α-D-ribopyranose | 7296-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-ribopyranose
• 英文别名: D-ribose；α-D-ribose；alpha-D-ribopyranose；(2S,3R,4R,5R)-oxane-2,3,4,5-tetrol
• CAS: 7296-59-5
• 化学式: C₅H₁₀O₅
• mdl: MFCD30479488
• 分子量: 150.131
• InChiKey: SRBFZHDQGSBBOR-AIHAYLRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-D-ribopyranose 在 吡啶 、 4-二甲氨基吡啶 、 高氯酸 、 水 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 2,3,4-Tri-O-acetyl-α-D-ribopyranose
  参考文献：
  名称：

  [EN] ACYLATED ACTIVE AGENTS AND METHODS OF THEIR USE FOR THE TREATMENT OF AUTOIMMUNE DISORDERS
  [FR] AGENTS ACTIFS ACYLÉS ET LEURS PROCÉDÉS D'UTILISATION POUR LE TRAITEMENT DE TROUBLES AUTO-IMMUNS

  摘要：

  公开号：

  WO2019236772A8
• 作为产物：
  描述：

  Ribopyranose 2,4-diphosphate 生成 α-D-ribopyranose
  参考文献：
  名称：

  MULLER, DANIEL;PITSCH, STEFAN;KITTAKA, ATSUSHI;WAGNER, ERNST;WINTNER, CAL+, HELV. CHIM. ACTA , 73,(1990) N, C. 1410-1468

  摘要：

  DOI：

文献信息

• Quantitative analysis of selective glycosylation of saccharides with aromatic amines
  作者：Toshihiko Hanai、Keiko Shimada、Nobuhiro Koyama、Yukio Nohara

  DOI：10.1016/j.carres.2020.108171

  日期：2020.12

  Glycosylation, a part of the Maillard reaction, occurs non-enzymatically in food and biological processes. The selectivity of N-glycosylation was analyzed based on the reactivity of monosaccharides with aromatic amines, including aromatic amino acids, and the degree of molecular interaction (MI) measured using liquid chromatography. Furthermore, the chemical structures of reaction products were determined

  糖基化是美拉德反应的一部分，在食品和生物过程中以非酶促方式发生。N-糖基化的选择性基于单糖与芳香胺（包括芳香氨基酸）的反应性以及使用液相色谱测量的分子相互作用 (MI) 程度进行分析。此外，使用 X 射线晶体学和/或 NMR 确定反应产物的化学结构。使用不同构象的优化能量值在计算机中估计可能的反应产物。使用模型相的计算机分析计算氨基和糖类的 MI 能量值。具有较大 MI 值的糖类容易产生稳定的 N-糖苷晶体。葡萄糖（一种能量糖）的反应速度很慢，它很容易产生 Amadori 化合物。芳香胺与糖类反应性的研究、单糖在色谱中氨基相保留的测量以及 N-糖苷的合成以确定其结构将为候选药物的修饰提供有关选择性糖基化的有用信息以提高它们的水溶性。
• Triphenylphosphine Polymer-Bound/Iodine Complex: A Suitable Reagent for the Preparation of<i>O</i>-Isopropylidene Sugar Derivatives
  作者：Giovanni Palumbo、Silvana Pedatella、Annalisa Guaragna、Daniele D’Alonzo、Mauro De Nisco

  DOI：10.1055/s-2005-918521

  日期：——

  O-Isopropylidene derivatives of sugars are readily prepared by using the Lewis acid and dehydrating agent triphenylphosphine polymer-bound/I 2 complex. This new method is characterized by smooth, non-equilibrating reaction conditions and a very clean, simple work-up, making it particularly suitable for O-isopropylidenation of sugars under mild conditions and with low environmental impact.

  使用路易斯酸和脱水剂三苯基膦聚合物结合/I 2 复合物很容易制备糖的 O-异亚丙基衍生物。这种新方法的特点是平稳、非平衡的反应条件和非常干净、简单的后处理，使其特别适用于在温和条件下对糖进行 O-异丙基化，对环境影响低。
• Isomeric equilibria of monosaccharides in solution. Influence of solvent and temperature
  作者：Felix Franks、Peter J. Lillford、Geoffrey Robinson

  DOI：10.1039/f19898502417

  日期：——

  °C in terms of the coexisting anomers, tautomers and conformers. In glucose solutions only 4C1 pyranose forms could be detected, but the temperature dependence of the α/β ratio differs in the two solvents. Ribose solutions consist of mixtures of six species, the relative concentrations of which display complex temperature dependences. The experimental results are discussed in terms of solvation contributions

  通过1 H nmr光谱在0–90°C的温度范围内测定了D 2 O和二甲基亚砜-d 6中D-葡萄糖，D-核糖，β-甲基吡喃葡萄糖苷和β-甲基核吡喃糖苷的平衡混合物的组成。就共存的端基异构体，互变异构体和构象异构体而言。在葡萄糖溶液中，只能检测到4 C 1吡喃糖形式，但α / β的温度依赖性两种溶剂的比例不同。核糖溶液由六种物质的混合物组成，其相对浓度表现出复杂的温度依赖性。根据溶剂化对不同物种的相对自由能的贡献来讨论实验结果。
• Kikuchi, Yasuaki; Tanaka, Yasutaka; Sutarto, Supriyanto, Journal of the American Chemical Society, 1992, vol. 114, # 26, p. 10302 - 10306
  作者：Kikuchi, Yasuaki、Tanaka, Yasutaka、Sutarto, Supriyanto、Kobayashi, Kenji、Toi, Hiroo、Aoyama, Yasuhiro

  DOI：——

  日期：——
• The oxygen-18 isotope shift in carbon-13 NMR spectroscopy. 14. Kinetics of oxygen exchange at the anomeric carbon of D-ribose and D-2-deoxyribose
  作者：Sergio J. Cortes、Tony L. Mega、Robert L. Van Etten

  DOI：10.1021/jo00003a009

  日期：1991.2

  The kinetics of the oxygen-exchange reaction at the anomeric carbon atoms of D-ribose and D-2-deoxyribose (2-deoxy-D-erythro-pentose) were compared using the O-18 isotope induced shift in C-13 NMR spectroscopy. Measurements were made at a number of temperature and pH values. The oxygen-exchange reaction for these sugars is strongly pH-dependent, displaying regions of acid, water, and base catalysis. At 25-degrees-C the oxygen-exchange rate of D-ribose was found to be approximately 20-fold greater than the rate for D-glucose between pH 2 and 9. In turn, the oxygen-exchange rate for D-2-deoxyribose was greater than the rate for D-ribose by approximately 5-fold above pH 4 and by greater than 10-fold below pH 4. The results are analyzed in terms of steric and inductive effects on the hydration kinetics of the open-chain forms and by comparison with the hydration reaction of simple aldehydes. The study also includes quantitative data, based upon C-13 NMR line intensities, for the various anomeric forms that exist in solutions of these sugars at the different temperature and pH values used in the kinetic measurements reported here. In each case, the oxygen-exchange reactions of the anomers are slow relative to the rate of anomerization, so that the anomers appear to exchange oxygen at the same rate.