O-α-D-galactosyl-(1,6)-O-β-D-galactosyl-(1,4)-D-glucose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-α-D-galactosyl-(1,6)-O-β-D-galactosyl-(1,4)-D-glucose
• 英文别名: α-D-galactopyranosyl(1->6)-β-D-galactopyranosyl-(1->4)-D-glucopyranose；α-D-Galp-(1->6)-β-D-Galp-(1->4)-D-Glcp-OH；α-Galp-(1->6)-β-Galp-(1->4)-Glcp；Gal(a1-6)Gal(b1-4)Glc；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: OWEGMIWEEQEYGQ-VKGHIWHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  4-硝基苯基-α-D-吡喃半乳糖苷 、 乳糖 在 recombinant Aspergillus nidulans FGSC GH36 α-galactosidase 作用下， 反应 3.0h， 以38%的产率得到O-α-D-galactosyl-(1,6)-O-β-D-galactosyl-(1,4)-D-glucose
  参考文献：
  名称：

  糖苷水解酶家族36的构巢曲霉α-半乳糖苷酶通过转糖基化催化α-半乳糖低聚糖的形成

  摘要：

  来自构巢曲霉（AglC）的α-半乳糖苷酶属于系统发育簇，包含糖苷水解酶家族36（GH36）的真核α-半乳糖苷酶和α-半乳糖寡糖合酶。重组AglC在大肠杆菌中以His-tag融合形式高产量（0.65 g·L -1培养）产生，催化40 m m 4-硝基苯酚α- d-吡喃半乳糖苷具有α-（1→6）区域选择性的高效转糖基化作用，蜜二糖棉子糖或，产生4-硝基苯酚α-收率的37-74％d -Gal p - （1→6） - d -Gal p，α- d -Gal p - （1→6）-α- d-Gal p - （1→6） - d -Glc p和α- d -Gal p - （1→6）-α- d -Gal p - （1→6） - d -Glc p - （α1→β2 ）-d- Fru f（水苏糖）。此外，在10个候选单糖受体（400 m m）和供体4-硝基苯酚α- d-吡喃半乳糖苷（40 m m）中，还获得了由半

  DOI：

  10.1111/j.1742-4658.2010.07763.x

文献信息

• Transgalactosylation Catalyzed by<i>α</i>-Galactosidase from<i>Candida guilliermondii</i>H-404
  作者：Hiroyuki Hashimoto、Chie Katayama、Masaru Goto、Tatsuyuki Okinaga、Sumio Kitahata

  DOI：10.1271/bbb.59.619

  日期：1995.1

  The thermostable α-galactosidase from Candida guilliermondii H-404 synthesized self-transfer products in the absence of a suitable acceptor. The main self-transfer product, using melibiose as a donor substrate, was O-α-D-galactosyl-(1,6)-O-α-D-galactosyl-(1,6)-D-glucose. This enzyme had a wide acceptor specificity. D-Glucose, D-galactose, maltose, maltitol, and 1,4-butandiol were the most effective acceptors in the transgalactosylation catalyzed by this enzyme. The enzyme could also transfer α-galactosyl residues to pentoses (L-arabinose, D-xylose, and D-ribose) and methyl pentoses (D-fucose and L-rhamnose). The main transfer products to lactose, maltose, and sucrose as acceptors were identified as O-α-D-galactosyl-(1,6)-O-β-D-galactosyl-(1,4)-D-glucose, O-α-D-galactosyl-(1,6)-O-α-D-glucosyl-(1,4)-D-glucose, and O-α-D-galactosyl-(1,6)-O-α-D-glucosyl-(1,2)-β-D-fructoside (raffinose), respectively.

  来自Candida guilliermondii H-404的热稳定α-半乳糖苷酶在缺乏合适受体的情况下合成了自转移产物。主要自转移产物是以蜜二糖为供体底物的情况下，形成的O-α-D-半乳糖基-(1,6)-O-α-D-半乳糖基-(1,6)-D-葡萄糖。该酶具有广泛的受体特异性。在由该酶催化的转半乳糖作用中，D-葡萄糖、D-半乳糖、麦芽糖、麦芽糖醇和1,4-丁二醇是最有效的受体。该酶还能将α-半乳糖基转移至戊糖（L-阿拉伯糖、D-木糖和D-核糖）和甲基戊糖（D-岩藻糖和L-鼠李糖）。以乳糖、麦芽糖和蔗糖为受体时，主要转移产物分别被鉴定为O-α-D-半乳糖基-(1,6)-O-β-D-半乳糖基-(1,4)-D-葡萄糖、O-α-D-半乳糖基-(1,6)-O-α-D-葡萄糖基-(1,4)-D-葡萄糖和O-α-D-半乳糖基-(1,6)-O-α-D-葡萄糖基-(1,2)-β-D-果糖苷（棉子糖）。
• 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.
• Aspergillus nidulansα-galactosidase of glycoside hydrolase family 36 catalyses the formation of α-galacto-oligosaccharides by transglycosylation
  作者：Hiroyuki Nakai、Martin J. Baumann、Bent O. Petersen、Yvonne Westphal、Maher Abou Hachem、Adiphol Dilokpimol、Jens Ø. Duus、Henk A. Schols、Birte Svensson

  DOI：10.1111/j.1742-4658.2010.07763.x

  日期：2010.9

  α‐galactosidase from Aspergillus nidulans (AglC) belongs to a phylogenetic cluster containing eukaryotic α‐galactosidases and α‐galacto‐oligosaccharide synthases of glycoside hydrolase family 36 (GH36). The recombinant AglC, produced in high yield (0.65 g·L−1 culture) as His‐tag fusion in Escherichia coli, catalysed efficient transglycosylation with α‐(1→6) regioselectivity from 40 mm 4‐nitrophenol α

  来自构巢曲霉（AglC）的α-半乳糖苷酶属于系统发育簇，包含糖苷水解酶家族36（GH36）的真核α-半乳糖苷酶和α-半乳糖寡糖合酶。重组AglC在大肠杆菌中以His-tag融合形式高产量（0.65 g·L -1培养）产生，催化40 m m 4-硝基苯酚α- d-吡喃半乳糖苷具有α-（1→6）区域选择性的高效转糖基化作用，蜜二糖棉子糖或，产生4-硝基苯酚α-收率的37-74％d -Gal p - （1→6） - d -Gal p，α- d -Gal p - （1→6）-α- d-Gal p - （1→6） - d -Glc p和α- d -Gal p - （1→6）-α- d -Gal p - （1→6） - d -Glc p - （α1→β2 ）-d- Fru f（水苏糖）。此外，在10个候选单糖受体（400 m m）和供体4-硝基苯酚α- d-吡喃半乳糖苷（40 m m）中，还获得了由半