(4-O-Methyl-α-D-glucopyranosyluronic acid)-(1->2)-β-D-xylopyranosyl-(1->2)-D-xylopyranose | 19234-63-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-O-Methyl-α-D-glucopyranosyluronic acid)-(1->2)-β-D-xylopyranosyl-(1->2)-D-xylopyranose
• 英文别名: 2²-4-O-Methyl-α-D-glucuronopyranosylxylobiose；2'-O-(4-O-methyl-α-D-glucosyluronic acid)xylobiose；aldotriouronic acid；Aldotrio-uronsaeure-O--4-D-xylopyranose；Aldotriuronsaeure；Aldotrio-uronsaeure-O-[O-mono-(O-methyl-4α-D-glucuronopyranosyl)-2β-D-xylopyranosyl]-4-D-xylopyranose；GlcA4Me(a1-2)Xyl(b1-4)Xyl；(2S,3S,4R,5R,6S)-6-[(2S,3R,4S,5R)-4,5-dihydroxy-2-[(3R,4R,5R)-4,5,6-trihydroxyoxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-3-methoxyoxane-2-carboxylic acid
• CAS: 19234-63-0
• 化学式: C₁₇H₂₈O₁₅
• 分子量: 472.4
• InChiKey: XZGRJCXNJVJWKJ-QPLJXEPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  234
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (4-O-Methyl-α-D-glucopyranosyluronic acid)-(1->2)-β-D-xylopyranosyl-(1->2)-D-xylopyranose 在 α-glucuronidase GH67 、 xylanase XYN IV from trichoderma reesei 作用下， 以 aq. buffer 为溶剂， 生成 D-吡喃木糖
  参考文献：
  名称：

  Xylanase XYN IV fromTrichoderma reeseishowing exo- and endo-xylanase activity

  摘要：

  A minor xylanase, named XYN IV, was purified from the cellulolytic system of the fungus Trichoderma reesei Rut C30. The enzyme was discovered on the basis of its ability to attack aldotetraohexenuronic acid (HexA‐2Xyl‐4Xyl‐4Xyl, HexA3Xyl3), releasing the reducing‐end xylose residue. XYN IV exhibited catalytic properties incompatible with previously described endo‐β‐1,4‐xylanases of this fungus, XYN I, XYN II and XYN III, and the xylan‐hydrolyzing endo‐β‐1,4‐glucanase EG I. XYN IV was able to degrade several different β‐1,4‐xylans, but was inactive on β‐1,4‐mannans and β‐1,4‐glucans. It showed both exo‐and endo‐xylanase activity. Rhodymenan, a linear soluble β‐1,3‐β‐1,4‐xylan, was as the best substrate. Linear xylooligosaccharides were attacked exclusively at the first glycosidic linkage from the reducing end. The gene xyn4, encoding XYN IV, was also isolated. It showed clear homology with xylanases classified in glycoside hydrolase family 30, which also includes glucanases and mannanases. The xyn4 gene was expressed slightly when grown on xylose and xylitol, clearly on arabinose, arabitol, sophorose, xylobiose, xylan and cellulose, but not on glucose or sorbitol, resembling induction of other xylanolytic enzymes from T. reesei. A recombinant enzyme prepared in a Pichia pastoris expression system exhibited identical catalytic properties to the enzyme isolated from the T. reesei culture medium. The physiological role of this unique enzyme remains unknown, but it may involve liberation of xylose from the reducing end of branched oligosaccharides that are resistant toward β‐xylosidase and other types of endoxylanases. In terms of its catalytic properties, XYN IV differs from bacterial GH family 30 glucuronoxylanases that recognize 4‐O‐methyl‐d‐glucuronic acid (MeGlcA) substituents as substrate specificity determinants.

  DOI：

  10.1111/febs.12069
• 作为产物：
  描述：

  在 palladium dihydroxide 吡啶 、 重铬酸吡啶 、 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 水 、 氢气 、 sodium methylate 、 溶剂黄146 、 DMTST 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0 ℃ 、689.49 kPa 条件下， 反应 36.0h， 生成 (4-O-Methyl-α-D-glucopyranosyluronic acid)-(1->2)-β-D-xylopyranosyl-(1->2)-D-xylopyranose
  参考文献：
  名称：

  在木材和纸浆中发现的含糖醛酸木聚糖的合成

  摘要：

  含两个糖醛酸 三糖，（4-脱氧β-大号-苏式-己-4- enopyranosyluronic酸） -和（4- ö甲基α- d -gluropyranosyluronic酸） - （1→2）-β- d -xylopyranosyl-（1 →4）-从纸浆中合成酶水解产物中发现的D-木吡喃糖。常见的二木糖苷2'-OH受体对甲氧基苯基[3,4- O-（2'，3'-二甲氧基丁烷-2'，3'-二基）-β- D-木吡喃糖基]-（1→4）-构建2，3-二-O-苯甲酰基-β - D-吡喃吡喃糖苷，并与在4-位不同取代的两个葡萄糖醛酸硫代糖苷供体，O-甲基和O-mesyl分别给出 三糖。DMTST作为中的启动子乙醚仅以高收率得到α-连接产物。然后用DBU处理4″ -O-甲磺酰基三糖，得到不饱和的α，β糖醛酸衍生物。受体中引入的保护模式可以继续合成更大的寡糖。除去丁二酮缩醛产生3'，4'-受体，并且对甲氧基苯基

  DOI：

  10.1039/b009670a

文献信息

• 2D-n.m.r. analysis of the structure of an aldotriouronic acid obtained from birch wood
  作者：Friedrich Cavagna、Hans Deger、Jürgen Puls

  DOI：10.1016/0008-6215(84)85293-3

  日期：1984.7

  primary structure of the trisaccharide 2′- O -(4- O -methyl-α- d -glucosyluronic acid)xylobiose, which was obtained from birch wood, has been determined by n.m.r. spectroscopy, using homonuclear and heteronuclear, shift-correlated, two-dimensional techniques.

  摘要桦木中的三糖2'-O-（4-O-甲基-α-d-葡萄糖基葡糖醛酸）木糖的一级结构已通过核磁共振波谱法测定，采用同核和异核，移位相关，二维技术。
• Xylanase XYN IV from<i>Trichoderma reesei</i>showing exo- and endo-xylanase activity
  作者：Maija Tenkanen、Mária Vršanská、Matti Siika-aho、Dominic W. Wong、Vladimír Puchart、Merja Penttilä、Markku Saloheimo、Peter Biely

  DOI：10.1111/febs.12069

  日期：2013.1

  A minor xylanase, named XYN IV, was purified from the cellulolytic system of the fungus Trichoderma reesei Rut C30. The enzyme was discovered on the basis of its ability to attack aldotetraohexenuronic acid (HexA‐2Xyl‐4Xyl‐4Xyl, HexA3Xyl3), releasing the reducing‐end xylose residue. XYN IV exhibited catalytic properties incompatible with previously described endo‐β‐1,4‐xylanases of this fungus, XYN I, XYN II and XYN III, and the xylan‐hydrolyzing endo‐β‐1,4‐glucanase EG I. XYN IV was able to degrade several different β‐1,4‐xylans, but was inactive on β‐1,4‐mannans and β‐1,4‐glucans. It showed both exo‐and endo‐xylanase activity. Rhodymenan, a linear soluble β‐1,3‐β‐1,4‐xylan, was as the best substrate. Linear xylooligosaccharides were attacked exclusively at the first glycosidic linkage from the reducing end. The gene xyn4, encoding XYN IV, was also isolated. It showed clear homology with xylanases classified in glycoside hydrolase family 30, which also includes glucanases and mannanases. The xyn4 gene was expressed slightly when grown on xylose and xylitol, clearly on arabinose, arabitol, sophorose, xylobiose, xylan and cellulose, but not on glucose or sorbitol, resembling induction of other xylanolytic enzymes from T. reesei. A recombinant enzyme prepared in a Pichia pastoris expression system exhibited identical catalytic properties to the enzyme isolated from the T. reesei culture medium. The physiological role of this unique enzyme remains unknown, but it may involve liberation of xylose from the reducing end of branched oligosaccharides that are resistant toward β‐xylosidase and other types of endoxylanases. In terms of its catalytic properties, XYN IV differs from bacterial GH family 30 glucuronoxylanases that recognize 4‐O‐methyl‐d‐glucuronic acid (MeGlcA) substituents as substrate specificity determinants.
• Synthesis of uronic acid-containing xylans found in wood and pulp
  作者：Stefan Oscarson、Pär Svahnberg

  DOI：10.1039/b009670a

  日期：——

  with two glucuronate thioglycoside donors differently substituted in the 4-position, O-methyl and O-mesyl, respectively, to give trisaccharides. DMTST as promoter in diethyl ether gives exclusively the α-linked products in high yield. Treatment of the 4″-O-mesyl trisaccharide with DBU then gives the α,β-unsaturated uronic acid derivative. The protection pattern introduced in the acceptor allows continued

  含两个糖醛酸 三糖，（4-脱氧β-大号-苏式-己-4- enopyranosyluronic酸） -和（4- ö甲基α- d -gluropyranosyluronic酸） - （1→2）-β- d -xylopyranosyl-（1 →4）-从纸浆中合成酶水解产物中发现的D-木吡喃糖。常见的二木糖苷2'-OH受体对甲氧基苯基[3,4- O-（2'，3'-二甲氧基丁烷-2'，3'-二基）-β- D-木吡喃糖基]-（1→4）-构建2，3-二-O-苯甲酰基-β - D-吡喃吡喃糖苷，并与在4-位不同取代的两个葡萄糖醛酸硫代糖苷供体，O-甲基和O-mesyl分别给出 三糖。DMTST作为中的启动子乙醚仅以高收率得到α-连接产物。然后用DBU处理4″ -O-甲磺酰基三糖，得到不饱和的α，β糖醛酸衍生物。受体中引入的保护模式可以继续合成更大的寡糖。除去丁二酮缩醛产生3'，4'-受体，并且对甲氧基苯基