thiazolin-2-yl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside | 514847-43-9

• 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: thiazolin-2-yl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside
• 英文别名: thiazolinyl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside；[(2R)-2-acetyloxy-2-[(2S,3S,4R,5S)-3,4-diacetyloxy-5-(4,5-dihydro-1,3-thiazol-2-ylsulfanyl)oxolan-2-yl]ethyl] acetate
• CAS: 514847-43-9
• 化学式: C₁₇H₂₃NO₉S₂
• 分子量: 449.503
• InChiKey: FKZDYVIQJAYIHJ-CWVYHPPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  177
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  thiazolin-2-yl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside 在 甲醇 、 sodium methylate 作用下， 以80%的产率得到(2S,3R,4R,5S)-2-(4,5-Dihydro-thiazol-2-ylsulfanyl)-5-((R)-1,2-dihydroxy-ethyl)-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  A novel synthesis of d-galactofuranosyl, d-glucofuranosyl and d-mannofuranosyl 1-phosphates based on remote activation of new and free hexofuranosyl donors

  摘要：

  The selective synthesis of 1,2-cis-hexofuranosyl 1-phosphates was readily accomplished according to a procedure based on the 'Remote Activation Concept'. This approach required (i) the preparation of suitable 1,2-trans-hexofuranosyl donors, so that new heterocyclic thiofuranosides were designed and synthesized, (ii) the stereocontrolled phosphorylation of the corresponding unprotected donors and (iii) the simple and fast purification of the resulting anomeric phosphates. This approach showed to be equally efficient in the galactose, glucose and mannose series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00822-3
• 作为产物：
  描述：

  2-巯基噻唑啉 、 1,2,3,5,6-penta-O-acetyl-β-D-galactofuranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到thiazolin-2-yl 2,3,5,6-tetra-O-acetyl-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

文献信息

• Synthesis of galactofuranose-containing disaccharides using thioimidoyl-type donors
  作者：Ronan Euzen、Vincent Ferrières、Daniel Plusquellec

  DOI：10.1016/j.carres.2006.10.001

  日期：2006.12

  Four galactofuranose-containing disaccharides have been prepared utilising various thioimidates [Galf-SC(=NR)XR'] and suitably protected acceptors as key precursors. We observed that the efficiency of the coupling reactions was particularly dependent on the aglycon present on the furanosyl donor when copper(II) ions were used as the promoter, and that activation could be correlated with the nature of the third heteroatorn, X. (c) 2006 Elsevier Ltd. All rights reserved.