β-D-Galp-(1→3)-β-D-Glcp | 909891-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-Galp-(1→3)-β-D-Glcp
• 英文别名: β-D-galactopyranosyl-(1->3)-β-D-glucopyranoside；β-D-Galp-(1->3)-β-D-Glcp；3-O-beta-D-Galactopyranosyl-beta-D-glucopyranose；(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2,3,5-triol
• CAS: 909891-53-8
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: QIGJYVCQYDKYDW-MESDJYPDSA-N

物化性质

• 沸点：
  690.5±55.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  phenyl β-D-galactopyranosyl-(1->3)-1-thio-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 为溶剂， 反应 0.5h， 生成 β-D-Galp-(1→3)-β-D-Glcp 、 β-D-galactopyranosyl-(1->3)-α-D-glucopyranoside
  参考文献：
  名称：

  Engineering of glucoside acceptors for the regioselective synthesis of β-(1→3)-disaccharides with glycosynthases

  摘要：

  Glycosynthase mutants obtained from Thermotoga maritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1 -> 3)-beta-D-Glcp and aryl beta-D-Glcp-(1 -> 3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-D-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-D-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1 -> 3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.07.018

文献信息

• Engineering of the <i>Bacillus circulans</i> β-Galactosidase Product Specificity
  作者：Huifang Yin、Tjaard Pijning、Xiangfeng Meng、Lubbert Dijkhuizen、Sander S. van Leeuwen

  DOI：10.1021/acs.biochem.7b00032

  日期：2017.2.7

  the multiple biological functions of hMOS, it is important to broaden the variety of GOS structures. In this study, residue R484 near +1 subsite of the C-terminally truncated β-galactosidase from Bacillus circulans (BgaD-D) was subjected to site saturation mutagenesis. Especially the R484S and R484H mutant enzymes displayed significantly altered enzyme specificity, leading to a new type of GOS mixture

  微生物β-半乳糖苷酶在工业上被广泛用作从乳糖生产益生元低聚半乳糖（GOS）的生物催化剂。GOS混合物在婴儿配方食品中用作有益的添加剂，以模仿人乳寡糖（hMOS）的益生元作用。GOS混合物的结构多样性明显低于hMOS。由于这种结构复杂性被认为是hMOS多种生物学功能的基础，因此拓宽GOS结构的多样性非常重要。在这项研究中，来自圆形芽孢杆菌C末端截短的β-半乳糖苷酶+1亚位点附近的残基R484（BgaD-D）进行位点饱和诱变。特别是R484S和R484H突变酶显示出显着改变的酶特异性，从而导致一种新型的GOS混合物，其结构和键合类型也发生了改变。这些突变酶产生的GOS混合物含有14种在野生型GOS混合物中不存在的结构。其中10个是全新的结构。这些突变酶产生的GOS包含（β1→3）和（β1→4）键的组合，而野生型酶对（β1→4）键具有明显的偏好。三糖β- d -Gal p-（1→3）-β- d-
• Engineering of glucoside acceptors for the regioselective synthesis of β-(1→3)-disaccharides with glycosynthases
  作者：Zsuzanna Marton、Vinh Tran、Charles Tellier、Michel Dion、Jullien Drone、Claude Rabiller

  DOI：10.1016/j.carres.2008.07.018

  日期：2008.11

  Glycosynthase mutants obtained from Thermotoga maritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1 -> 3)-beta-D-Glcp and aryl beta-D-Glcp-(1 -> 3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-D-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-D-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1 -> 3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively. (C) 2008 Elsevier Ltd. All rights reserved.