alpha-L-阿拉伯糖呋喃糖 | 38029-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: alpha-L-阿拉伯糖呋喃糖
• 英文名称: α-L-arabinofuranoside
• 英文别名: α-L-arabinofuranose；α-L-arabinose；L-arabinofuranose；L-arabinose；arabinose；alpha-L-arabinofuranose；(2R,3R,4R,5S)-5-(hydroxymethyl)oxolane-2,3,4-triol
• CAS: 38029-69-5
• 化学式: C₅H₁₀O₅
• 分子量: 150.131
• InChiKey: HMFHBZSHGGEWLO-QMKXCQHVSA-N

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：

  alpha-L-阿拉伯糖呋喃糖 在 sodium tetrahydroborate 作用下， 以 ammonium hydroxide 为溶剂， 反应 2.0h， 生成 L-(-)-arabitol
  参考文献：
  名称：

  黑曲霉和刺曲霉内-（1-> 5）-α-L-阿拉伯聚糖酶的底物结合区域的作用模式和作图。

  摘要：

  用还原的和规则的（1-> 5）-α-L-研究了黑曲霉和刺曲霉的内切（1-> 5）-α-L-阿拉伯糖酶（EC 3.2.1.99）的底物结合位点。阿拉伯寡糖和高效阴离子交换色谱分析。对于这些底物的键裂解频率和kcat / K（m）参数的计算使得能够确定阿拉伯呋喃糖基结合亚位点的数目并估计每个亚位点的结合亲和力。刺果曲霉内阿拉伯聚糖酶具​​有在催化位点周围对称排列的六个亚位点，而黑曲霉内阿拉伯聚糖酶具​​有五个亚位点。两个从催化位点朝向结合的底物的非还原端，三个向还原端。两个A中的两个催化位点直接相邻。尼日尔和刺果内阿拉伯聚糖酶具​​有接近零的结合净自由能。这些结果与大多数研究的吡喃葡萄糖基内水解酶不同，后者在这两个亚位处具有净的负（不利）相互作用能，并且可能与吡喃呋喃糖基残基的构象柔韧性更大有关。关于观察到的这些酶在线性（1-> 5）-α-L-阿拉伯糖上的作用模式，还对完整的亚位图进行了合理化处理。

  DOI：

  10.1016/s0008-6215(97)00159-6
• 作为产物：
  描述：

  4-硝基苯基-ALPHA-L-阿拉伯糖甙 在 α-L-arabinofuranosidase from Thermobacillus xylanilyticus 作用下， 以 aq. acetate buffer 为溶剂， 生成 alpha-L-阿拉伯糖呋喃糖
  参考文献：
  名称：

  Enhancing the chemoenzymatic synthesis of arabinosylated xylo-oligosaccharides by GH51 α-l-arabinofuranosidase

  摘要：

  Random mutagenesis was performed on the alpha-L-arabinofuranosidase of Thermobacillus xylanilyticus in order to enhance its ability to perform transarabinofuranosylation using natural xylo-oligosaccharides as acceptors. To achieve this goal, a two-step, high-throughput digital imaging protocol involving a colorimetric substrate was used to screen a library of 30,000 mutants. In the first step this screen selected for hydrolytically-impaired mutants, and in the second step the screen identified mutants whose global activity was improved in the presence of a xylo-oligosaccharide mixture. Thereby, 199 mutants displaying lowered hydrolytic activity and modified properties were detected. In the presence of these xylo-oligosaccharides, most of the 199 (i.e., 70%) enzymes were less inhibited and some (18) mutants displayed an unambiguous alleviation of inhibition (<25% loss of activity). More precise monitoring of reactions catalyzed by the most promising mutants revealed a significant improvement of the synthesis yields of transglycosylation products (up to 18% compared to 9% for the parental enzyme) when xylobiose was present in the reaction. Genetic analysis of improved mutants revealed that many of the amino acid substitutions that correlate with the modified phenotype are located in the vicinity of the active site, particularly in subsite -1. Consequently, we hypothesize that these mutations modify the active site topology or the molecular interaction network of the L-arabinofuranoside donor substrate, thus impairing the hydrolysis and concomitantly favoring transglycosylation onto natural acceptors. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.10.029

文献信息

• Expression, Purification and Characterization of a Bifunctional α-<scp>L</scp>-Arabinofuranosidase/β-<scp>D</scp>-Xylosidase from<i>Trichoderma Koningii</i>G-39
  作者：Chin-Feng Wan、Cheng-Ta Chen、Yaw-Kuen Li、Lina Huang

  DOI：10.1002/jccs.200700018

  日期：2007.2

  cation-exchanged chromatography. The purified enzyme exhibits both a-L-arabinofuranosidase and β-D-xylosidase (Xyl) activities with p-nitrophenyl-a-L-arabionfuranoside (pNPAF) and 2,4-dinitrophenyl-β-D-xylopyanoside (2,4-DNPX) as substrate, respectively. The stability and the catalytic feature of the bifunctional enzyme were characterized. The enzyme was stable for at least 2 h at pH values between 2 and

  来自科宁木霉 G-39 的 aL-阿拉伯呋喃糖苷酶 (Abf) 基因在毕赤酵母中成功表达。通过阳离子交换色谱法将重组酶纯化至> 90%同质性。纯化的酶以对硝基苯基-α-L-阿拉伯呋喃糖苷 (pNPAF) 和 2,4-二硝基苯基-β-D-木糖苷 (2,4-DNPX) 作为底物，同时具有 aL-阿拉伯呋喃糖苷酶和 β-D-木糖苷酶 (Xyl) 活性， 分别。表征了双功能酶的稳定性和催化特性。当测定 Abf 和 Xyl 活性时，该酶在室温下在 2 和 8.3 之间的 pH 值下稳定至少 2 小时。当 pH 值超过 9.5 或降至 1.5 以下时，酶活性急剧下降。该酶在 55°C 孵育 2 小时后失去 35% 的 Abf 活性，但保留了 95% 的 Xyl 活性，其中 2, 以4-DNXP为底物，条件相同。通过酶活性的抑制研究对两种酶功能的活性位点拓扑结构进行了进一步研究。结果表明，甲基-α-L-阿拉伯呋喃糖苷抑制对作为底物的
• Synthesis of β-1,4-Linked Galactan Side-Chains of Rhamnogalacturonan I
  作者：Mathias C. F. Andersen、Stjepan K. Kračun、Maja G. Rydahl、William G. T. Willats、Mads H. Clausen

  DOI：10.1002/chem.201602197

  日期：2016.8.8

  The synthesis of linear‐ and (1→6)‐branched β‐(1→4)‐d‐galactans, side‐chains of the pectic polysaccharide rhamnogalacturonan I is described. The strategy relies on iterative couplings of n‐pentenyl disaccharides followed by a late stage glycosylation of a common hexasaccharide core. Reaction with a covalent linker and immobilization on N‐hydroxysuccinimide (NHS)‐modified glass surfaces allows the generation

  直链的和合成（1→6） -支化的β-（1→4） - d -galactans，鼠李我描述了果胶多糖的侧链。该策略依赖于正戊烯基二糖的迭代偶联，随后是常见六糖核心的晚期糖基化。与共价接头反应并固定在N-羟基琥珀酰亚胺（NHS）修饰的玻璃表面上可以生成碳水化合物微阵列。聚糖阵列能够以高通量的方式研究蛋白质与碳水化合物的相互作用，本文通过mAb和CBM的结合研究证明了这一点。
• 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，
• 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。
• Production, purification, and properties of an α-l-arabinofuranosidase from Cihomitus squalens
  作者：Jean-Marc Brillouet、Jean-Claude Moulin、Eduardo Agosin

  DOI：10.1016/0008-6215(85)85012-6

  日期：1985.11

  Abstract A white-rot fungus Dichomitus squalens , when grown on 1% wheat-straw glucuronoarabinoxylan under aerated submerged conditions, secreted an α- l -arabinofuranosidase (4.3 nkat/mL). The enzyme was purified 70-fold by ammonium sulfate precipitation, chromatofocusing on PBE 94, gel filtration on Ultrogel AcA 54, rechromatofocusing on PBE 94, and lectin affinity chromatography on Concanavalin

  摘要白腐真菌角叉菜（Dchomitus squalens）在曝气条件下在1％的麦草葡糖醛酸阿拉伯糖基木聚糖上生长时，会分泌α-1-α-阿拉伯呋喃糖苷酶（4.3 nkat / mL）。通过硫酸铵沉淀，在PBE 94上进行色谱聚焦，在Ultrogel AcA 54上进行凝胶过滤，在PBE 94上进行重新色谱聚焦以及在伴刀豆球蛋白A-Ultrogel上的凝集素亲和色谱对酶进行70倍纯化。该酶是一种糖蛋白，分子量为60,000，pI为5.1。该酶在pH 3.5和60°时显示最大活性，并在70°下30分钟内完全灭活。对-硝基苯基α-1-α-呋喃糖苷的K m值为1.64mm。α-1-阿拉伯呋喃糖苷酶从甜菜阿拉伯糖，小麦秸秆和燕麦拼写的阿拉伯木聚糖以及麦麸杂木聚糖中释放出阿拉伯糖，并且对阿拉伯树胶无活性。