allyl 2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranoside | 845532-35-6

• 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 2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranoside
• 英文别名: allyl 2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1,6)-2,3,5-tri-O-benzoyl-β-D-galactofuranoside；Bz(-2)[Bz(-3)][Bz(-5)]Galf(b1-6)[Bz(-2)][Bz(-3)][Bz(-5)]Galf(b)-O-allyl；[(2S,3S,4R,5R)-4-benzoyloxy-5-[(2R)-2-benzoyloxy-2-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-prop-2-enoxyoxolan-2-yl]ethoxy]-2-[(1R)-1-benzoyloxy-2-hydroxyethyl]oxolan-3-yl] benzoate
• CAS: 845532-35-6
• 化学式: C₅₇H₅₀O₁₇
• 分子量: 1007.01
• InChiKey: BACAJCCOSNHBIS-GLDYFQBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  74
• 可旋转键数：
  27
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  215
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  allyl 2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranoside 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到allyl 2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1,6)-2,3,6-tri-O-benzoyl-β-D-galactofuranoside
  参考文献：
  名称：

  Fidelity and Promiscuity of a Mycobacterial Glycosyltransferase

  摘要：

  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.

  DOI：

  10.1021/jacs.6b04481
• 作为产物：
  描述：

  allyl 6-O-acetyl-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranoside 在 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到allyl 2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzoyl-β-D-galactofuranoside
  参考文献：
  名称：

  β-（1→6）连接的d-半乳糖呋喃糖基六糖的高效简捷合成

  摘要：

  通过使用6-O-乙酰基-2,3,5-三-O-苯甲酰基的众所周知的施密特糖基化方法，以嵌段结构的方式有效地合成β-（1→6）-连接的D-半呋喃呋喃糖基六糖。 -β-D-半呋喃糖基三氯乙酰亚氨酸盐（1）和烯丙基2,3,5-三-O-苯甲酰基-β-D-半乳糖醛酸呋喃糖苷（3）为关键合成子。3与1的偶联得到β-（1-> 6）-连接的二糖4。随后4的选择性脱乙酰化得到二糖受体5，而4的去甲酰化反应随后形成三氯乙酰亚氨酸生成了二糖供体6。5与6的缩合。得到四糖7，随后脱乙酰基得到四糖受体8。最后，将8与6偶联，然后进行脱酰基，得到目标β-（1→6）连接的半乳​​糖呋喃糖六糖10。

  DOI：

  10.1016/j.carres.2004.11.001