ethyl 6-O-acetyl-2,3,5-tri-O-benzoyl-1-thio-β-D-galactofuranoside | 259826-52-3

• 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: ethyl 6-O-acetyl-2,3,5-tri-O-benzoyl-1-thio-β-D-galactofuranoside
• CAS: 259826-52-3
• 化学式: C₃₁H₃₀O₉S
• 分子量: 578.64
• InChiKey: BASKDWHDKABDEE-NRRUCQAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-acetyl-2,3,5-tri-O-benzoyl-1-thio-β-D-galactofuranoside 在 甲醇 、 三乙胺 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 ethyl 2,3,6-tri-O-benzoyl-1-thio-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：

  乙硫醇 、 6-O-acetyl-2,3,5-tri-O-benzoyl-α,β-D-galactofuranosyl acetate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以78%的产率得到ethyl 6-O-acetyl-2,3,5-tri-O-benzoyl-1-thio-β-D-galactofuranoside
  参考文献：
  名称：

  An Efficient Method for the Synthesis of A 1,6-Anhydro-α-D-Galactofuranose Derivative and its Application in the Synthesis of Oligosaccharides

  摘要：

  Synthesis of 1,6-anhydro-2,3,5-tri-O-benzoyl-beta-D-galactofuranose (3) has been achieved in good yield by stannic chloride catalysed ring closure of methyl 2,3,4-tri-O-benzoyl-6-O-benzyl-beta-D-galactofuranoside (1). The anhydro compound 3 was converted to the furanoside donors 6 and 7 with an easily removable O-6 acetyl group. The donors 6 and 7 were utilised for the synthesis of a di- and a trisaccharide containing beta-D-galactofuranosides.

  DOI：

  10.1080/07328309908544059

文献信息

• Sarkar, Sujit Kumar; Roy, Nirmolendu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 11, p. 2386 - 2394
  作者：Sarkar, Sujit Kumar、Roy, Nirmolendu

  DOI：——

  日期：——