1-(tri-O-benzoyl-β-D-ribofuranosyl)-[1,3,5]triazinane-2,4,6-trione | 22432-99-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 1-(tri-O-benzoyl-β-D-ribofuranosyl)-[1,3,5]triazinane-2,4,6-trione
• 英文别名: 2′,3′,5′-O-tribenzoyl-1-(β-D-ribofuranosyl)cyanuric acid；1-(tri-O-benzoyl-β-D-ribofuranosyl)-[1,3,5]triazinane-2,4,6-trione
• CAS: 22432-99-1
• 化学式: C₂₉H₂₃N₃O₁₀
• 分子量: 573.516
• InChiKey: JBVGINYRBJVXQR-SSGKUCQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  175.85
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-(tri-O-benzoyl-β-D-ribofuranosyl)-[1,3,5]triazinane-2,4,6-trione 在 氨 、 三氯氧磷 作用下， 以 甲醇 、 水 、 叔丁醇 为溶剂， 反应 110.5h， 生成 Morpholin-4-yl-phosphonic acid mono-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2,4,6-trioxo-[1,3,5]triazinan-1-yl)-tetrahydro-furan-2-ylmethyl] ester; compound with N,N'-dicyclohexyl-morpholine-4-carboxamidine
  参考文献：
  名称：

  Synthesis of unnatural sugar nucleotides and their evaluation as donor substrates in glycosyltransferase-catalyzed reactions

  摘要：

  New unnatural sugar nucleotides, UDP-Fuc and CDP-Fuc were synthesized from fucose-beta-1-phosphate and nucleotide monophosphates activated as morpholidates. Furthermore, a nucleotide analogue was prepared by phosphorylation of 1-(beta-D-ribofuranosyl)cyan uric acid, itself obtained as a protected derivative by condensation of the persilylated derivative of cyanuric acid with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose in 74% yield. This phosphate activated according to the same procedure was condensed with fucose-beta-1-phosphate, affording a new sugar nucleotide conjugate (NDP-Fuc) which was evaluated together with UDP-Fuc, CDP-Fuc and ADP-Fuc, as facose donors in alpha-(1-->4/3)-fucosyltransferase (FucT-III) catalyzed reaction. Fucose transfer could be observed with each of the donors and kinetic parameters were determined using a fluorescent acceptor substrate. Efficiency of the four analogues towards FucT-III was in the following order: UDP-Fuc = ADP-Fuc > NDP-Fuc > CDP-Fuc.According to the same strategy ADP-GlcNAc was prepared from AMP-morpholidate and N-acetylglucosamine-alpha-1-phosphate; tested as a glucosaminyl donor towards Neisseria meningitidis N-acetylglucosaminyl transferase (LgtA), ADP-GlcNAc was recognized with 0.1% efficiency as compared with UDP-GlcNAc, the natural donor substrate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.09.002
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 tris(trimethylsilyl)cyanurate 在 四氯化钛 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以91%的产率得到1-(tri-O-benzoyl-β-D-ribofuranosyl)-[1,3,5]triazinane-2,4,6-trione
  参考文献：
  名称：

  氰基酸在RNA和核糖中的意外碱基配对行为与氰基酸诱导的核酸螺旋烯组装的关系：对Pre-RNA范例的启示

  摘要：

  氰尿酸（CA）杂环与腺嘌呤的核碱基/核苷和寡核苷酸形成超分子结构，导致人们猜测它们可以充当RNA的先行者。在本文中，研究了含有CA和CA-核糖核苷的RNA的组装行为。与以前的报道相反，RNA中的CA和CA-核糖核苷导致超分子组装的不稳定，从而导致CA-腺嘌呤六聚体花环结构的重新评估。提出了前所未有的非共价超分子螺旋结构，以解释行为上的显着差异，这对重组核酸结构的新范式，长螺旋的合成以及RNA前世界范式具有重要意义。

  DOI：

  10.1002/chem.202004397