o-nitrophenyl β-D-galactopyranosyl<1->3>-β-D-galactopyranoside | 139639-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: o-nitrophenyl β-D-galactopyranosyl<1->3>-β-D-galactopyranoside
• 英文别名: 2-nitrophenyl β-D-galactopyranosyl-[1->3]-β-D-galactopyranoside；o-nitrophenyl 3-O-(β-D-galactopyranosyl)-β-D-galactopyranoside；Gal(b1-3)Gal(b)-O-Ph(2-NO2)；(2S,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(2-nitrophenoxy)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 139639-82-0
• 化学式: C₁₈H₂₅NO₁₃
• 分子量: 463.395
• InChiKey: QOJLWWAFAQOCRG-UFNIBABYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  224
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  尾-D-Galactoside,2-nitrophenyl(9CI) 在 β-glycosidase from Thermus thermophilus overexpressed into E. coli cells (BL 21pETbg8) 、 phosphate puffer 作用下， 反应 1.5h， 生成 o-nitrophenyl β-D-galactopyranosyl<1->3>-β-D-galactopyranoside 、 o-nitrophenyl β-D-galactopyranosyl<1->6>-β-D-galactopyranoside
  参考文献：
  名称：

  嗜热栖热菌 β-糖苷酶的转移酶活性：特异性和限制——在 β-[1→3]-二糖合成中的应用

  摘要：

  本文的目的是测试嗜热栖热菌的 β-糖苷酶在硝基苯基糖苷作为供体和其他单糖作为受体的情况下催化转糖基化反应的能力。我们的结果表明，该酶能够与硝基苯基半乳糖苷、β-葡萄糖苷和β-岩藻糖苷一起诱导此类反应。对于前两个供体，供体的自动缩合（因此也充当受体）比与其他受体的转糖基化作用更快。此外，由于反应的区域选择性主要是 β-[13] 型，因此合成 2-硝基苯基-β-D-吡喃半乳糖基-[13]-β-D-吡喃半乳糖苷和 2-硝基苯基-β-D-吡喃葡萄糖苷-[13]-β-D-吡喃葡萄糖苷。相反，在对硝基苯基岩藻糖苷存在下，

  DOI：

  10.1002/(sici)1099-0690(199904)1999:4<757::aid-ejoc757>3.0.co;2-3

文献信息

• Transferase Activity of a β-Glycosidase fromThermus thermophilus: Specificities and Limits – Application to the Synthesis of β-[1→3]-Disaccharides
  作者：Violaine Chiffoleau-Giraud、Petra Spangenberg、Michel Dion、Claude Rabiller

  DOI：10.1002/(sici)1099-0690(199904)1999:4<757::aid-ejoc757>3.0.co;2-3

  日期：1999.4

  reactions is mainly of the β-[13] type, good yields are obtained for the synthesis of 2-nitrophenyl-β-D-galactopyranosyl-[13]-β-D-galactopyranoside and 2-nitrophenyl-β-D-glucopyranosyl-[13]-β-D-glucopyranoside. Conversely, in the presence of p-nitrophenylfucoside, the autocondensation is very limited, and with methyl-α-D-galactoside as an acceptor, the regioselectivity is mainly of the β-[16]-type resulting

  本文的目的是测试嗜热栖热菌的 β-糖苷酶在硝基苯基糖苷作为供体和其他单糖作为受体的情况下催化转糖基化反应的能力。我们的结果表明，该酶能够与硝基苯基半乳糖苷、β-葡萄糖苷和β-岩藻糖苷一起诱导此类反应。对于前两个供体，供体的自动缩合（因此也充当受体）比与其他受体的转糖基化作用更快。此外，由于反应的区域选择性主要是 β-[13] 型，因此合成 2-硝基苯基-β-D-吡喃半乳糖基-[13]-β-D-吡喃半乳糖苷和 2-硝基苯基-β-D-吡喃葡萄糖苷-[13]-β-D-吡喃葡萄糖苷。相反，在对硝基苯基岩藻糖苷存在下，
• Probing the transferase activity of glycosidases by means of in situ NMR spectroscopy
  作者：P Spangenberg、V Chiffoleau-Giraud、C André、M Dion、C Rabiller

  DOI：10.1016/s0957-4166(99)00297-9

  日期：1999.7

  This paper describes the conditions in which in situ NMR spectroscopy is a suitable technique to use when following the course of enzymatic transglycosylation reactions. Using this methodology, the reactions must be carried out in D2O. Our experiments indicate that the rate of the transglycosylation reaction is reduced in this solvent while the rate of the hydrolysis of the disaccharides produced is enhanced depending on the nature of the anomeric substituent. However, this undesirable effect is generally weak because the rates of the transglycosylation reactions are always faster than the rates of the hydrolysis whatever the solvent. The great advantage of NMR spectroscopy lies in its potential to detect, in a single experiment, all the components of the reaction without any disturbance of the reaction medium. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Galactosylation and glucosylation by use of β-galactosidase
  作者：Bernd Sauerbrei、Joachim Thiem

  DOI：10.1016/0040-4039(92)88050-f

  日期：1992.1

  The transglycosylation activity of beta-galactosidase derived from Aspergillus oryzae and Escherichia coli, respectively, was examined in reaction systems containing up to 50% acetonitrile. Starting with ortho-nitrophenyl beta-galactoside (1), which functions both as donor and as acceptor, beta-Gal(1-6)beta-Gal-PhNO2-omicron (2) and beta-Gal(1-3)beta-Gal-PhNO2-omicron (3) were obtained. Under similar conditions the enzyme from A. oryzae converts para-nitrophenyl beta-glucoside (5) to beta-Glc(1-2)beta-Glc-PhNO2-p (6) and alpha-Glc(1-4)beta-Glc-PhNO2-p (7). Incubation of 1 and L-serine in the presence of the A. oryzae beta-galactosidase leads to beta-Gal-L-Ser (4).
• Enzymatic syntheses and selective hydrolysis of O-β-d-galactopyranosides using a marine mollusc β-galactosidase
  作者：Assunta Giordano、Annabella Tramice、Giuseppina Andreotti、Ernesto Mollo、Antonio Trincone

  DOI：10.1016/j.bmcl.2004.10.016

  日期：2005.1

  The use of crude extract of the hepatopancreas of Aplysia fasciata, a large mollusc belonging to the order Anaspidea containing a beta-galactosidase activity, was reported for the synthesis of different galactosides. Good yields with polar acceptors and the uncommon beta-1-3 selectivity in the transgalactosylation reactions with most of the acceptors were observed. A beta-1-2 selectivity in the hydrolytic conditions was also observed and discussed. (C) 2004 Elsevier Ltd. All rights reserved.