beta-D-吡喃木糖 | 2460-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: beta-D-吡喃木糖
• 英文名称: β-D-xylopyranoside
• 英文别名: D-xylose；β-D-xylose；xylose；β-D-xylopyranose；β-xylose；β-D-Lyxose；Beta-D-Xylopyranose；(2R,3R,4S,5R)-oxane-2,3,4,5-tetrol
• CAS: 2460-44-8
• 化学式: C₅H₁₀O₅
• 分子量: 150.131
• InChiKey: SRBFZHDQGSBBOR-KKQCNMDGSA-N

物化性质

• 熔点：
  203-204 °C
• 沸点：
  333.2±42.0 °C(Predicted)
• 密度：
  1.757±0.06 g/cm3(Predicted)

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

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  beta-D-吡喃木糖 在 hydrotalcite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 (2-呋喃亚甲基)丙二腈
  参考文献：
  名称：

  One-pot synthesis of furfural derivatives from pentoses using solid acid and base catalysts

  摘要：

  一锅法合成(2-呋喃亚甲基)马来酰亚胺，即呋喃醛与马来酰亚胺的Knoevenagel产物，通过联合使用Amberlyst-15酸和Cr/hydrotalcites酸碱催化剂，有效地从木糖中产生44%的产率。

  DOI：

  10.1039/c3cy00980g
• 作为产物：
  描述：

  4-硝基苯基-BETA-D-吡喃木糖苷 在 CAZyme xylosidase 1 from Lucigen 、 sodium succinate 作用下， 生成 beta-D-吡喃木糖
  参考文献：
  名称：

  Rehabilitation of faulty kinetic determinations and misassigned glycoside hydrolase family of retaining mechanism β-xylosidases

  摘要：

  We obtained Cx1 from a commercial supplier, whose catalog listed it as a beta-xylosidase of glycoside hydrolase family 43. NMR experiments indicate retention of anomeric configuration in its reaction stereochemistry, opposing the assignment of GH43, which follows an inverting mechanism. Partial protein sequencing indicates Cx1 is similar to but not identical to beta-xylosidases of GH52, including Q09LZ0, that have retaining mechanisms. Q09LZ0 beta-xylosidase had been characterized biochemically in kinetic reactions that contained Tris. We overproduced Q09LZO and demonstrated that Tris is a competitive inhibitor of the beta-xylosidase. Also, the previous work used grossly incorrect extinction coefficients for product 4-nitrophenol. We redetermined kinetic parameters using reactions that omitted Tris and using correct extinction coefficients for 4-nitrophenol. Cx1 and Q09LZ0 beta-xylosidases were thus shown to possess similar kinetic properties when acting on 4-nitrophenyl-3-D-xylopyranoside and xylobiose. k(cat) pH profiles of Cx1 and Q09LZO acting on 4-nitrophenyl-beta-D-xylopyranoside and xylobiose have patterns containing two rate increases with increasing acidity, not reported before for glycoside hydrolases. The dexylosylation step of 4-nitrophenyl-beta-D-xylopyranoside hydrolysis mediated by Q09LZO is not rate determining for k(cat)(4NPX). Published by Elsevier Inc.

  DOI：

  10.1016/j.abb.2013.07.020

文献信息

• Nitrosation of Sugar Oximes: Preparation of 2-Glycosyl-1-hydroxydiazene-2-oxides
  作者：Jörg Brand、Thomas Huhn、Ulrich Groth、Johannes C. Jochims

  DOI：10.1002/chem.200500325

  日期：2006.1

  Oximes of glucose, xylose, lactose, fructose, and mannose have been prepared. Nitrosation of the oximes of glucose, xylose, and lactose with NaNO2/HCl afforded 2-(beta-glycopyranosyl)-1-hydroxydiazene-2-oxides, which were isolated as salts 13, 22, and 28. Nitrosation of fructose oxime 29 furnished fructose, whereas nitrosation of mannose oxime 30 with NaNO2/HCl afforded the 1-hydroxy-2-(beta-D-man

  已经制备了葡萄糖，木糖，乳糖，果糖和甘露糖的肟。用NaNO 2 / HCl亚硝化葡萄糖，木糖和乳糖的肟，得到2-（β-甘露糖基）-1-羟基二氮杂-2-氧化物，其被分离为盐13、22和28。提供了果糖肟的亚硝化29果糖，而甘露糖肟30用NaNO2 / HCl的亚硝化得到1-羟基-2-（β-D-甘露吡喃糖基）二氮杂-2-氧化物32，由此制得对茴香醚鎓盐31和钠盐33。然而，在CsOH或KOH的水溶液中用亚硝酸异戊酯亚硝化30，导致分别形成2-（α-D-甘露呋喃糖基）-1-羟基二氮杂2-氧化物盐34和35。2-（β-D-吡喃葡萄糖基）-1-羟基二氮杂-2-氧化物铵13的甲基化产生1-甲氧基化合物，将其苯甲酰化得到四-O-苯甲酸酯14a，通过X射线衍射分析证实其结构。由葡萄糖O-甲基肟15和16制备N-甲氧基-N-亚硝基-2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖胺18。该化合物的结构通过
• Acid-Catalyzed Conversion of Xylose in Methanol-Rich Medium as Part of Biorefinery
  作者：Xun Hu、Caroline Lievens、Chun-Zhu Li

  DOI：10.1002/cssc.201100745

  日期：2012.8

  treatments of xylose have been performed in a methanol/water mixture to investigate the reaction pathways of xylose during bio‐oil esterification. Xylose was mainly converted into methyl xylosides with negligible humins formed below 130 °C. However, humins formation became significant with the dehydration of xylose to furfural and 2‐(dimethoxymethyl)furan (DOF) at elevated temperatures. The conversion of xylose

  木糖酸处理已在甲醇/水混合物中进行，以研究木糖在生物油酯化过程中的反应途径。木糖主要转化为甲基木糖化物，在低于130°C时形成的腐殖质可忽略不计。然而，在高温下，木糖脱水成糠醛和2-（二甲氧基甲基）呋喃（DOF）后，腐殖质的形成变得很重要。木糖转化为甲基木糖苷可以保护木糖的C1羟基，从而稳定木糖并抑制糖低聚物的形成和聚合反应。相比之下，糠醛向DOF的转化保护了糠醛的羰基。然而，由于反应平衡从DOF转移到糠醛，且停留时间延长，因此在高温下该保护作用并未显着抑制糠醛的聚合。此外，糠醛的酸处理在甲醇中产生了乙酰丙酸甲酯，在水中产生了乙酰丙酸，甲酸被甲酸催化。
• 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
• 13C CP MAS NMR and crystal structure of methyl glycopyranosides
  作者：Katarzyna Paradowska、Tomasz Gubica、Andrzej Temeriusz、Michał K. Cyrański、Iwona Wawer

  DOI：10.1016/j.carres.2008.05.015

  日期：2008.9

  The X-ray diffraction analysis, (13)C CP MAS NMR spectra and powder X-ray diffraction patterns were obtained for selected methyl glycosides: alpha- and beta-d-lyxopyranosides (1, 2), alpha- and beta-l-arabinopyranosides (3, 4), alpha- and beta-d-xylopyranosides (5, 6) and beta-d-ribopyranoside (7) and the results were confirmed by GIAO DFT calculations of shielding constants. In X-ray diffraction analysis

  对于选定的甲基糖苷，获得了X射线衍射分析，（13）CP CP MAS NMR光谱和粉末X射线衍射图：α-和β-d-lyxopyranosides（1、2），α-和β-1-阿拉伯吡喃糖苷（3、4），α-和β-d-吡喃吡喃糖苷（5、6）和β-d-核吡喃吡喃糖苷（7），其结果通过GIAO DFT计算屏蔽常数得到了证实。在1和2的X射线衍射分析中，由于异头效应，在1的分子中观察到所选键的特征缩短和延长，并且在1和2的晶格中观察到不同图案的氢键。另外，在1中观察到了另外一个具有环氧原子参与的分子内氢键。固态和溶液之间观察到的化学位移差异来自构象效应和各种分子间氢键的形成。源于分子间氢键的化学位移变化的幅度小于构象效应。此外，对4、5和7进行的粉末X射线衍射（PXRD）显示，7以两种多晶型物的混合物形式存在，其中之一可能由两个非等价分子组成。
• Marine natural products. VIII. Bioactive triterpene-oligoglycosides from the sea cucumber Holothuria leucospilota Brandt (2). Structure of holothurin A.
  作者：ISAO KITAGAWA、TAKAO NISHINO、MOTOMASA KOBAYASHI、YOSHIMASA KYOGOKU

  DOI：10.1248/cpb.29.1951

  日期：——

  The chemical structure of holothurin A, the major lanostane-type triterpene oligoglycoside from the Cuvierian tubules of the sea cucumber Holothuria leucospilota BRANDT (=H. vagabunda SELENKA), has been elucidated to be 3-O-[β-D-3-O-methylglucopyranosyl-(1→3)-β-D-glucopyranosyl (1→4)-β-D-quinovopyranosyl (1→2)-β-D-xylopyranosyl]-holothurigenol 4'-O-sodium sulfate (8), on the basis of chemical, physicochemical, and biochemical evidence. Holothurin A (8) corresponds to the 4"-O-[3'''-O-(β-D-3''''-O-methyl-glucopyranosyl)-β-D-glucopyranoside] of holothurin B (6), which is the major oligoglycoside of the body walls of the same sea cucumber.

  海参Holothuria leucospilota BRANDT (=H. vagabunda SELENKA)的Cuvierian管中的主要羊毛甾烷型三萜寡糖苷holothurin A的化学结构已被阐明为3-O-[β-D-3-O-甲基葡萄糖吡喃糖苷-(1→3)-β-D-葡萄糖吡喃糖苷(1→4)-β-D-奎诺糖吡喃糖苷(1→2)-β-D-木糖吡喃糖苷]-holothurigenol 4'-O-硫酸钠(8)，这一结论基于化学、物理化学和生物化学证据。Holothurin A (8)对应于holothurin B (6)的4"-O-[3'''-O-(β-D-3''''-O-甲基-葡萄糖吡喃糖苷)-β-D-葡萄糖苷]，后者是同一种海参体壁中的主要寡糖苷。