p-nitrophenyl 3-O-β-D-galactopyranosyl-β-D-galactopyranoside | 81573-30-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 3-O-β-D-galactopyranosyl-β-D-galactopyranoside
• 英文别名: p-nitrophenyl 3-O-(beta-D-galactopyranosyl)-beta-D-galactopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 81573-30-0
• 化学式: C₁₈H₂₅NO₁₃
• 分子量: 463.395
• InChiKey: LBTDRWMZFQVCAR-UFNIBABYSA-N

物化性质

• 沸点：
  814.5±65.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  乙酸酐 、 p-nitrophenyl 3-O-β-D-galactopyranosyl-β-D-galactopyranoside 在 吡啶 作用下， 以95%的产率得到p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of spacer-linked oligosaccharides for the preparation of neoglycoproteins

  摘要：

  In the present work, the combination of chemical and enzymatic methods to obtain neoglycoproteins is described. Three bovine serum albumin (BSA)-conjugates, BSA-[GalNAc alpha-], BSA-[Gal(beta 1-3)GalNAc(alpha-], and BSA-[Neu5Ac(alpha 2-3)Gal(beta 1-3)GalNAc(alpha-], were prepared, alpha GalNAc derivatives were galactosylated employing crude P-galactosidase from bovine testes. The use of oversaturated donor solutions (pNP beta Gal) enhanced the yields up to 60%. This method was verified using divalent structures as accepters, that rendered di- and tri-galactosylated products. Further treatment of the disaccharides with CMP-Neu5Ac and alpha 2-3 sialyltransferase from pork liver led to formation of trisaccharides. Finally, mono-, di-, and trisaccharides were coupled to BSA employing a thiolic group introduced into the protein for Michael addition to a maleinimide group in the spacer-ann of the saccharide components. The results were monitored by HPLC and MALDI-TOF. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00073-7
• 作为产物：
  描述：

  p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以75%的产率得到p-nitrophenyl 3-O-β-D-galactopyranosyl-β-D-galactopyranoside
  参考文献：
  名称：

  对硝基苯基3-O-β-d-吡喃半乳糖苷-β-d-吡喃半乳糖苷和对硝基苯基3-O-α-d-吡喃半乳糖苷-β-d-吡喃半乳糖苷

  摘要：

  摘要对硝基苯基2,4,6-三-O-乙酰基-β-d-吡喃半乳糖苷（2）与2,3,4,6-四-O-乙酰基-α-d的糖基化反应（氰化汞催化）在乙腈中的-半乳糖基吡喃糖基溴化物以几乎相等的比例提供α-（1→3）-和β-（1→3）连接的二糖七乙酸酯（分别为4和6）。对-硝基苯基2-O-苯甲酰基-4,6-O-亚苄基-β-d-吡喃半乳糖苷（3）的类似糖基化反应产生了β-（1→3）-和α-（1→3）-相连，以3：1的比例完全保护的二糖衍生物（分别为8和10）。4，6，8和10的结构由它们各自的1 Hn.mr光谱证明。4和6的O-脱乙酰基分别提供对-硝基苯基3- O-α-d-吡喃半乳糖基-β-d-吡喃半乳糖苷（5）和对-硝基苯基3- O-β-d-吡喃半乳糖基-β-d-半乳糖吡喃糖苷（7）。8和10的O-脱酰作用提供了二糖衍生物（9和11）。9和11的亚苄基的切割分别给出了二糖7和5。5，7，9和11的结构是通过13

  DOI：

  10.1016/s0008-6215(00)81003-4

文献信息

• Convenient enzymatic synthesis of a p-nitrophenyl oligosaccharide series of sialyl N-acetyllactosamine, sialyl Lex and relevant compounds
  作者：Xiaoxiong Zeng、Hirotaka Uzawa

  DOI：10.1016/j.carres.2005.08.019

  日期：2005.11

  From the beta-D-Gal-(1-->4)-beta-D-GlcNAc-OC6H4NO2-p (1) prepared by the transglycosylation of beta-galactosidase from Bacillus circulans, alpha-D-Neu5Ac-(2-->3)-beta-D-Gal-(1-->4)-beta-D-GlcNAc-OC6H4NO2-p (9) and alpha-D-Neu5Ac-(2-->6)-beta-D-Gal-(1-->4)-beta-D-GlcNAc-OC6H4NO2-p (10) were effectively synthesized with an equimolar ratio of CMP-Neu5Ac by recombinant rat alpha-(2-->3)-N-sialyltransferase

  从β-D-Gal-（1→4）-β-D-GlcNAc-OC6H4NO2-p（1）通过环回芽孢杆菌的β-半乳糖苷酶的转糖基化反应制得，α-D-Neu5Ac-（2-- > 3）-beta-D-Gal-（1-> 4）-beta-D-GlcNAc-OC6H4NO2-p（9）和alpha-D-Neu5Ac-（2-> 6）-beta-D-Gal -（1-> 4）-beta-D-GlcNAc-OC6H4NO2-p（10）通过重组大鼠α-（2-> 3）-N-唾液酸转移酶和大鼠以等摩尔比的CMP-Neu5Ac有效合成分别为肝α-（2-> 6）-N-唾液酸转移酶。前一种酶还有效地将CMP-Neu5Ac的Neu5Ac残基转移到OH-3在β-D-Gal-（1-> 4）-β-D-Gal-OC6H4NO2-p的非还原末端的位置或β-D-Gal-（1→4）-β-D-Gal-（1→4）-β-D-GlcNAc-OC6H4NO
• Acceptor-dependent regioselectivity of glycosynthase reactions by Streptomyces E383A β-glucosidase
  作者：Magda Faijes、Marc Saura-Valls、Xavi Pérez、Marta Conti、Antoni Planas

  DOI：10.1016/j.carres.2006.04.049

  日期：2006.9

  The normucleophilic mutant E383A beta-glucosidase from Streptomyces sp. has proven to be an efficient glycosynthase enzyme, catalyzing the condensation of alpha-glucosyl and alpha-galactosyl fluoride donors to a variety of acceptors. The enzyme has maximal activity at 45 degrees C, and a pH-dependence reflecting general base catalysis with an apparent kinetic pK(a) of 7.2. The regioselectivity of the new glycosidic linkage depends unexpectedly on the acceptor substrate. With aryl monosaccharide acceptors, beta-(1 -> 3) disaccharides are obtained in good to excellent yields, thus expanding the synthetic products available with current exo-glycosynthases. With xylopyranosyl acceptor, regioselectivity is poorer and results in the formation of a mixture of beta-(1 -> 3) and beta-(1 -> 4) linkages. In contrast, disaccharide acceptors produce exclusively beta-(1 -> 4) linkages. Therefore, the presence of a glycosyl unit in subsite +II redirects regioselectivity from beta-(1 -> 3) to beta-(1 -> 4). To improve operational performance, the E383A mutant was immobilized on a Ni(2+)-chelating Sepharose resin. Immobilization did not increase stability to pH and organic solvents, but the operational stability and storage stability were clearly enhanced for recycling and scaling-up. (c) 2006 Elsevier Ltd. All rights reserved.
• Optimised N-acetyl-d-lactosamine synthesis using Thermus thermophilus β-galactosidase in bio-solvents
  作者：Manuel Sandoval、Concepción Civera、José Berenguer、Francisco García-Blanco、María J. Hernaiz

  DOI：10.1016/j.tet.2012.11.053

  日期：2013.1

  Synthesis of N-acetyl-D-lactosamine (Gal-beta[1 -> 4]GlcNAc, LacNAc) catalyzed by beta-galactosidase from Thermus thermophilus (TTP0042) is affected by side reactions that give as result very low yields (about 20%) of LAcNAc when the reaction is performed in buffer. The process is improved (up to 91% of disaccharide yield) when the reaction takes place in the presence of solvents from biomass (bio-solvents) at 2.0 M concentration. Most of the solvents tested increased the LacNAc synthesis and reduced the undesired side reactions. In order to understand the possible effects of these solvents over the enzyme regioselectivity, we developed a conformational study of the enzyme structure in the presence of a selected bio-solvent by circular dichroism and fluorescence. According to this study, we were able to conclude that the presence of bio-solvents in the reaction media modifies the enzyme secondary and tertiary structure and this may be the cause of the regioselectivity changes observed in the trans-glycosylation reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of p-nitrophenyl 3-O-β-d-galactopyranosyl-β-d-galactopyranoside and p-nitrophenyl 3-O-α-d-galactopyranosyl-β-d-galactopyranoside
  作者：Saeed A. Abbas、Joseph J. Barlow、Khushi L. Matta

  DOI：10.1016/s0008-6215(00)81003-4

  日期：1982.3

  3:1. The structures of 4 , 6 , 8 , and 10 were evidenced by their respective 1 H-n.m.r. spectra. O -Deacetylation of 4 and 6 afforded, respectively, p -nitrophenyl 3- O -α- d -galactopyranosyl-β- d -galactopyranoside ( 5 ) and p -nitrophenyl 3- O -β- d -galactopyranosyl-β- d -galactopyranoside ( 7 ). O -Deacylation of 8 and 10 furnished the disaccharide derivatives ( 9 and 11 ). Cleavage of the benzylidene

  摘要对硝基苯基2,4,6-三-O-乙酰基-β-d-吡喃半乳糖苷（2）与2,3,4,6-四-O-乙酰基-α-d的糖基化反应（氰化汞催化）在乙腈中的-半乳糖基吡喃糖基溴化物以几乎相等的比例提供α-（1→3）-和β-（1→3）连接的二糖七乙酸酯（分别为4和6）。对-硝基苯基2-O-苯甲酰基-4,6-O-亚苄基-β-d-吡喃半乳糖苷（3）的类似糖基化反应产生了β-（1→3）-和α-（1→3）-相连，以3：1的比例完全保护的二糖衍生物（分别为8和10）。4，6，8和10的结构由它们各自的1 Hn.mr光谱证明。4和6的O-脱乙酰基分别提供对-硝基苯基3- O-α-d-吡喃半乳糖基-β-d-吡喃半乳糖苷（5）和对-硝基苯基3- O-β-d-吡喃半乳糖基-β-d-半乳糖吡喃糖苷（7）。8和10的O-脱酰作用提供了二糖衍生物（9和11）。9和11的亚苄基的切割分别给出了二糖7和5。5，7，9和11的结构是通过13
• Chemoenzymatic synthesis of spacer-linked oligosaccharides for the preparation of neoglycoproteins
  作者：Raul Gonzalez Lio、Joachim Thiem

  DOI：10.1016/s0008-6215(99)00073-7

  日期：1999.4

  In the present work, the combination of chemical and enzymatic methods to obtain neoglycoproteins is described. Three bovine serum albumin (BSA)-conjugates, BSA-[GalNAc alpha-], BSA-[Gal(beta 1-3)GalNAc(alpha-], and BSA-[Neu5Ac(alpha 2-3)Gal(beta 1-3)GalNAc(alpha-], were prepared, alpha GalNAc derivatives were galactosylated employing crude P-galactosidase from bovine testes. The use of oversaturated donor solutions (pNP beta Gal) enhanced the yields up to 60%. This method was verified using divalent structures as accepters, that rendered di- and tri-galactosylated products. Further treatment of the disaccharides with CMP-Neu5Ac and alpha 2-3 sialyltransferase from pork liver led to formation of trisaccharides. Finally, mono-, di-, and trisaccharides were coupled to BSA employing a thiolic group introduced into the protein for Michael addition to a maleinimide group in the spacer-ann of the saccharide components. The results were monitored by HPLC and MALDI-TOF. (C) 1999 Elsevier Science Ltd. All rights reserved.