α-1,6-xylopyranose-β-1,4-glucopyranose-(α-1,6-xylopyranose)-β-1,4-glucopyranose-(α-1,6-xylopyranose)-β-1,4-glucopyranose-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-1,6-xylopyranose-β-1,4-glucopyranose-(α-1,6-xylopyranose)-β-1,4-glucopyranose-(α-1,6-xylopyranose)-β-1,4-glucopyranose-glucopyranose
• 英文别名: α-D-xylopyranosyl-(1->6)-β-D-glucopyranosyl-(1->4)-[α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-β-D-glucopyranose；[(Xylα1-6)Glcβ1-4]3Glc；Xyl(a1-6)Glc(b1-4)[Xyl(a1-6)]Glc(b1-4)[Xyl(a1-6)]Glc(b1-4)Glc；(3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-[[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-[[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol
• 化学式: C₃₉H₆₆O₃₃
• 分子量: 1062.93
• InChiKey: PZUPAGRIHCRVKN-QIEBSZABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.2
• 重原子数：
  72
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  525
• 氢给体数：
  20
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  α-1,6-xylopyranose-β-1,4-glucopyranose-(α-1,6-xylopyranose)-β-1,4-glucopyranose-(α-1,6-xylopyranose)-β-1,4-glucopyranose-glucopyranose 在 sodium azide 、 2-氯-1,3-二甲基氯化咪唑啉 、 N,N-二异丙基乙胺 作用下， 以 重水 为溶剂， 反应 1.5h， 以63%的产率得到α-D-xylopyranosyl-(1->6)-β-D-glucopyranosyl-(1->4)-[α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-β-D-glucopyranosyl azide
  参考文献：
  名称：

  One-step conversion of unprotected sugars to β-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution

  摘要：

  在 2-氯-1,3-二甲基氯化咪唑啉（DMC）的介导下，通过非保护糖和叠氮化钠的反应，在水中直接合成了各种δ-糖基叠氮化物。

  DOI：

  10.1039/b905761g
• 作为产物：
  描述：

  (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6S)-6-[(4,6-dimethoxy-1,3,5-triazin-2-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-[[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-3-yl]oxy-4,5-dihydroxy-2-[[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-3-yl]oxy-6-[[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol 在 endo-β-1,4-glucanase III from Trichoderma reesei 、 水 作用下， 生成 α-1,6-xylopyranose-β-1,4-glucopyranose-(α-1,6-xylopyranose)-β-1,4-glucopyranose-(α-1,6-xylopyranose)-β-1,4-glucopyranose-glucopyranose 、 4,6-二甲氧基-1,3,5-三嗪-2(1H)-酮
  参考文献：
  名称：

  4,6-Dimethoxy-1,3,5-triazine oligoxyloglucans: Novel one-step preparable substrates for studying action of endo-β-1,4-glucanase III from Trichoderma reesei

  摘要：

  Two kinds of 4,6-dimethoxy-1,3,5-triazine (DMT) oligoxyloglucans, DMT-beta-XXXG and DMT-beta-XLLG, have been synthesized via one-step procedure starting from the corresponding unprotected oligoxyloglucans in water. The resulting DMT derivatives were found to be hydrolyzed by endo-beta-1,4-D-glucanase III from Trichoderma reesei (EGIII) and utilized as substrates for determination of the kinetic parameters of EGIII. The present DMT-method would be a convenient analytical tool for studying the action of glycosyl hydrolases due to the extremely simple synthetic process of DMT-glycosides without using protecting groups. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.122

文献信息

• Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry
  作者：Yasuhiro Meguro、Masato Noguchi、Gefei Li、Shin-ichiro Shoda

  DOI：10.1021/acs.orglett.7b03400

  日期：2018.1.5

  thiosulfates have been discovered as a new class of synthetic intermediates in sugar chemistry, named “glycosyl Bunte salts” after 19th-century German chemist, Hans Bunte. The synthesis was achieved by direct condensation of unprotected sugars and sodium thiosulfate using a formamidine-type dehydrating agent in water–acetonitrile mixed solvent. The application of glycosyl Bunte salts is demonstrated with transformation

  S-糖基硫代硫酸盐已被发现是糖化学中的一类新型合成中间体，以19世纪德国化学家汉斯·邦特（Hans Bunte）的名字命名为“糖基邦特盐”。通过在水-乙腈混合溶剂中使用甲am型脱水剂将未保护的糖和硫代硫酸钠直接缩合来完成合成。通过向其他糖基化合物如1-硫糖，糖基二硫化物，1，6-脱水糖和O-糖苷的转化反应证明了糖基邦特盐的应用。
• [EN] XYLOGLUCAN-CONTAINING PRODRUGS AND METHODS OF MANUFACTURE AND USE THEREOF<br/>[FR] PROMÉDICAMENTS CONTENANT DU XYLOGLUCANE ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2020198878A1

  公开（公告）日：2020-10-08

  The present application provides compounds, compositions and methods to reduce, alleviate or treat various enteric diseases and disorders, such as inflammatory bowel disease. The compounds are xyloglucan-containing prodrugs, referred to herein as glyco-caged prodrugs, of formula (I) or (II), xyloglucan-β-O-RD (I), xyloglucan-β-O-LSI-RD (II).

  本申请提供了化合物、组合物和方法，用于减少、缓解或治疗各种肠道疾病和紊乱，如炎症性肠病。这些化合物是含有木聚糖的前药，本文中称为糖基封存前药，其化学式为(I)或(II)，木聚糖-β-O-RD (I)，木聚糖-β-O-LSI-RD (II)。
• Synthesis and Analysis of Specific Covalent Inhibitors of<i>endo</i>-Xyloglucanases
  作者：Thomas Hauch Fenger、Harry Brumer

  DOI：10.1002/cbic.201402663

  日期：2015.3.2

  Affinity labels: A series of N‐bromoacetylglycosylamines and bromoketone C‐glycosides of complex xyloglucan oligosaccharides were synthesised and applied as efficient affinity labels for endo‐xyloglucanases. Thanks to their facile production and efficiency of inhibition, the new compounds are well‐suited for detailed enzymological, proteomic, and structural biological analyses of new and known endo‐(xylo)glucanases

  亲和标记：合成了一系列复杂木葡聚糖寡糖的N-溴乙酰基糖胺和溴酮C-糖苷，并用作内木葡聚糖酶的有效亲和标记。由于它们的简便生产和抑制效率，这些新化合物非常适合对新的和已知的内（木糖）内葡聚糖酶进行详细的酶学，蛋白质组学和结构生物学分析。
• NMR Spectroscopic Analysis Reveals Extensive Binding Interactions of Complex Xyloglucan Oligosaccharides with the<i>Cellvibrio japonicus</i>Glycoside Hydrolase Family 31 α-Xylosidase
  作者：Alba Silipo、Johan Larsbrink、Roberta Marchetti、Rosa Lanzetta、Harry Brumer、Antonio Molinaro

  DOI：10.1002/chem.201200488

  日期：2012.10.15

  domain, unique among glycoside hydrolase family 31 members, may confer specificity for large oligosaccharide fragments of the ubiquitous plant polysaccharide xyloglucan (J. Larsbrink, A. Izumi, F. M. Ibatullin, A. Nakhai, H. J. Gilbert, G. J. Davies, H. Brumer, Biochem. J. 2011, 436, 567–580). In the present study, a combination of NMR spectroscopic techniques, including saturation transfer difference

  糖苷水解酶与其底物相互作用的研究是医学，食品和饲料生产以及生物质资源利用中各种应用的基础。最近来自土壤腐生植物日本弧菌的α-木糖苷酶Cj Xyl31A的分子模型，以及蛋白质晶体学和酶动力学分析表明，在糖苷水解酶家族31个成员中独特的附加PA14蛋白结构域可赋予大寡糖特异性无所不在的植物多糖木葡聚糖（J. Larsbrink，A.和泉，FM Ibatullin，A. Nakhai，HJ吉尔伯特，GJ戴维斯，H. Brumer，片段生物化学杂志2011 ，436，567–580）。在本研究中，结合了NMR光谱技术（包括饱和转移差异（STD）和转移NOE（TR-NOE）光谱）揭示了Cj Xyl31A活性位点变体与木葡聚糖六糖和七糖之间的广泛相互作用。数据具体表明，该酶在阳性酶亚位点识别底物和产物的整个纤维-四糖基骨架，并与内部α-（1→6）连接的木糖基内部侧链进一步显着相互作用。这样，本分析为Cj
• Kato, Yoji; Matsuda, Kazuo, Agricultural and Biological Chemistry, 1980, vol. 44, # 8, p. 1759 - 1766
  作者：Kato, Yoji、Matsuda, Kazuo

  DOI：——

  日期：——