β-D-galactopyranosyl-(1->3)-α-D-glucopyranosyl-(1<->2)-β-D-fructofuranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranosyl-(1->3)-α-D-glucopyranosyl-(1<->2)-β-D-fructofuranoside
• 英文别名: β-D-galactopyranosyl-(1→3)-α-D-glucopyranosyl-(1↔2)-β-D-fructofuranoside；β-D-Galp-(1->3)-α-D-Glcp-(1<->2)-β-D-Fruf；β-D-Galp-(1->3)-α-D-Glcp-(1->2)-β-D-Fruf；lactosaccharose；(2S,3R,4S,5R,6R)-2-(((2R,3R,4S,5R,6R)-2-(((2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: AEVXMUQAEMWBMR-JAHJXKICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  34
• 可旋转键数：
  8
• 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

• 作为反应物：
  描述：

  乙酸酐 、 β-D-galactopyranosyl-(1->3)-α-D-glucopyranosyl-(1<->2)-β-D-fructofuranoside 在 吡啶 作用下， 生成 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-acetyl-α-D-glucopyranosyl 1,3,4,6-tetra-O-acetyl-β-D-fructofuranoside
  参考文献：
  名称：

  使用重组α-和β-半乳糖苷酶和新型供体底物进行转糖基化

  摘要：

  重组α-和β-半乳糖苷酶可以大量制备，用于化学方法合成与营养方法相关的糖基化低聚糖。来自大肠杆菌的α-半乳糖苷酶RafA，来自嗜热嗜热脂肪芽孢杆菌KVE39的另一种嗜热α-半乳糖苷酶AgaB以及来自嗜热栖热菌TH 125的嗜热β-半乳糖苷酶BglT可以分别用于α-糖基化和β-糖基化。利用模型结构以及蔗糖，异麦芽糖醇和异麦芽酮糖，研究了立体和区域特异性。此外，合成，采用了具有结构变化和不同离去基团的许多修饰的供体结构，并将其与经典的供体进行了这些转糖基化的比较。

  DOI：

  10.1016/j.carres.2014.05.005
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 β-galactosidase BglT 、 氨 作用下， 以 甲醇 、 aq. phosphate buffer 为溶剂， 反应 31.0h， 生成 β-D-galactopyranosyl-(1->3)-α-D-glucopyranosyl-(1<->2)-β-D-fructofuranoside
  参考文献：
  名称：

  使用重组α-和β-半乳糖苷酶和新型供体底物进行转糖基化

  摘要：

  重组α-和β-半乳糖苷酶可以大量制备，用于化学方法合成与营养方法相关的糖基化低聚糖。来自大肠杆菌的α-半乳糖苷酶RafA，来自嗜热嗜热脂肪芽孢杆菌KVE39的另一种嗜热α-半乳糖苷酶AgaB以及来自嗜热栖热菌TH 125的嗜热β-半乳糖苷酶BglT可以分别用于α-糖基化和β-糖基化。利用模型结构以及蔗糖，异麦芽糖醇和异麦芽酮糖，研究了立体和区域特异性。此外，合成，采用了具有结构变化和不同离去基团的许多修饰的供体结构，并将其与经典的供体进行了这些转糖基化的比较。

  DOI：

  10.1016/j.carres.2014.05.005

文献信息

• First Direct Glycosylation of Unprotected Nonreducing Mono- and Disaccharides
  作者：Andreas Steinmann、Julian Thimm、Joachim Thiem

  DOI：10.1002/ejoc.200700504

  日期：2007.11

  glycosyl acceptors is reported by random glycosylation leading to all possible regioisomers. For such systems conventional glycosylation methods such as Koenigs–Knorr glycosylation, Schmidt's trichloroacetimidate glycosylation and reactions employing glycosyl fluoride donors fail entirely. Starting from unprotected nonreducing saccharides, the glycosylation of β-glucosylated and β-galactosylated monosaccharides

  完全无保护的糖基受体的第一个单步随机糖基化方法报告通过随机糖基化导致所有可能的区域异构体。对于此类系统，传统的糖基化方法，例如 Koenigs-Knorr 糖基化、Schmidt 的三氯乙酰亚胺糖基化和使用糖基氟供体的反应完全失败。从未受保护的非还原糖开始，研究了 β-葡萄糖基化和 β-半乳糖基化单糖（Glc、Gal）、对称二糖（例如 α,α-海藻糖）以及不对称二糖（例如蔗糖）的糖基化。检查了碱类型和浓度的影响。生成了几个二糖和三糖文库。所有区域异构体以大致相等的比例形成，用快速柱色谱法实现部分分离。尽管与经典的保护基化学相比，总体产率似乎较低，但这种合成努力可能更胜一筹，尤其是在获得更高的糖类方面。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Synthesis of oligosaccharides as potential novel food components and upscaled enzymatic reaction employing the β-galactosidase from bovine testes
  作者：Sven Schröder、Ulja Schmidt、Joachim Thiem、Jörg Kowalczyk、Markwart Kunz、Manfred Vogel

  DOI：10.1016/j.tet.2004.01.029

  日期：2004.3

  The β-galactosidase from bovine testes (EC 3.2.1.23) promotes the transfer of a galactose unit to glucose or galactose-containing residues in manifold derivatives, establishing β1→3 linkages.

  牛睾丸的β-半乳糖苷酶（EC 3.2.1.23）促进半乳糖单元向歧管衍生物中的葡萄糖或含半乳糖的残基转移，从而建立β1→3键。
• Effective Enzymatic Synthesis of Lactosucrose and Its Analogues by β-<scp>d</scp>-Galactosidase from <i>Bacillus circulans</i>
  作者：Wei Li、Xiaoli Xiang、Shufen Tang、Bing Hu、Lin Tian、Yi Sun、Hong Ye、Xiaoxiong Zeng

  DOI：10.1021/jf9002494

  日期：2009.5.13

  In the present study, beta-D-galactosidase from Bacillus circulans was proved to be a suitable biocatalyst for the production of lactosucrose (beta-D-Galp-(1 -> 4)-alpha-D-Glcp-(1 -> 2)-beta-D-Fruf, I) and its analogues from lactose and sucrose. During the hydrolysis of lactose, the formation of four transfer products was followed by high performance liquid chromatography with refraction index detector. In addition, the transfer products were isolated from the reaction mixture and identified to be I, beta-D-Galp-(1 -> 3)-alpha-D-Glcp-(1 -> 2)-beta-D-Fruf (II), beta-D-Galp-(1 -> 4)-beta-D-Galp-(1 -> 4)-alpha,beta-D-Glcp (III), and beta-D-Galp-(1 -> 4)-beta-D-Galp-(1 -> 4)-alpha-D-Glcp-(1 -> 2)-beta-D-Fruf (IV) by mass spectrometry with an electrospray ionization source and nuclear magnetic resonance spectroscopy. The order for the production of the transfer products was III > I > IV > II in the initial stage of the reaction, and the same relationship was also observed for the hydrolytic rates of transfer products. Furthermore, the effects of synthetic conditions including reaction temperature, reaction time, concentration of substrate, molar ratio of donor/acceptor, and enzyme concentration on the formation of transfer products were examined. We found that the optimal synthetic conditions were different for the production of I and II. Under the optimal conditions, the amount of total transfer products kept increasing during the early 4 h incubation, and a maximum yield of 146 g/L for total transfer products was obtained at 4 h of reaction.