α-naphthyl β-D-ribofuranoside | 64691-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-naphthyl β-D-ribofuranoside
• 英文别名: alpha-naphthyl beta-D-ribofuranoside；(2R,3S,4R,5S)-2-(hydroxymethyl)-5-naphthalen-1-yloxyoxolane-3,4-diol
• CAS: 64691-29-8
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: DBZXYTVLAWGLKX-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-naphthyl β-D-ribofuranoside 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以57%的产率得到pyridin-3-yl β-D-ribofuranoside
  参考文献：
  名称：

  ENZYME DETECTION/ASSAY METHOD AND SUBSTRATES

  摘要：

  该发明涉及一种使用显色底物检测和/或测定核苷水解酶或核苷酸磷酸酶的方法。首选的显色底物具有式(I)，其中X为OH或H，Y为Y—OH的残基，其中Y—OH为色团或易于转化为色团的化合物，这些底物通过核苷水解酶水解产生核糖或2-脱氧核糖以及Y—OH。或者这些底物可能被核苷酸磷酸酶磷酸化产生核糖-1-磷酸加Y—OH。这些方法可用于检测和/或测定生物样本中的寄生虫。

  公开号：

  US20010019823A1
• 作为产物：
  描述：

  2,3,5-tri-O-pentanoyl-1-O-(1-naphthyl)-β-D-ribofuranoside 在 甲醇 、 氨 作用下， 生成 α-naphthyl β-D-ribofuranoside
  参考文献：
  名称：

  Effect of acyl chain length on selective biocatalytic deacylation on O-aryl glycosides and separation of anomers

  摘要：

  It has been demonstrated that Lipozyme (R) TL IM (Thermomyces lanuginosus lipase immobilised on silica) can selectively deacylate the ester function involving the C-5' hydroxyl group of alpha-anomers over the other acyl functions of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranoside. The analysis of results of biocatalytic deacylation reaction revealed that the reaction time decreases with the increase in the acyl chain length from C-1 to C-4. The unique selectivity of Lipozyme (R) TL IM has been harnessed for the separation of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranosides, The lipase mediated selective deacylation methodology has been used for the synthesis of O-aryl alpha-D-ribofuranosides and O-aryl beta-D-ribofuranosides in pure forms, which can be used as chromogenic substrate for the detection of pathogenic microbial parasites containing glycosidases. (C) 2014 Published by Elsevier Inc.

  DOI：

  10.1016/j.bioorg.2014.02.004

文献信息

• O-Aryl α,β-d-ribofuranosides: Synthesis & highly efficient biocatalytic separation of anomers and evaluation of their Src kinase inhibitory activity
  作者：Raman K. Sharma、Sukhdev Singh、Rakesh Tiwari、Deendayal Mandal、Carl E. Olsen、Virinder S. Parmar、Keykavous Parang、Ashok K. Prasad

  DOI：10.1016/j.bmc.2012.09.057

  日期：2012.12

  A series of peracetylated O-aryl α,β-d-ribofuranosides have been synthesized and an efficient biocatalytic methodology has been developed for the separation of their anomers which was otherwise almost impossible by column chromatographic or other techniques. The incubation of 2,3,5-tri-O-acetyl-1-O-aryl-α,β-d-ribofuranoside with Lipozyme® TL IM immobilized on silica led to the selective deacetylation

  已经合成了一系列过乙酰化的O-芳基α，β- d-核呋喃糖苷，并且已经开发了用于分离其端基异构体的有效的生物催化方法，否则通过柱色谱法或其他技术几乎是不可能的。将2,3,5-三-O-乙酰基-1- O-芳基-α，β- d-核呋喃糖苷与固定在硅胶上的Lipozyme®TL IM一起孵育仅导致一个乙酰氧基的选择性脱乙酰，即C -5′- Oα-端基异构体的-乙酰氧基高于分子中存在的两个仲羟基衍生的其他乙酰氧基，也超过三个乙酰基基团（源自β-端基异构体的一个伯羟基和两个仲羟基）。该方法导致容易合成O-芳基d-核呋喃呋喃糖苷的α-和β-端基异构体。筛选所有的芳基呋喃核糖苷抑制Src激酶。1 - O-（3-甲氧基苯基）-β- d-核呋喃糖苷显示出最高的抑制Src激酶的活性（IC 50  = 95.0μM ）。
• Enzyme detection/assay method and substrates
  申请人：——

  公开号：US20020132263A1

  公开（公告）日：2002-09-19

  The invention relates to a method of detecting and/or assaying nucleoside hydrolases or nucleoside phosphorylases using a chromogenic substrate. Preferred chromogenic substrates have formula (I) where X is OH, or H, and Y is the residue of Y—OH where Y—OH is a chromophore or a compound readily converted to a chromophore and the substrates are hydrolysed by the nucleoside hydrolase to yield ribose or 2-deoxyribose plus Y—OH. Alternatively those substrates may be phosphorylysed by nucleoside phosphorylase to yield ribose-1-phosphate plus Y—OH. The methods may be used to detect and/or assay parasites in biological samples. 1

  本发明涉及使用显色底物检测和/或测定核苷酸酶或核苷酸磷酸酶的方法。首选显色底物具有公式（I），其中X是OH或H，Y是Y-OH残基，其中Y-OH是一种色团或易于转化为色团的化合物，底物通过核苷酸酶水解产生核糖或2-去氧核糖加上Y-OH。或者，这些底物可被核苷酸磷酸酶磷酸化，形成核糖1-磷酸加上Y-OH。该方法可用于检测和/或测定生物样品中的寄生虫。
• REACTION MEDIUM FOR DETECTING AND/OR IDENTTIFYING STAPHYLOCCOUS AUREUS
  申请人：Halimi Diane

  公开号：US20100297692A1

  公开（公告）日：2010-11-25

  A reaction medium for characterizing Staphylococcus aureus , that includes a metabolic indicator which is a beta-ribosidase substrate in combination with at least one other metabolic indicator and/or at least one metabolic regulator. A method for detecting and/or identifying Staphylococcus aureus , including: providing a reaction medium that comprises a metabolic indicator which is a beta-ribosidase substrate in combination with at least one other metabolic indicator and/or at least one metabolic regulator; inoculating the medium with a biological sample to be tested; allowing for incubation; and characterizing the presence of Staphylococcus aureus.
• US6379911B2
  申请人：——

  公开号：US6379911B2

  公开（公告）日：2002-04-30
• US6764829B2
  申请人：——

  公开号：US6764829B2

  公开（公告）日：2004-07-20