2,3,4-tri-O-benzoyl-5-thio-β-L-fucopyranosyl dibenzyl phosphate | 182694-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4-tri-O-benzoyl-5-thio-β-L-fucopyranosyl dibenzyl phosphate
• 英文别名: [(2S,3S,4R,5S,6S)-4,5-dibenzoyloxy-6-bis(phenylmethoxy)phosphoryloxy-2-methylthian-3-yl] benzoate
• CAS: 182694-24-2
• 化学式: C₄₁H₃₇O₁₀PS
• 分子量: 752.779
• InChiKey: XEMDDZQRNWVMED-IGUIPDPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  53
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-5-thio-β-L-fucopyranosyl dibenzyl phosphate 在 palladium on activated charcoal 氢气 、 三乙胺 、 吡啶 、 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 60.0h， 以98%的产率得到5-thio-β-L-fucopyranosyl phosphate diammonium 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-L-fucose 在 吡啶 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 2,3,4-tri-O-benzoyl-5-thio-β-L-fucopyranosyl dibenzyl phosphate
  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

• p-Nitrophenyl 1,5-dithio-α-l-fucopyranoside: a novel sulfur based fucosidase inhibitor
  作者：Osamu Tsuruta、Hideya Yuasa、Hironobu Hashimoto

  DOI：10.1016/0960-894x(96)00356-3

  日期：1996.8

  Five 5-thio-alpha-L-fucopyranosyl derivatives were prepared and examined as inhibitors of the alpha-L-fucosidase from bovine epididymis. The inhibitory activities of the fucosides strongly depend on the hydrophobicity of the aglycon. The best inhibition (K-i = 3.3 mu M) was obtained with p-nitrophenyl 1,5-dithio-alpha-L-fucopyranoside. Copyright (C) 1996 Elsevier Science Ltd.