β-D-ribopyranosyl urea | 20240-01-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-ribopyranosyl urea
• 英文别名: ribofuranosylurea；β-D-Ribopyranosyl-harnstoff；[(2R,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]urea
• CAS: 20240-01-1
• 化学式: C₆H₁₂N₂O₅
• 分子量: 192.172
• InChiKey: BGTOCAYOOXODIK-TXICZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  D-核糖 、 尿素 在 盐酸 作用下， 生成 α-D-ribopyranosyl urea 、 β-D-ribopyranosyl urea
  参考文献：
  名称：

  761.糖基脲。第一部分D-葡糖基脲和D-核糖基脲的制备和一些反应

  摘要：

  DOI：

  10.1039/jr9600003837

文献信息

• Naito; Kawakami, Chemical and pharmaceutical bulletin, 1962, vol. 10, p. 627,631
  作者：Naito、Kawakami

  DOI：——

  日期：——
• Ribosylurea Accumulates in Yeast<i>urc4</i>Mutants
  作者：O. Björnberg、M. Vodnala、V. Domkin、A. Hofer、A. Rasmussen、G. Andersen、J. Piškur

  DOI：10.1080/15257771003741265

  日期：2010.6.10

  Yeast Saccharomyces (Lachancea) kluyveri urc4 mutants, unable to grow on uracil, biotransformed 14C2-uracil into two labeled compounds, as detected by high performance liquid chromatography (HPLC). These two compounds could also be obtained following organic synthesis of ribosylurea. This finding demonstrates that in the URC pyrimidine degradation pathway, the opening of the uracil ring takes place when uracil is attached to the ribose moiety. Ribosylurea has not been reported in the cell metabolism before and the two observed compounds likely represent an equilibrium mixture of the pyranosyl and furanosyl forms.
• Direct formation and isolation of unprotected α-and β-d-ribopyranosyl urea, α-and β-d-ribofuranosyl urea, and a ribosyl-1,2-cyclic carbamate in carbohydrate melts
  作者：Norman W.H. Cheetham、Trong D. Tran

  DOI：10.1016/j.carres.2020.108021

  日期：2020.6

  Solvent-free melts of unprotected D-ribose and urea generated mainly C-1-substituted ribosyl products. The remarkable resolving power of a graphitised-carbon HPLC column allowed products of the reaction formed over a range of heating times and temperatures to be monitored. Heating an uncatalysed mixture of D-ribose and urea at temperatures between 75 degrees C and 90 degrees C resulted in complex mixtures of compounds; after 19 h heating at 90 degrees C, up to ten components could be resolved. At shorter heating times and lower temperatures, the composition and distribution of products varied. By manipulation of the reaction time and temperature, and with the addition of an acid catalyst, it was possible to optimise the yields of selected products. Thus, the acid-catalysed reaction after 1-2 h at 80 degrees C gave optimal yields of alpha- and beta-D-ribopyranosyl urea, whereas the uncatalysed reaction after 22 h at 75-78 degrees C in addition produced significant amounts of alpha-D-ribofuranosyl-1,2-cyclic carbamate [glyco-1,2-oxazolidin-2-one] plus the alpha- and beta-ribofuranosyl ureas. The five compounds were isolated and characterised, demonstrating the significant advantages of this approach; its simplicity, and the ability to produce multiple compounds of biological interest in a single step. LC/MS was used to identify tentatively several other components of the reaction mixture. The unprotected title compounds were prepared, isolated and characterised with water as the only solvent.