beta-D-阿拉伯糖呋喃糖 | 25545-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: beta-D-阿拉伯糖呋喃糖
• 英文名称: β-D-arabinofuranose
• 英文别名: D-arabinose；β-D-arabinose；β-Arabinose；beta-D-arabinofuranose；(2R,3S,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol
• CAS: 25545-03-3
• 化学式: C₅H₁₀O₅
• 分子量: 150.131
• InChiKey: HMFHBZSHGGEWLO-SQOUGZDYSA-N

物化性质

• 沸点：
  375.4±42.0 °C(Predicted)
• 密度：
  1.681±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  10
• 可旋转键数：
  1
• 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

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  beta-D-阿拉伯糖呋喃糖 在 盐酸 作用下， 生成 methyl tri-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis and Antiviral Properties of Arabino and Ribonucleosides of 1,3‐Dideazaadenine, 4‐Nitro‐1, 3‐dideazaadenine and Diketopiperazine

  摘要：

  Different arabinosides and ribosides, viz. Ara-DDA or 9(1-beta-(D)-arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-beta-D-arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or I(1-beta-D-arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-beta-D-ribofuranosyl) 1,3-dideazaadenine (9) and Ribo-NDDP or 9(1-beta-D-ribofuranosyl) 4-nitro-1,3-dideazapurine (10) have been synthesized as probable antiviral agents. The arabinosides have been synthesized using the catalyst TDA-1 that causes stereospecific formation of beta-nucleosides while a one-pot synthesis procedure was adopted for the synthesis of the ribonucleosides where beta-anomers were obtained in higher yields. All the five nucleoside analogs have been screened for antiviral property against HIV-1 ((IIIB)), HSV-1 and 2, parainfluenza-3, reovirus-1 and many others. It was observed that arabinosides had greater inhibitory action than ribosides. The compound 7 or Ara-NDDP has shown maximum inhibition of HIV-1 replication than the rest of the molecules with an IC50 of 79.4 mug/mL.

  DOI：

  10.1081/ncn-200040614
• 作为产物：
  描述：

  阿卡地新 在 盐酸 、 三氯氧磷 作用下， 以 吡啶 、 氯仿 、 重水 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 beta-D-阿拉伯糖呋喃糖
  参考文献：
  名称：

  1-Methylisoguanosine, a pharmacologically active agent from a marine sponge

  摘要：

  DOI：

  10.1021/jo01308a015

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。
• Determination of the absolute configuration of monosaccharides by 1H NMR spectroscopy of their per-O-(S)-2-methylbutyrate derivatives
  作者：William S. York、Stephen Hantus、Peter Albersheim、Alan G. Darvill

  DOI：10.1016/s0008-6215(97)00050-5

  日期：1997.5

  Abstract An empirical method was developed to determine the absolute configuration of monosaccharides, based on high-field 1H NMR spectroscopy of their per- O-(S)-2-methylbutyrate (SMB) derivatives. The SMB derivatives of the D and L forms of a given monosaccharide are diastereomers, allowing them to be distinguished on the basis of differences in their 1H NMR chemical shifts. The reproducibility of

  摘要建立了一种基于经验的方法来确定其单糖的绝对构型，该方法基于其过O-（S）-2-甲基丁酸酯（SMB）衍生物的1H NMR光谱。给定单糖的D和L形式的SMB衍生物为非对映异构体，可根据其1H NMR化学位移的差异进行区分。这些化学位移差异的可重复性可以通过比较数据库中SMB衍生物的光谱与标准光谱来常规确定各种单糖的绝对构型，从而无需为每次分析准备和分析新的标准。衍生过程使用廉价，易于处理的试剂，并且实际上是完整的。将该方法应用于三种复杂的聚糖，可以明确确定其组成单糖的绝对构型。几种单糖的对映体形式可通过其过-O-（S）-2-甲基丁酸酯衍生物的高场1H NMR光谱进行区分。
• Acid Mediated Hydrolysis of Blueberry Anthocyanins.
  作者：Takashi ICHIYANAGI、Kikuo OIKAWA、Chigusa TATEYAMA、Tetsuya KONISHI

  DOI：10.1248/cpb.49.114

  日期：——

  Acid mediated hydrolysis of anthocyanins was studied using capillary zone electrophoresis (CZE). A commercially available wild blueberry (Bilberry) extract was dissolved in different concentrations of TFA (0.1, 1, 3, 9%), then was subjected to thermodecomposition reaction at 95 °C. After the reaction, the samples were analyzed by CZE. The hydrolysis rate of each anthocyanin and the formation of the aglycon were determined by the change in the peak pattern of the anthocyanins in the electropherogram. Each anthocyanin peak decreased time dependently in a first order kinetic fashion. It was revealed that the hydrolysis rate of each anthocyanin was determined primarily by the type of conjugated sugar and not by the aglycon structure. The rate constant of anthocyanin hydrolysis was in the following order, arabinoside>galactoside>glucoside without regard to the aglycon structure. The kinetic behavior of this anthocyanin hydrolysis together with the CZE mobility allowed us to identify an unknown CZE peak as delphinidin 3-O-β-arabinoside. At low TFA concentration, significant decomposition of the anthocyanidin nucleus occurred, but the glycoside hydrolysis predominated at high TFA concentration. It was further revealed that the aglycon released reacted successively to form polymeric products at higher TFA conditions.

  使用毛细管区带电泳 (CZE) 研究了酸介导的花青素水解。将市售的野生蓝莓（Bilberry）提取物溶解在不同浓度的TFA（0.1、1、3、9%）中，然后在95℃下进行热分解反应。反应后，通过 CZE 分析样品。通过电泳图中花青素峰模式的变化来确定每种花青素的水解速率和苷元的形成。每个花青素峰以一级动力学方式随时间下降。结果表明，每种花青素的水解率主要由共轭糖的类型决定，而不是由苷元结构决定。花青素水解速率常数的顺序为：阿拉伯糖苷>半乳糖苷>葡萄糖苷，与苷元结构无关。这种花青素水解的动力学行为以及 CZE 迁移率使我们能够将未知的 CZE 峰识别为花翠素 3-O-β-阿拉伯糖苷。在低TFA浓度下，花青素核发生显着分解，但在高TFA浓度下糖苷水解占主导地位。进一步揭示，释放的苷元在较高的TFA条件下连续反应形成聚合产物。
• Facile Synthesis of 5-Substituted Arabinofuranosyluracil Derivatives
  作者：Hiroaki Sawai、Hidekazu Hayashi、Sumie Sekiguchi

  DOI：10.1246/cl.1994.605

  日期：1994.3

  Arabinoaminooxazoline reacted readily with α-(bromomethyl)acrylate derivatives to afford the corresponding adduct. Potassium tert-butoxide- or sodium methoxide-catalyzed cyclization of the adduct gave 5-substituted 2,2′-anhydroarabinofuranosyluracil derivatives.

  阿拉伯氨基恶唑啉很容易与α-（溴甲基）丙烯酸酯衍生物反应，得到相应的加合物。叔丁醇钾或甲醇钠催化的加合物环化得到 5-取代的 2,2'-脱水阿拉伯呋喃糖尿嘧啶衍生物。
• Six new dihydrobenzofuran lignans from the branches and leaves of Illicium wardii and their cytotoxic activities
  作者：Feng-mei Ye、Yang-guo Xie、Jie Ren、Ji Ye、Yi-gong Guo、Shi-Kai Yan、Hui-Zi Jin、Wei-Dong Zhang

  DOI：10.1016/j.phytol.2016.07.010

  日期：2016.9

  Six new dihydrobenzofuran lignans, named illiciumlignans A⿿F (compounds 1⿿6), along with 15 known compounds (7⿿21) were isolated from the branches and leaves of Illicium wardii. The structures of 1⿿6 were determined using a combination of 1D and 2D NMR, HR-ESI⿿-MS, and CD spectroscopic data. Illiciumlignan D (4) is the first reported dihydrobenzofuran lignan arabinofuranoside that is derivatized with

  六个新的二氢苯并呋喃木脂素，命名为illiciumlignansA⿿F（化合物1⿿6）中，用15种已知化合物（沿7 ⿿ 21）获自的枝叶分离八角wardii。的结构1⿿6使用一维和二维NMR，HR-ESI⿿-MS，和CD光谱数据的组合进行了测定。Illiciumlignan D（4）是第一个报道的二氢苯并呋喃木脂素阿拉伯呋喃糖苷，它被C-9上的阿拉伯呋喃糖部分衍生。化合物1 ⿿ 21针对四种人类肿瘤细胞株的细胞毒活性进行评价。化合物8，12和20具有抗人类癌细胞系（A549，SKOV3，HepG2和HCT116）的显着活性，IC 50值为2.7至14.9μM。