装（1→5）-和（1→6）-连接的半乳​​糖呋喃糖基链

  摘要：

  选择性保护的吡喃半乳糖苷的新吡喃糖苷-呋喃糖苷（PIF）重排，然后受控的O（5）→O（6）苯甲酸酯迁移，得到5-OH或6-OH产品。它已被用于从烟曲霉中合成与半乳甘露聚糖有关的四种寡糖。通过应用末端甘露糖苷和双半呋喃糖苷嵌段，在半乳糖呋喃糖基残基之间包含（1→5）和（1→6）连接的目标寡糖的组装，形成了一种针对包含5-O-和6的真菌和细菌碳水化合物抗原的通用方法-O-取代的半乳糖呋喃糖苷残基。

  DOI：

  10.1021/acs.orglett.6b02735

文献信息

• Fidelity and Promiscuity of a Mycobacterial Glycosyltransferase
  作者：Kenzo Yamatsugu、Rebecca A. Splain、Laura L. Kiessling

  DOI：10.1021/jacs.6b04481

  日期：2016.7.27

  Members of the genus Mycobacterium cause devastating human diseases, including tuberculosis. Mycobacterium tuberculosis can resist some antibiotics because of its durable and impermeable cell envelope. This barrier is assembled from saccharide building blocks not found in mammals, including galactofuranose (Galf). Within the cell envelope, Galf residues are linked together to afford an essential polysaccharide, termed the galactan. The formation of this polymer is catalyzed by the glycosyltransferase GlfT2, a processive carbohydrate polymerase, which generates a sequence-specific polysaccharide with alternating regioisomeric beta(1-5) and beta(1-6) Galf linkages. GlfT2 exhibits high fidelity in linkage formation, as it will terminate polymerization rather than deviate from its linkage pattern. These findings suggest that GlfT2 would prefer an acceptor with a canonical alternating beta(1-5) and beta(1-6) Galf sequence. To test this hypothesis, we devised a synthetic route to assemble oligosaccharides with natural and non-natural sequences. GlfT2 could elongate each of these acceptors, even those with non-natural linkage patterns. These data indicate that the glycosyltransferase is surprisingly promiscuous in its substrate preferences. However, GlfT2 did favor some substrates: it preferentially acted on those in which the lipid-bearing Galf residue was connected to the sequence by a beta(1-6) glycosidic linkage. The finding that the relative positioning of the lipid and the non-reducing end of the acceptor influences substrate selectivity is consistent with a role for the lipid in acceptor binding. The data also suggest that the fidelity of GlfT2 for generating an alternating beta(1-5) and beta(1-6) pattern of Galf residues arises not from preferential substrate binding but during processive elongation. These observations suggest that inhibiting the action of GlfT2 will afford changes in cell wall structure.
• Synthesis of galactofuranose-based acceptor substrates for the study of the carbohydrate polymerase GlfT2
  作者：Rebecca A. Splain、Laura L. Kiessling

  DOI：10.1016/j.bmc.2010.04.068

  日期：2010.6.1

  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.