2,3,4,6-tetra-O-acetyl-5-thio-D-mannopyranosyl bromide | 223267-02-5

• 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: 2,3,4,6-tetra-O-acetyl-5-thio-D-mannopyranosyl bromide
• 英文别名: [(2R,3S,4S,5S,6R)-3,4,5-triacetyloxy-6-bromothian-2-yl]methyl acetate
• CAS: 223267-02-5
• 化学式: C₁₄H₁₉BrO₈S
• 分子量: 427.27
• InChiKey: BTYFSHURCAIDLA-DGTMBMJNSA-N

物化性质

• 沸点：
  430.2±45.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-5-thio-D-mannopyranosyl bromide 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 苯 为溶剂， 反应 49.0h， 生成 5-thio-α-D-mannopyranosyl phosphate tributylammonium salt
  参考文献：
  名称：

  Synthesis of GDP-5-thiosugars and Their Use as Glycosyl Donor Substrates for Glycosyltransferases

  摘要：

  Two thiopyranoside analogues of GDP-sugars, GDP-5-thio-D-mannose (14) and GDP-5-thio-L-fucose (15), were synthesized. The syntheses included the phosphorylations of tetra-O-acetyl-5-thio-D-mannosyl bromide (4) and tri-O-benzoyl-L-fucosyl bromide (6) with silver dibenzyl phosphate, deprotection of the phosphate groups, and condensation of the deprotected phosphates with GMP-imidazolidate (13) in the presence of MgCl2. These GDP-sugar analogues were found to be donor substrates for alpha(1,2)mannosyltransferase and alpha(1,3)fucosyltransferase, affording a 5-thiomannose-containing disaccharide (18) and a 5-thiofucose-containing trisaccharide (21), respectively. The conformation of the disaccharide analogue 18 was similar to that of its native counterpart by ROESY. These findings for GDP-5-thiosugars together with previous demonstrations of enzymatic transfer from UDP-5-thiosugars will allow the production of panels of oligosaccharide analogues with hydrolase-resistant properties.

  DOI：

  10.1021/jo0300035
• 作为产物：
  描述：

  5-thio-D-mannopyranose penta-acetate 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,3,4,6-tetra-O-acetyl-5-thio-D-mannopyranosyl bromide
  参考文献：
  名称：

  Synthesis of GDP-5-thiosugars and Their Use as Glycosyl Donor Substrates for Glycosyltransferases

  摘要：

  Two thiopyranoside analogues of GDP-sugars, GDP-5-thio-D-mannose (14) and GDP-5-thio-L-fucose (15), were synthesized. The syntheses included the phosphorylations of tetra-O-acetyl-5-thio-D-mannosyl bromide (4) and tri-O-benzoyl-L-fucosyl bromide (6) with silver dibenzyl phosphate, deprotection of the phosphate groups, and condensation of the deprotected phosphates with GMP-imidazolidate (13) in the presence of MgCl2. These GDP-sugar analogues were found to be donor substrates for alpha(1,2)mannosyltransferase and alpha(1,3)fucosyltransferase, affording a 5-thiomannose-containing disaccharide (18) and a 5-thiofucose-containing trisaccharide (21), respectively. The conformation of the disaccharide analogue 18 was similar to that of its native counterpart by ROESY. These findings for GDP-5-thiosugars together with previous demonstrations of enzymatic transfer from UDP-5-thiosugars will allow the production of panels of oligosaccharide analogues with hydrolase-resistant properties.

  DOI：

  10.1021/jo0300035

文献信息

• Syntheses of two trimannose analogs each containing C-mannosyl or 5-thio-C-mannosyl residue: their affinities to concanavalin A
  作者：Osamu Tsuruta、Hideya Yuasa、Sadamu Kurono、Hironobu Hashimoto

  DOI：10.1016/s0960-894x(99)00087-6

  日期：1999.3

  C-Mannosyl residue-containing trimannose ManC alpha(1,6)Man alpha(1,3)Man} (2) and 5-thio-C-mannosyl residue-containing trimannose 5SManC alpha(1,6)Man alpha(1,3)Man} (3) were synthesized via a glycosyl radical addition to enone derivative of mannose (6). Dissociation constants for the binding of these trisaccharides to concanavalin A (ConA) were determined by a fluorescence anisotropy inhibition assay: K-d = 198 and 31 mu M, respectively. The unexpectedly large K-d value for the compound 2 compared with the compound 3 and the natural trimannose 1 demonstrates a characteristic of C-glycoside. (C) 1999 Elsevier Science Ltd. All rights reserved.