4-nitrophenyl (α-D-galactopyranosyl)-(1->2)-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl (α-D-galactopyranosyl)-(1->2)-α-D-galactopyranoside
• 英文别名: α-D-Galp-(1->2)-α-D-Galp-O-p-NO2Ph；Gal(a1-2)Gal(a)-O-Ph(4-NO2)；(2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₈H₂₅NO₁₃
• 分子量: 463.395
• InChiKey: ZGWCYKZKLZNQQX-XBOLJQQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 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：

  4-硝基苯基-α-D-吡喃半乳糖苷 在 α-galactosidase 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以28.6 mg的产率得到4-nitrophenyl (α-D-galactopyranosyl)-(1->2)-α-D-galactopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of Galα1-3Gal, Galα1-3Galβ1-4GlcNAc and their PEG-conjugates.

  摘要：

  Gal alpha 1-3Gal-pNP was prepared enzymatically from Gal-pNP using alpha-galactosidase from coffee beans. PEG was attached after the reduction of nitro group into amino group to give Gal alpha 1-3Gal-PEG conjugate. After removing the pNP group in Gal alpha 1-3Gal-pNP, the obtained disaccharide was used for the synthesis of Gal alpha 1-3Gal beta 1-4GlcNAc and corresponding trisaccharide-PEG conjugate. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00017-6

文献信息

• α-Galactobiosyl units: thermodynamics and kinetics of their formation by transglycosylations catalysed by the GH36 α-galactosidase from Thermotoga maritima
  作者：Anna S. Borisova、Dina R. Ivanen、Kirill S. Bobrov、Elena V. Eneyskaya、Georgy N. Rychkov、Mats Sandgren、Anna A. Kulminskaya、Michael L. Sinnott、Konstantin A. Shabalin

  DOI：10.1016/j.carres.2014.11.003

  日期：2015.1

  a limiting factor for application of the enzyme in the directed synthesis of oligogalactosides. However, this property can be used as a convenient tool in studies of thermodynamics of a glycosidic bond. Here, a novel approach to energy difference estimation is suggested. Both transglycosylation and hydrolysis of three types of galactosidic linkages were investigated using total kinetics of formation

  来自滨海嗜热菌（TmGal36A）的α-半乳糖苷酶的广泛区域选择性是该酶在寡半乳糖苷的定向合成中应用的限制因素。但是，该性质可以用作研究糖苷键热力学的方便工具。在此，提出了一种新的能量差估计方法。使用由海藻T.36（一种保留性的外泌作用糖苷水解酶）的单体糖苷水解酶家族36α-半乳糖苷酶催化的pNP-半乳糖苷的形成和水解的总动力学，研究了三种类型的半乳糖苷键的转糖基化和水解。我们估计了1,2-和1,3-键之间的过渡态自由能差（DeltaDeltaG（double dagger）0值等于5.34 +/- 0.85 kJ / mol）和1,6-键和1，之间 在由TmGal36A催化的反应过程中，pNP-半乳糖苷中有3个键（DeltaDeltaG（双匕首）0 = 1.46 +/- 0.23 kJ / mol）。利用自由能差形成和水解糖苷键（DeltaDeltaG（双匕首）F-DeltaDeltaG（双匕首）H），我们发现1
• α-Galactosyl fluoride in transfer reactions mediated by the green coffee beans α-galactosidase in ice
  作者：Petra Spangenberg、Corinne André、Virginie Langlois、Michel Dion、Claude Rabiller

  DOI：10.1016/s0008-6215(01)00309-3

  日期：2002.2

  We show that the yields in saccharide synthesis by tranglycosylation with alpha-galactosidase from green coffee beans can be greatly enhanced when working in ice. Thus, methyl alpha-D-galactopyranosyl-(1-->3)-alpha-D-galactopyranoside (3a) produced by reaction of alpha-D-galactopyranosyl fluoride 1 with methyl alpha-D-galactopyranoside (2) is obtained with 51% yield in ice while only 29% is synthesized at 37 degreesC. This result, already previously found by others with proteases and by us with a P-galactosidase appears to be a general property of hydrolases. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Chemoenzymatic synthesis of Galα1-3Gal, Galα1-3Galβ1-4GlcNAc and their PEG-conjugates.
  作者：Ichiro Matsuo、Hiroshi Fujimoto、Megumi Isomura、Katsumi Ajisaka

  DOI：10.1016/s0960-894x(97)00017-6

  日期：1997.2

  Gal alpha 1-3Gal-pNP was prepared enzymatically from Gal-pNP using alpha-galactosidase from coffee beans. PEG was attached after the reduction of nitro group into amino group to give Gal alpha 1-3Gal-PEG conjugate. After removing the pNP group in Gal alpha 1-3Gal-pNP, the obtained disaccharide was used for the synthesis of Gal alpha 1-3Gal beta 1-4GlcNAc and corresponding trisaccharide-PEG conjugate. (C) 1997, Elsevier Science Ltd.