4-甲基伞形酮-Β-昆布二糖苷 | 172364-08-8

• 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-甲基伞形酮-Β-昆布二糖苷
• 英文名称: 4-methylumbelliferyl 3-O-β-D-glucopyranosyl-β-D-glucopyranoside
• 英文别名: 4-methylumbelliferyl β-laminarabioside；4-methylumbelliferyl β-D-laminaribioside；7-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methylchromen-2-one
• CAS: 172364-08-8
• 化学式: C₂₂H₂₈O₁₃
• 分子量: 500.457
• InChiKey: JNAWLDYZIIXRCJ-FIRLIKODSA-N

物化性质

• 沸点：
  847.8±65.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  205
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4-甲基伞形酮-Β-昆布二糖苷 在 β-1,3-1,4-D-glucanase from Rhodothermus marinus 作用下， 以 acetate buffer 为溶剂， 生成 羟甲香豆素
  参考文献：
  名称：

  Enzymatic synthesis of 4-methylumbelliferyl (1→3)-β-d-glucooligosaccharides—new substrates for β-1,3-1,4-d-glucanase

  摘要：

  The transglycosylation reactions catalyzed by beta-1,3-D-glucanases (laminaranases) were used to synthesize a number of 4-methylumbelliferyl (MeUmb) (1 --> 3)-beta-D-gluco-oligosaccharides having the common structure [beta-D-Glcp-(1 --> 3)](n)-beta-D-Glcp-MeUmb, where n = 1-5. The beta-1,3-D-glucanases used were purified from the culture liquid of Oerskovia sp. and from a homogenate of the marine mollusc Spisula sachalinensis. Laminaran and curdlan were used as (1 --> 3)-beta-D-glucan donor substrates, while MeUmb-beta-D-glucoside (MeUmbGlcp) was employed as a transglycosylation acceptor. Modification of [beta-D-Glcp-(1 --> 3)](2)-beta-D-Glcp-MeUmb (MeUmbG(3)) gives 4,6-O-benzylidene-D-glucopyranosyl or 4,6-O-ethylidene-D-glucopyranosyl groups at the non-reducing end of artificial oligosaccharides. The structures of all oligosaccharides obtained were solved by H-1 and C-13 NMR spectroscopy and electrospray tandem mass spectrometry. The synthetic oligosaccharides were shown to be substrates for a beta-1,3-1,4-D-glucanase from Rhodothermus marinus, which releases MeUmb from beta-di- and beta-triglucosides and from acetal-protected beta-triglucosides. When acting upon substrates with d.p. > 3, the enzyme exhibits an endolytic activity, primarily cleaving off MeUrnbGlcP and MeUmbG(2). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00199-x
• 作为产物：
  描述：

  羟甲香豆素 在 palladium on activated charcoal sodium hydroxide 、 4 A molecular sieve 、 D(+)-10-樟脑磺酸 、 氢气 、 sodium methylate 、 四丁基硫酸氢铵 、 溶剂黄146 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 110.75h， 生成 4-甲基伞形酮-Β-昆布二糖苷
  参考文献：
  名称：

  作为（1-> 3），（1-> 4）-β-D-葡聚糖4-葡聚糖水解酶的特定发色底物的4-甲基伞形基-β-D-葡聚糖寡糖的合成

  摘要：

  DOI：

  10.1016/0008-6215(95)00102-y

文献信息

• Glycosynthase-Catalysed syntheses at pH below neutrality
  作者：Antonio Trincone、Assunta Giordano、Giuseppe Perugino、Mosè Rossi、Marco Moracci

  DOI：10.1016/j.bmcl.2003.08.037

  日期：2003.11

  The use of the new glycosynthase Ta-beta-GlyE386G and of the already known Ss-beta-GlyE387G for the synthesis of interesting 4-methylumbelliferyl disaccharides and for the galactosylation of alpha- and beta-xylosides of 4-penten-1-ol is reported. The results show satisfactory yields of reaction in presence of low excesses of acceptors and demonstrated that the high activity of these enzymes at pH below neutrality is applicable in the transfer of glucose as well as of galactose from the preferred 2-NP-based donors. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of 4-methylumbelliferyl-β-d-glucan oligosaccharides as specific chromophoric substrates of (1 → 3),(1 → 4)-β-d-glucan 4-glucanohydrolases
  作者：Carles Malet、Josep Lluis Viladot、Ana Ochoa、Belen Gallégo、Carme Brosa、Antoni Planas

  DOI：10.1016/0008-6215(95)00102-y

  日期：1995.9
• Enzymatic synthesis of 4-methylumbelliferyl (1→3)-β-d-glucooligosaccharides—new substrates for β-1,3-1,4-d-glucanase
  作者：Rainer Borriss、Martin Krah、Harry Brumer、Maxim A. Kerzhner、Dina R. Ivanen、Elena V. Eneyskaya、Lyudmila A. Elyakova、Sergei M. Shishlyannikov、Konstantin A. Shabalin、Kirill N. Neustroev

  DOI：10.1016/s0008-6215(03)00199-x

  日期：2003.7

  The transglycosylation reactions catalyzed by beta-1,3-D-glucanases (laminaranases) were used to synthesize a number of 4-methylumbelliferyl (MeUmb) (1 --> 3)-beta-D-gluco-oligosaccharides having the common structure [beta-D-Glcp-(1 --> 3)](n)-beta-D-Glcp-MeUmb, where n = 1-5. The beta-1,3-D-glucanases used were purified from the culture liquid of Oerskovia sp. and from a homogenate of the marine mollusc Spisula sachalinensis. Laminaran and curdlan were used as (1 --> 3)-beta-D-glucan donor substrates, while MeUmb-beta-D-glucoside (MeUmbGlcp) was employed as a transglycosylation acceptor. Modification of [beta-D-Glcp-(1 --> 3)](2)-beta-D-Glcp-MeUmb (MeUmbG(3)) gives 4,6-O-benzylidene-D-glucopyranosyl or 4,6-O-ethylidene-D-glucopyranosyl groups at the non-reducing end of artificial oligosaccharides. The structures of all oligosaccharides obtained were solved by H-1 and C-13 NMR spectroscopy and electrospray tandem mass spectrometry. The synthetic oligosaccharides were shown to be substrates for a beta-1,3-1,4-D-glucanase from Rhodothermus marinus, which releases MeUmb from beta-di- and beta-triglucosides and from acetal-protected beta-triglucosides. When acting upon substrates with d.p. > 3, the enzyme exhibits an endolytic activity, primarily cleaving off MeUrnbGlcP and MeUmbG(2). (C) 2003 Elsevier Science Ltd. All rights reserved.