4-甲基-7-[(4-O-BETA-D-吡喃木糖基-BETA-D-吡喃木糖基)氧基]-2H-1-苯并吡喃-2-酮 | 158962-91-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 4-甲基-7-[(4-O-BETA-D-吡喃木糖基-BETA-D-吡喃木糖基)氧基]-2H-1-苯并吡喃-2-酮
• 英文名称: 4-methylumbelliferyl-β-D-xylobioside
• 英文别名: 4-Methylumbelliferyl xylobiose；7-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-methylchromen-2-one
• CAS: 158962-91-5
• 化学式: C₂₀H₂₄O₁₁
• 分子量: 440.404
• InChiKey: OAEJNHLLPXDPCN-WZZSYRLHSA-N

物化性质

• 熔点：
  >200 °C (decomp)
• 沸点：
  739.9±60.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  164
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-甲基-7-[(4-O-BETA-D-吡喃木糖基-BETA-D-吡喃木糖基)氧基]-2H-1-苯并吡喃-2-酮 在 endo-1,4-β-D-xylanase from Sporotrichum thermophile 作用下， 以 acidic aq. solution 为溶剂， 反应 4.0h， 生成 D-(+)-xylobiose 、 羟甲香豆素
  参考文献：
  名称：

  Biochemical and catalytic properties of an endoxylanase purified from the culture filtrate of Sporotrichum thermophile

  摘要：

  An endo-beta-1,4-xylanase (1,4-beta-D-xylan xylanoxydrolase, EC 3.2.1.8) present in culture filtrates of Sporotrichum thermophile ATCC 34628 was purified to homogeneity by Q-Sepharose Lind Sephacryl S-200 column chromatographies. The enzyme has a molecular mass of 25,000 Da, an isoelectric point of 6.7, and is optimally active at pH 5 and at 70 degreesC. Thin-layer chromatography (TLC) analysis showed that endo-xylanase liberates mainly xylose (Xyl) and xylobiose (Xyl,) from beechwood 4-O-methyl-D-glucuronoxylan, O-acetyl-4-O-methylglucuronoxylan and rhodymenan (a beta-(1-->4)-beta(1-->3)-xylan). Also, the enzyme releases an acidic xylo-oligosaccharide from 4-O-methyl-D-glucuronoxylan, and an isomeric xylotetraose and an isomeric xylopentaose from rhodymenan. Analysis of reaction mixtures by high performance liquid chromatography (HPLC) revealed that the enzyme cleaves preferentially the internal glycosidic bonds of xylooligosaccharides, [1-H-3]-xylooligosaccharides and xylan. The enzyme also hydrolyses the 4-methylumbelliferyl glycosides of beta-xylobiose and beta-xylotriose at the second glycosidic bond adjacent to the aglycon. The endoxylanase is not active on pNPX and pNPC. The enzyme mediates a decrease in the viscosity of xylan associated with a release of only small amounts of reducing sugar. The enzyme is irreversibly inhibited by series of omega-epoxyalkyl glycosides of D-Xylopyranose. The results suggest that the endoxylanase from S. thermophile has catalytic properties similar to the enzymes belonging to family 11. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00291-x
• 作为产物：
  描述：

  4-methylumbelliferyl 2,3-di-O-benzoyl-β-D-xylopyranoside 在 氟磺酸甲酯 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 4-甲基-7-[(4-O-BETA-D-吡喃木糖基-BETA-D-吡喃木糖基)氧基]-2H-1-苯并吡喃-2-酮
  参考文献：
  名称：

  Chemo-enzymatic synthesis of 4-methylumbelliferyl β-(1→4)-d-xylooligosides: new substrates for β-d-xylanase assays

  摘要：

  利用曲霉属（Aspergillus sp.）的δ-D-木糖苷酶催化的转糖基化作用，合成了一组具有共同结构[δ-D-Xyl-(1â4)]2â5-δ-D-Xyl-MU的4-甲基伞形酮（MU）δ-1â4-D-木寡糖苷。以受保护的 MU δ-D-木吡喃糖苷与乙基 2,3,4-三-O-乙酰基-1-硫代-δ-D-木吡喃糖苷缩合合成的 MU xylobioside 为底物，用曲霉属的δ-D-木糖苷酶进行转糖基化，生成更高级的 MU xylooligosides。通过 1H 和 13C NMR 光谱以及电喷雾串联质谱法确定了所获得的低聚糖的结构。合成的 MU δ²-D-xylooligosides 被测试为黑曲霉 GH-10 家族 δ²-D-Xylanase 和毛霉 GH-11 家族 δ²-D-Xylanase I 的荧光底物。这两种木聚糖酶都能从 MU xylobioside 和相应的三苷中释放出琼脂酮。当底物的d.p.为4和5时，酶表现出内溶活性，主要分裂出MU、MUX和MUX2。

  DOI：

  10.1039/b409583a

文献信息

• An alternative approach for the synthesis of fluorogenic substrates of endo-β-(1→4)-xylanases and some applications
  作者：Mária Vršanská、Wim Nerinckx、Marc Claeyssens、Peter Biely

  DOI：10.1016/j.carres.2007.11.011

  日期：2008.2

  Fluorogenic substrates of endo-beta-(1-->4)-xylanases (EXs), 4-methylumbelliferyl beta-glycosides of xylobiose and xylotriose were synthesized from fully acetylated oligosaccharides using the alpha-trichloroacetimidate procedure. A commercially available syrup containing xylose and xylo-oligosaccharides was used as the starting material. Both fluorogenic glycosides were found to be suitable substrates

  使用α-三氯乙酰亚氨酸酯方法从完全乙酰化的寡糖合成β-内酯（1-> 4）-木聚糖酶（EXs），木糖和木三糖的4-甲基伞形酮基β-糖苷的荧光底物。含有木糖和木糖寡糖的市售糖浆用作原料。发现这两种荧光苷都是EX的合适底物，特别是用于电泳凝胶中酶的敏感检测以及它们在茄科所有番茄，马铃薯和茄子等植物子实体的部分上的原位定位。
• Syntheses of 4-Methylumbelliferyl-β-<scp>D</scp>-Xylobioside and 5-Bromo-3-Indolyl-β-<scp>D</scp>-Xylobioside for Sensitive Detection of Xylanase Activity on Agar Plates
  作者：Satoshi KANEKO、Motomitsu KITAOKA、Atsushi KUNO、Kiyoshi HAYASHI

  DOI：10.1271/bbb.64.741

  日期：2000.1

  4-Methylumbelliferyl-β-D-xylobioside (MU-X2) and 5-bromo-3-indolyl-β-D-xylobioside (BI-X2) were synthesized as substrates for the detection of xylanase activity on agar plates. A family F/10 xylanase from Streptomyces olivaceoviridis E-86 (FXYN) was able to be more sensitively detected than RBB-xylan by using MU-X2 as a substrate. A mutant xylanase E128H/FXYN having only 1/1000 of the activity of FXYN was also able to be detected on the MU-X2 plate but was not detected on the RBB-xylan plate. A family G/11 xylanase from Streptomyces lividans 66 (Xyn B) was not detected on the MU-X2 plate, but it was able to be detected on the RBB-xylan plate, suggesting that the MU-X2 substrate is specific to family F/10 xylanases. However, none of the xylanases were detected effectively by using BI-X2 as a substrate.

  4-甲基伞形酮-β-D-木二糖苷（MU-X2）和5-溴-3-吲哚基-β-D-木二糖苷（BI-X2）被合成为琼脂板检测木聚糖酶活性的底物。来自链霉菌属橄榄绿链霉菌E-86（FXYN）的F/10家族木聚糖酶使用MU-X2作为底物时比RBB-木聚糖更敏感地被检测到。仅有FXYN活性1/1000的突变木聚糖酶E128H/FXYN也能在MU-X2板上被检测到，但在RBB-木聚糖板上未被检测到。来自链霉菌属暗青链霉菌66（Xyn B）的G/11家族木聚糖酶未能在MU-X2板上被检测到，但它能在RBB-木聚糖板上被检测到，表明MU-X2底物对F/10家族木聚糖酶具有特异性。然而，没有任何木聚糖酶能通过使用BI-X2作为底物有效检测到。
• Biochemical and catalytic properties of an endoxylanase purified from the culture filtrate of Sporotrichum thermophile
  作者：Petros Katapodis、Maria Vršanská、Dimitris Kekos、Wim Nerinckx、Peter Biely、Marc Claeyssens、Basil J Macris、Paul Christakopoulos

  DOI：10.1016/s0008-6215(03)00291-x

  日期：2003.9

  An endo-beta-1,4-xylanase (1,4-beta-D-xylan xylanoxydrolase, EC 3.2.1.8) present in culture filtrates of Sporotrichum thermophile ATCC 34628 was purified to homogeneity by Q-Sepharose Lind Sephacryl S-200 column chromatographies. The enzyme has a molecular mass of 25,000 Da, an isoelectric point of 6.7, and is optimally active at pH 5 and at 70 degreesC. Thin-layer chromatography (TLC) analysis showed that endo-xylanase liberates mainly xylose (Xyl) and xylobiose (Xyl,) from beechwood 4-O-methyl-D-glucuronoxylan, O-acetyl-4-O-methylglucuronoxylan and rhodymenan (a beta-(1-->4)-beta(1-->3)-xylan). Also, the enzyme releases an acidic xylo-oligosaccharide from 4-O-methyl-D-glucuronoxylan, and an isomeric xylotetraose and an isomeric xylopentaose from rhodymenan. Analysis of reaction mixtures by high performance liquid chromatography (HPLC) revealed that the enzyme cleaves preferentially the internal glycosidic bonds of xylooligosaccharides, [1-H-3]-xylooligosaccharides and xylan. The enzyme also hydrolyses the 4-methylumbelliferyl glycosides of beta-xylobiose and beta-xylotriose at the second glycosidic bond adjacent to the aglycon. The endoxylanase is not active on pNPX and pNPC. The enzyme mediates a decrease in the viscosity of xylan associated with a release of only small amounts of reducing sugar. The enzyme is irreversibly inhibited by series of omega-epoxyalkyl glycosides of D-Xylopyranose. The results suggest that the endoxylanase from S. thermophile has catalytic properties similar to the enzymes belonging to family 11. (C) 2003 Elsevier Ltd. All rights reserved.
• Chemo-enzymatic synthesis of 4-methylumbelliferyl β-(1→4)-<scp>d</scp>-xylooligosides: new substrates for β-<scp>d</scp>-xylanase assays
  作者：Elena V. Eneyskaya、Dina R. Ivanen、Konstantin A. Shabalin、Anna A. Kulminskaya、Leon V. Backinowsky、Harry Brumer III、Kirill N. Neustroev

  DOI：10.1039/b409583a

  日期：——

  Transglycosylation catalyzed by a β-D-xylosidase from Aspergillus sp. was used to synthesize a set of 4-methylumbelliferyl (MU) β-1→4-D-xylooligosides having the common structure [β-D-Xyl-(1→4)]2–5-β-D-Xyl-MU. MU xylobioside synthesized chemically by the condensation of protected MU β-D-xylopyranoside with ethyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside was used as a substrate for transglycosylation with the β-D-xylosidase from Aspergillus sp. to produce higher MU xylooligosides. The structures of oligosaccharides obtained were established by 1H and 13C NMR spectroscopy and electrospray tandem mass spectrometry. MU β-D-xylooligosides synthesized were tested as fluorogenic substrates for the GH-10 family β-D-xylanase from Aspergillus orizae and the GH-11 family β-D-xylanase I from Trichoderma reesei. Both xylanases released the aglycone from MU xylobioside and the corresponding trioside. With substrates having d.p. 4 and 5, the enzymes manifested endolytic activities, splitting off MU, MUX, and MUX2 primarily.

  利用曲霉属（Aspergillus sp.）的δ-D-木糖苷酶催化的转糖基化作用，合成了一组具有共同结构[δ-D-Xyl-(1â4)]2â5-δ-D-Xyl-MU的4-甲基伞形酮（MU）δ-1â4-D-木寡糖苷。以受保护的 MU δ-D-木吡喃糖苷与乙基 2,3,4-三-O-乙酰基-1-硫代-δ-D-木吡喃糖苷缩合合成的 MU xylobioside 为底物，用曲霉属的δ-D-木糖苷酶进行转糖基化，生成更高级的 MU xylooligosides。通过 1H 和 13C NMR 光谱以及电喷雾串联质谱法确定了所获得的低聚糖的结构。合成的 MU δ²-D-xylooligosides 被测试为黑曲霉 GH-10 家族 δ²-D-Xylanase 和毛霉 GH-11 家族 δ²-D-Xylanase I 的荧光底物。这两种木聚糖酶都能从 MU xylobioside 和相应的三苷中释放出琼脂酮。当底物的d.p.为4和5时，酶表现出内溶活性，主要分裂出MU、MUX和MUX2。