ethyl α-L-arabinofuranoside | 98524-01-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl α-L-arabinofuranoside
• 英文别名: (2R,3R,4R,5S)-2-ethoxy-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 98524-01-7
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: XESKOQZTIQOBMT-VWDOSNQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  ethyl α-L-arabinofuranoside 在 吡啶 、 盐酸 、 对甲苯磺酰氯 作用下， 生成 (2R,3S,4S)-2-(dimethoxymethyl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  The Chemistry of 2,5-Anhydro-L-arabinose¹

  摘要：

  DOI：

  10.1021/ja01606a038
• 作为产物：
  描述：

  L-阿拉伯糖 在 吡啶 、 sodium hydroxide 、 α-L-arabinofuranosidase (EC 3.2.1.55) 、 硫酸 、 ethanol; compound with boron fluoride 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 生成 ethyl α-L-arabinofuranoside
  参考文献：
  名称：

  Enzymatic synthesis of alkyl arabinofuranosides using a thermostable α-l-arabinofuranosidase

  摘要：

  A thermostable alpha-L-arabinofuranosidase was tested for its ability to perform transglycosylation with different alcohol acceptors. Reactions were characterized by high rates with optimal synthesis being obtained within 10 min. Both primary and secondary alcohols could act as acceptors in transarabinosylation but yields of alkyl arabinosides decreased with increasing alkyl chain length. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02381-x

文献信息

• Araf51 with improved transglycosylation activities: one engineered biocatalyst for one specific acceptor
  作者：Alizé Pennec、Richard Daniellou、Pascal Loyer、Caroline Nugier-Chauvin、Vincent Ferrières

  DOI：10.1016/j.carres.2014.10.031

  日期：2015.1

  were selected on their ability to catalyze the transglycosylation reaction of p-nitrophenyl α-L-arabinofuranoside (pNP-Araf) used as a donor and various aliphatic alcohols as acceptors. This screening strategy underlined 5 interesting clones, each one corresponding to one acceptor. They appeared to be much more efficient in the transglycosylation reaction compared to the wild type enzyme whereas no self-condensation

  为了获得用于合成烷基阿拉伯呋喃糖苷的有效生物催化剂，已经进行了阿拉伯呋喃呋喃糖基水解酶Araf51的随机诱变。选择突变体是基于其催化用作供体的对硝基苯基α-L-阿拉伯呋喃糖苷（pNP-Araf）和各种脂族醇作为受体的转糖基化反应的能力。这种筛选策略强调了5个有趣的克隆，每个克隆对应一个受体。与野生型酶相比，它们在转糖基化反应中似乎更有效，而未检测到自缩合或水解产物。此外，突变体对已为其选择了醇的高特异性证实了筛选过程。突变酶的序列分析表明，
• Environmentally benign glycosylation of aryl pyranosides and aryl/alkyl furanosides demonstrating the versatility of thermostable CGTase from Thermoanaerobacterium sp.
  作者：Alizé Pennec、Laurent Legentil、Luis Herrera-Estrella、Vincent Ferrières、Anne-Laure Chauvin、Caroline Nugier-Chauvin

  DOI：10.1039/c4gc00631c

  日期：——

  The specificity of transglycosylation of Thermoanaerobacterium sp. CGTase against aryl furanosides is reported.

  报道了Thermoanaerobacterium sp. CGTase对芳基呋喃苷的转糖基特异性。
• THE SYNTHESIS OF 5-<i>O</i>-METHYL-<scp>L</scp>-ARABINOSE
  作者：G. G. S. Dutton、Y. Tanaka、K. Yates

  DOI：10.1139/v59-286

  日期：1959.12.1

  hydrolysis products of methylated wheat bran hemicellulose. This sugar has now been synthesized from ethyl 2,3-di-O-acetyl-5-O-trityl-α-L-arabinoside by detritylation, methylation, and hydrolysis. The free sugar was obtained as a sirup and was characterized by periodate oxidation together with the preparation of a crystalline osazone and a crystalline lactone.

  5-O-甲基-L-阿拉伯糖被认为存在于甲基化麦麸半纤维素的水解产物中。这种糖现在已经由乙基 2,3-二-O-乙酰基-5-O-三苯甲基-α-L-阿拉伯糖苷通过脱三苯甲基化、甲基化和水解合成。游离糖以糖浆形式获得，其特征在于高碘酸盐氧化以及结晶 osazone 和结晶内酯的制备。
• Glycofuranosides and Thioglycofuranosides. III. New Crystalline Furanosides of d-Galactose and l-Arabinose
  作者：John W. Green、Eugene Pacsu

  DOI：10.1021/ja01276a011

  日期：1938.9
• Structure of Corn Hull Hemicellulose. Part VI. The Synthesis of 5-O-β-D-Galactopyranosyl-L-arabinose^1,2
  作者：Irwin J. Goldstein、F. Smith、H. C. Srivastava

  DOI：10.1021/ja01571a062

  日期：1957.7