[α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-α,β-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-α,β-D-glucopyranose
• 英文别名: α-D-xylopyranosyl-(1->6)-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-β-D-glucopyranose；α-1,6-xylopyranose-β-1,4-glucopyranose-(β-1,2-galactopyranose-α-1,6-xylopyranose)-β-1,4-glucopyranose-(β-1,2-galactopyranose-α-1,6-xylopyranose)-β-1,4-glucopyranose-glucopyranose；[(Xylα1-6)Glcβ1-4][{(Galβ1-2)Xylα1-6}Glcβ1-4]2Glc；Xyl(a1-6)Glc(b1-4)[Gal(b1-2)Xyl(a1-6)]Glc(b1-4)[Gal(b1-2)Xyl(a1-6)]Glc(b1-4)Glc；(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5R)-2-[[(2R,3S,4R,5R,6S)-3-[(2S,3R,4R,5S,6R)-6-[[(2R,3R,4S,5R)-4,5-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4-dihydroxy-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-4,5-dihydroxy-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]-4,5-dihydroxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₅₁H₈₆O₄₃
• 分子量: 1387.22
• InChiKey: GSCHIGXDTVYEEM-ULLBEXLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -17.3
• 重原子数：
  94
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  683
• 氢给体数：
  26
• 氢受体数：
  43

反应信息

• 作为反应物：
  描述：

  [α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-α,β-D-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49%的产率得到α-D-xylopyranosyl-(1->6)-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-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：

  [(2,3,4-tri-O-acetyl-α-D-xylopyranosyl)-(1->6)]-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-D-xylopyranosyl)-(1->6)]-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->2)-(3,4-di-O-acetyl-α-D-xylopyranosyl)-(1->6)]-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-α,β-D-glucopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 [α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)-α-D-xylopyranosyl-(1->6)]-β-D-glucopyranosyl-(1->4)-α,β-D-glucopyranose
  参考文献：
  名称：

  Chemo-enzymatic synthesis of xylogluco-oligosaccharides and their interactions with cellulose

  摘要：

  A novel class of complex oligosaccharides with a backbone made of twelve beta-(1 -> 4)-D-glucosyl units that may be regularly substituted on their primary position with alpha-D-xylosyl or beta-D-(1 -> 2)-galactosyl-alpha-D-xylosyl residues were readily synthesized using enzymatic hydrolysis of the plant polysaccharide xyloglucan (XG), followed by chemical modifications of the well-defined oligosaccharides and their enzymatic coupling catalyzed by the Cel7B E197A glycosynthase from Humicola insolens. These complex oligosaccharides proved useful for a better understanding of the effects of structural variation of xyloglucan on interactions with bacterial microcrystalline cellulose (BMCC). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2011.11.085

文献信息

• 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。
• 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
  作者：Atsushi Kobayashi、Tomonari Tanaka、Kazuhito Watanabe、Masaki Ishihara、Masato Noguchi、Hirofumi Okada、Yasushi Morikawa、Shin-ichiro Shoda

  DOI：10.1016/j.bmcl.2010.04.122

  日期：2010.6

  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.
• One-step conversion of unprotected sugars to β-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution
  作者：Tomonari Tanaka、Hikaru Nagai、Masato Noguchi、Atsushi Kobayashi、Shin-ichiro Shoda

  DOI：10.1039/b905761g

  日期：——

  Various β-glycosyl azides have been synthesized directly in water by the reaction of unprotected sugars and sodium azide mediated by 2-chloro-1,3-dimethylimidazolinium chloride (DMC).

  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。
• Chemo-enzymatic synthesis of xylogluco-oligosaccharides and their interactions with cellulose
  作者：Marie Lopez、Sébastien Fort、Hervé Bizot、Alain Buléon、Hugues Driguez

  DOI：10.1016/j.carbpol.2011.11.085

  日期：2012.3

  A novel class of complex oligosaccharides with a backbone made of twelve beta-(1 -> 4)-D-glucosyl units that may be regularly substituted on their primary position with alpha-D-xylosyl or beta-D-(1 -> 2)-galactosyl-alpha-D-xylosyl residues were readily synthesized using enzymatic hydrolysis of the plant polysaccharide xyloglucan (XG), followed by chemical modifications of the well-defined oligosaccharides and their enzymatic coupling catalyzed by the Cel7B E197A glycosynthase from Humicola insolens. These complex oligosaccharides proved useful for a better understanding of the effects of structural variation of xyloglucan on interactions with bacterial microcrystalline cellulose (BMCC). (C) 2011 Elsevier Ltd. All rights reserved.